From f05b8f44bcdb293736c4084d9f92adce2295cf7a Mon Sep 17 00:00:00 2001
From: Braedon Saunders <braedonsaunders@users.noreply.github.com>
Date: Thu, 26 Feb 2026 00:34:55 -0500
Subject: [PATCH] chore: commit local workspace changes

---
 packages/app/src/context/orchestrate.tsx      |  28 +
 packages/app/src/pages/deploy.tsx             | 770 +++++++++++-------
 packages/oneshot/src/deploy/session.ts        | 123 ++-
 packages/oneshot/src/orchestrator/index.ts    | 101 ++-
 .../orchestrator/runtime/langgraph-engine.ts  | 377 ++++++++-
 .../src/orchestrator/runtime/recovery.ts      | 105 +++
 .../src/orchestrator/runtime/verification.ts  | 116 ++-
 .../src/orchestrator/runtime/workflow.ts      |  35 +-
 .../orchestrator/runtime/worktree-ingest.ts   |  47 +-
 .../orchestrator/checklist-expansion.test.ts  |  38 +
 .../test/orchestrator/recovery-errors.test.ts |  37 +
 .../replan-decision-sanitization.test.ts      | 107 +++
 .../test/orchestrator/verification.test.ts    |  45 +
 13 files changed, 1572 insertions(+), 357 deletions(-)
 create mode 100644 packages/oneshot/src/orchestrator/runtime/recovery.ts
 create mode 100644 packages/oneshot/test/orchestrator/checklist-expansion.test.ts
 create mode 100644 packages/oneshot/test/orchestrator/recovery-errors.test.ts

diff --git a/packages/app/src/context/orchestrate.tsx b/packages/app/src/context/orchestrate.tsx
index b78ab44..9a1ebbb 100644
--- a/packages/app/src/context/orchestrate.tsx
+++ b/packages/app/src/context/orchestrate.tsx
@@ -210,10 +210,20 @@ export interface LocalDeployRequest {
   error?: string
 }
 
+export interface LocalDeployOpenTarget {
+  type: "url" | "path"
+  target: string
+  label?: string
+  app?: string
+  autoOpenedAt?: number
+  autoOpenError?: string
+}
+
 export interface LocalDeployState {
   status: "idle" | "running" | "passed" | "failed"
   trigger?: "manual" | "finalize"
   url?: string
+  openTarget?: LocalDeployOpenTarget
   requestedAt?: number
   startedAt?: number
   completedAt?: number
@@ -722,6 +732,23 @@ function parseLocalDeployRequest(value: unknown): LocalDeployRequest | undefined
   }
 }
 
+function parseLocalDeployOpenTarget(value: unknown): LocalDeployOpenTarget | undefined {
+  if (!isRecord(value)) return undefined
+  const type = value.type === "url" || value.type === "path"
+    ? value.type
+    : undefined
+  const target = asString(value.target)
+  if (!type || !target) return undefined
+  return {
+    type,
+    target,
+    label: asString(value.label),
+    app: asString(value.app),
+    autoOpenedAt: asNumber(value.autoOpenedAt),
+    autoOpenError: asString(value.autoOpenError),
+  }
+}
+
 function parseLocalDeploy(value: unknown): LocalDeployState | undefined {
   if (!isRecord(value)) return undefined
   const status = asLocalDeployStatus(value.status)
@@ -811,6 +838,7 @@ function parseLocalDeploy(value: unknown): LocalDeployState | undefined {
     status,
     trigger,
     url: asString(value.url),
+    openTarget: parseLocalDeployOpenTarget(value.openTarget),
     requestedAt: asNumber(value.requestedAt),
     startedAt: asNumber(value.startedAt),
     completedAt: asNumber(value.completedAt),
diff --git a/packages/app/src/pages/deploy.tsx b/packages/app/src/pages/deploy.tsx
index b30711c..d915883 100644
--- a/packages/app/src/pages/deploy.tsx
+++ b/packages/app/src/pages/deploy.tsx
@@ -6,6 +6,12 @@ import type { LocalPTY } from "@/context/terminal"
 import { useOrchestrate } from "@/context/orchestrate"
 import { usePlatform } from "@/context/platform"
 import { useSDK } from "@/context/sdk"
+import {
+  openDeployOpenTarget,
+  resolveDeployInvocationOpenTarget,
+  resolveDeployOpenTarget,
+  type DeployOpenTarget as DeployResolvedOpenTarget,
+} from "@/lib/deploy-open-target"
 
 type DeployToolName =
   | "terminal_exec"
@@ -218,8 +224,6 @@ const ROLE_STREAM_STYLE: Record<DeployMessageRole, { dot: string; label: string;
   },
 }
 
-const TOOL_PANE_WIDTH = "clamp(340px, 34vw, 620px)"
-
 function formatDate(value?: number): string {
   if (!value) return "-"
   return new Date(value).toLocaleString()
@@ -318,7 +322,34 @@ type LaunchGuide = {
   source: "run" | "session" | "handoff" | "heuristic"
 }
 
-type DeployOpenTarget = "web_view" | "terminal_view" | "external"
+type DeployOpenMode = "web_view" | "terminal_view" | "external"
+type DeployViewMode = "surface" | "chat"
+
+type DeploySurface =
+  | { kind: "web"; url: string; source: "preview" | "open_target" }
+  | { kind: "terminal"; pty: LocalPTY; source: "live_pty" }
+  | { kind: "external"; target?: DeployResolvedOpenTarget; source: "open_target" }
+
+function parseDeployOpenMode(value: unknown): DeployOpenMode | undefined {
+  if (value === "web_view" || value === "terminal_view" || value === "external") return value
+  return undefined
+}
+
+function invocationIsOpenAction(invocation: DeployToolInvocation): boolean {
+  const meta = invocation.output?.meta
+  if (!meta || typeof meta !== "object") return false
+  return (meta as Record<string, unknown>).openAction === true
+}
+
+function invocationOpenMode(invocation: DeployToolInvocation | undefined): DeployOpenMode | undefined {
+  if (!invocation) return undefined
+  const inputTarget = parseDeployOpenMode(invocation.input?.target)
+  if (inputTarget) return inputTarget
+  const meta = invocation.output?.meta
+  if (!meta || typeof meta !== "object") return undefined
+  const record = meta as Record<string, unknown>
+  return parseDeployOpenMode(record.target)
+}
 
 function extractFirstUrl(value: string): string | undefined {
   const match = value.match(/https?:\/\/[^\s)]+/i)
@@ -455,7 +486,7 @@ function InvocationWidget(props: {
             when={!compact}
             fallback={
               <div class="rounded-md border border-border-weak-base/80 bg-background-base/80 px-2 py-1 text-[10px] text-text-weak">
-                Table output captured ({table?.rows.length ?? 0} rows). Open Flight Deck for full view.
+                Table output captured ({table?.rows.length ?? 0} rows). Open Runtime view for full table details.
               </div>
             }
           >
@@ -575,9 +606,10 @@ export default function DeployPage() {
   const [openingApp, setOpeningApp] = createSignal(false)
 
   const [chatInput, setChatInput] = createSignal("")
-  const [runLinkInput, setRunLinkInput] = createSignal("")
-  const [activeInvocationId, setActiveInvocationId] = createSignal<string | undefined>(undefined)
-  const [paneDismissed, setPaneDismissed] = createSignal(true)
+  const [viewMode, setViewMode] = createSignal<DeployViewMode>("chat")
+  const [lastExternalTarget, setLastExternalTarget] = createSignal<DeployResolvedOpenTarget | undefined>(undefined)
+  const [externalOpenError, setExternalOpenError] = createSignal<string | undefined>(undefined)
+  const [autoLinkedKey, setAutoLinkedKey] = createSignal<string | undefined>(undefined)
   const [launchGuideExpanded, setLaunchGuideExpanded] = createSignal(true)
 
   let chatScrollRef: HTMLDivElement | undefined
@@ -689,27 +721,77 @@ export default function DeployPage() {
     return undefined
   })
 
-  const latestInvocation = createMemo(() => {
+  const latestRunningInvocation = createMemo(() => {
     const list = session()?.invocations ?? []
-    if (list.length === 0) return undefined
-    return list[list.length - 1]
+    for (let index = list.length - 1; index >= 0; index--) {
+      if (list[index]?.status === "running") return list[index]
+    }
+    return undefined
   })
 
-  const latestRunningInvocation = createMemo(() => {
+  const latestOpenInvocation = createMemo(() => {
     const list = session()?.invocations ?? []
     for (let index = list.length - 1; index >= 0; index--) {
-      if (list[index]?.status === "running") return list[index]
+      const invocation = list[index]
+      if (invocation && invocationIsOpenAction(invocation)) return invocation
     }
     return undefined
   })
 
-  const activeInvocation = createMemo(() => {
-    const focused = activeInvocationId() ? invocationById().get(activeInvocationId()!) : undefined
-    if (focused) return focused
-    return latestRunningInvocation() ?? latestInvocation()
+  const latestLiveTerminal = createMemo(() => {
+    const list = session()?.invocations ?? []
+    for (let index = list.length - 1; index >= 0; index--) {
+      const invocation = list[index]
+      if (!invocation) continue
+      const pty = invocationLivePty(invocation)
+      if (pty) return pty
+    }
+    return undefined
+  })
+
+  const openMode = createMemo(() => invocationOpenMode(latestOpenInvocation()))
+
+  const deployOpenTarget = createMemo<DeployResolvedOpenTarget | undefined>(() => {
+    const fromInvocation = resolveDeployInvocationOpenTarget(latestOpenInvocation()?.output, {
+      includePreviewFallback: false,
+    })
+    if (fromInvocation) return fromInvocation
+    const fromRun = resolveDeployOpenTarget(linkedRunLocalDeploy())
+    if (fromRun) return fromRun
+    return lastExternalTarget()
+  })
+
+  const surface = createMemo<DeploySurface | undefined>(() => {
+    const mode = openMode()
+    const url = latestPreviewUrl()
+    const target = deployOpenTarget()
+    const terminal = latestLiveTerminal()
+
+    if (mode === "external") return { kind: "external", target, source: "open_target" }
+    if (mode === "web_view") {
+      if (url) return { kind: "web", url, source: "preview" }
+      if (target?.type === "url") return { kind: "web", url: target.target, source: "open_target" }
+      return terminal ? { kind: "terminal", pty: terminal, source: "live_pty" } : undefined
+    }
+    if (mode === "terminal_view") {
+      if (terminal) return { kind: "terminal", pty: terminal, source: "live_pty" }
+      if (url) return { kind: "web", url, source: "preview" }
+    }
+
+    if (url) return { kind: "web", url, source: "preview" }
+    if (terminal) return { kind: "terminal", pty: terminal, source: "live_pty" }
+    if (target?.type === "url") return { kind: "web", url: target.target, source: "open_target" }
+    if (target) return { kind: "external", target, source: "open_target" }
+    return undefined
   })
 
-  const toolPaneOpen = createMemo(() => !paneDismissed() && !!activeInvocation())
+  const surfaceLabel = createMemo(() => {
+    const value = surface()
+    if (!value) return "No runtime surface detected yet"
+    if (value.kind === "web") return "Surface: Webview"
+    if (value.kind === "terminal") return "Surface: Interactive terminal"
+    return "Surface: External app"
+  })
 
   const routedFailureCount = createMemo(
     () =>
@@ -784,8 +866,6 @@ export default function DeployPage() {
         throw new Error("Invalid deploy session response")
       }
       setSession(parsed)
-      setActiveInvocationId(undefined)
-      setPaneDismissed(true)
       return parsed
     } finally {
       setCreatingSession(false)
@@ -796,8 +876,10 @@ export default function DeployPage() {
     const token = ++initializeToken
     setInitializing(true)
     setSession(undefined)
-    setActiveInvocationId(undefined)
-    setPaneDismissed(true)
+    setViewMode("chat")
+    setLastExternalTarget(undefined)
+    setExternalOpenError(undefined)
+    setAutoLinkedKey(undefined)
 
     try {
       await loadToolsState()
@@ -810,10 +892,8 @@ export default function DeployPage() {
 
       if (latest) {
         setSession(latest)
-        setRunLinkInput(latest.linkedRunId ?? activeRunId())
       } else {
         setSession(undefined)
-        setRunLinkInput(activeRunId())
       }
     } catch (error) {
       if (token !== initializeToken) return
@@ -864,7 +944,6 @@ export default function DeployPage() {
       const next = parseSession(payload)
       if (!next) throw new Error("Invalid deploy session response")
       setSession(next)
-      setRunLinkInput(next.linkedRunId ?? "")
     } catch (error) {
       showToast({
         title: "Run link update failed",
@@ -882,17 +961,13 @@ export default function DeployPage() {
 
   createEffect(() => {
     const current = session()
-    if (!current) return
-    if (runLinkInput().trim()) return
-    setRunLinkInput(current.linkedRunId ?? activeRunId())
-  })
-
-  createEffect(() => {
-    const running = latestRunningInvocation()
-    if (!running) return
-    if (activeInvocationId() !== running.id) {
-      setActiveInvocationId(running.id)
-    }
+    const runId = activeRunId()
+    if (!current || !runId || linkingRun()) return
+    if (current.linkedRunId?.trim() === runId) return
+    const key = `${current.id}:${runId}`
+    if (autoLinkedKey() === key) return
+    setAutoLinkedKey(key)
+    void linkRun(runId)
   })
 
   createEffect(() => {
@@ -916,6 +991,20 @@ export default function DeployPage() {
     scrollChatToBottom()
   })
 
+  createEffect((previousStatus?: DeploySessionStatus) => {
+    const status = session()?.status
+    if (status === "passed" && previousStatus !== "passed") {
+      void openApp({ silent: true })
+    }
+    return status
+  })
+
+  createEffect(() => {
+    if (!surface()) return
+    if (session()?.status !== "passed") return
+    setViewMode("surface")
+  })
+
   onCleanup(() => {
     if (chatScrollFrame !== undefined) cancelAnimationFrame(chatScrollFrame)
   })
@@ -935,7 +1024,7 @@ export default function DeployPage() {
     return map
   })
 
-  async function openApp(): Promise<void> {
+  async function openApp(options: { silent?: boolean } = {}): Promise<void> {
     if (openingApp()) return
     const current = session()
     if (!current) {
@@ -951,6 +1040,36 @@ export default function DeployPage() {
       return
     }
 
+    const fallbackTarget = deployOpenTarget()
+    const hasServerOpenTarget = Boolean(
+      current.launchUrl?.trim() ||
+      (current.launchCommand?.length ?? 0) > 0 ||
+      latestPreviewUrl() ||
+      launchGuide()?.openUrl,
+    )
+    if (!hasServerOpenTarget && fallbackTarget) {
+      if (fallbackTarget.type === "path") {
+        setExternalOpenError(undefined)
+        try {
+          await openDeployOpenTarget({ platform, target: fallbackTarget })
+          setLastExternalTarget(fallbackTarget)
+          setViewMode("surface")
+        } catch (error) {
+          const message = error instanceof Error ? error.message : String(error)
+          setExternalOpenError(message)
+          if (!options.silent) {
+            showToast({
+              title: "Open failed",
+              description: message,
+            })
+          }
+        }
+        return
+      }
+      setViewMode("surface")
+      return
+    }
+
     setOpeningApp(true)
     try {
       const payload = await apiJson<unknown>(`/deploy/session/${current.id}/open`, {
@@ -961,10 +1080,11 @@ export default function DeployPage() {
       if (!record) throw new Error("Invalid open response")
 
       const nextSession = parseSession(record.session)
+      let resolvedSession = nextSession
       if (nextSession) {
         setSession(nextSession)
       } else {
-        await refreshSessionById(current.id)
+        resolvedSession = await refreshSessionById(current.id)
       }
 
       const invocationRecord = record.invocation
@@ -974,26 +1094,48 @@ export default function DeployPage() {
         typeof (invocationRecord as { id?: unknown }).id === "string"
           ? (invocationRecord as { id: string }).id
           : undefined
-      if (invocationId) {
-        setActiveInvocationId(invocationId)
-        setPaneDismissed(false)
-      }
+      const invocation = invocationId
+        ? resolvedSession?.invocations.find((entry) => entry.id === invocationId)
+        : undefined
 
-      const target = typeof record.target === "string" ? (record.target as DeployOpenTarget) : "terminal_view"
+      const target = parseDeployOpenMode(record.target) ?? invocationOpenMode(invocation) ?? "terminal_view"
       const openedUrl = typeof record.url === "string" && record.url.trim() ? record.url.trim() : undefined
-      if (openedUrl && (target === "web_view" || target === "external")) {
-        platform.openLink(openedUrl)
+      const openTarget = resolveDeployOpenTarget({
+        openTarget: record.openTarget,
+        url: openedUrl,
+      })
+        ?? resolveDeployInvocationOpenTarget(invocation?.output, { includePreviewFallback: false })
+        ?? resolveDeployOpenTarget(linkedRunLocalDeploy())
+
+      setExternalOpenError(undefined)
+      if (target === "external") {
+        setLastExternalTarget(openTarget)
+        if (openTarget) {
+          await openDeployOpenTarget({
+            platform,
+            target: openTarget,
+          }).catch((error) => {
+            const message = error instanceof Error ? error.message : String(error)
+            setExternalOpenError(message)
+            throw error
+          })
+        }
       }
+      setViewMode("surface")
 
-      showToast({
-        title: "Open complete",
-        description: typeof record.message === "string" ? record.message : undefined,
-      })
+      if (!options.silent) {
+        showToast({
+          title: "Open complete",
+          description: typeof record.message === "string" ? record.message : undefined,
+        })
+      }
     } catch (error) {
-      showToast({
-        title: "Open failed",
-        description: error instanceof Error ? error.message : String(error),
-      })
+      if (!options.silent) {
+        showToast({
+          title: "Open failed",
+          description: error instanceof Error ? error.message : String(error),
+        })
+      }
     } finally {
       setOpeningApp(false)
     }
@@ -1040,8 +1182,7 @@ export default function DeployPage() {
               <div class="min-w-0 flex-1">
                 <div class="text-20-medium text-text-strong">Deploy Agent</div>
                 <div class="mt-1 text-12-regular text-text-weak">
-                  Deploy checks can pass while UX is still broken. Report exact repro steps in chat; widgets stay
-                  compact inline and expand in the flight deck.
+                  Deploy stays linked to the master orchestrator run so failures can trigger intervention and reruns.
                 </div>
               </div>
 
@@ -1073,7 +1214,8 @@ export default function DeployPage() {
                       (!session()?.launchUrl?.trim() &&
                         !(session()?.launchCommand?.length ?? 0) &&
                         !latestPreviewUrl() &&
-                        !launchGuide()?.openUrl)
+                        !launchGuide()?.openUrl &&
+                        !deployOpenTarget())
                     }
                     onClick={() => {
                       void openApp()
@@ -1086,6 +1228,23 @@ export default function DeployPage() {
             </div>
 
             <div class="mt-2 flex flex-wrap items-center gap-2">
+              <span class="rounded-md border border-border-weak-base/80 bg-background-weak-base/40 px-2 py-0.5 text-10-medium text-text-weak">
+                Master run: {activeRunId() || "none"}
+              </span>
+              <span
+                class={`rounded-md border px-2 py-0.5 text-10-medium ${
+                  activeRunId() && session()?.linkedRunId?.trim() === activeRunId()
+                    ? "border-icon-success-base/30 bg-icon-success-base/10 text-icon-success-base"
+                    : "border-icon-warning-base/30 bg-icon-warning-base/10 text-icon-warning-base"
+                }`}
+              >
+                Linked run: {session()?.linkedRunId ?? "none"}
+              </span>
+              <Show when={linkingRun()}>
+                <span class="rounded-md border border-border-weak-base/80 bg-background-weak-base/40 px-2 py-0.5 text-10-medium text-text-weak">
+                  Syncing link...
+                </span>
+              </Show>
               <Show when={session()?.detectedProjectTypes}>
                 {(detected) => (
                   <For each={detected()}>
@@ -1155,287 +1314,304 @@ export default function DeployPage() {
           </div>
 
           <div class="min-h-0 flex-1 overflow-hidden">
-            <div class="flex h-full min-h-0 w-full overflow-hidden">
-              <div class="min-h-0 min-w-0 flex-1 bg-background-base">
-                <div class="flex h-full min-h-0 flex-col">
-                  <div class="border-b border-border-weak-base bg-background-weak-base px-4 py-3">
-                    <div class="text-12-medium text-text-strong">Deploy Chat</div>
-                    <div class="mt-0.5 text-11-regular text-text-weak">
-                      Describe the failure and repro steps. Deploy reruns local checks, and inline widgets can be
-                      expanded into the flight deck.
+            <div class="flex h-full min-h-0 w-full flex-col overflow-hidden">
+              <div class="shrink-0 border-b border-border-weak-base bg-background-weak-base px-4 py-2.5">
+                <div class="flex flex-wrap items-center gap-2">
+                  <Show when={surface()}>
+                    <Button
+                      size="small"
+                      variant={viewMode() === "surface" ? "secondary" : "ghost"}
+                      class="h-7 px-2.5"
+                      onClick={() => setViewMode("surface")}
+                    >
+                      Runtime
+                    </Button>
+                  </Show>
+                  <Button
+                    size="small"
+                    variant={viewMode() === "chat" ? "secondary" : "ghost"}
+                    class="h-7 px-2.5"
+                    onClick={() => setViewMode("chat")}
+                  >
+                    Chat
+                  </Button>
+                  <span class="text-11-regular text-text-weak">
+                    {surfaceLabel()}
+                  </span>
+                  <Show when={tools().length > 0}>
+                    <span class="ml-auto text-10-regular text-text-weak">Tools: {tools().length}</span>
+                  </Show>
+                </div>
+              </div>
+
+              <Show when={viewMode() === "surface"} fallback={
+                <div class="min-h-0 flex-1 bg-background-base">
+                  <div class="flex h-full min-h-0 flex-col">
+                    <div class="border-b border-border-weak-base bg-background-weak-base px-4 py-3">
+                      <div class="text-12-medium text-text-strong">Deploy Chat</div>
+                      <div class="mt-0.5 text-11-regular text-text-weak">
+                        Describe failures with repro steps. Deploy reruns checks and routes failures back to master.
+                      </div>
                     </div>
-                  </div>
 
-                  <div class="min-h-0 flex-1 overflow-hidden bg-background-base">
-                    <div
-                      ref={(el) => {
-                        chatScrollRef = el
-                      }}
-                      class="relative min-h-0 h-full min-w-0 w-full overflow-y-auto session-scroller"
-                    >
+                    <div class="min-h-0 flex-1 overflow-hidden bg-background-base">
                       <div
-                        role="log"
-                        class="flex min-h-full w-full min-w-0 flex-col gap-4 pb-4 pt-3 px-2 md:max-w-200 md:mx-auto 2xl:max-w-[1000px] md:px-0"
+                        ref={(el) => {
+                          chatScrollRef = el
+                        }}
+                        class="relative min-h-0 h-full min-w-0 w-full overflow-y-auto session-scroller"
                       >
-                        <Show
-                          when={!initializing()}
-                          fallback={
-                            <div class="text-12-regular text-text-weak px-2 md:px-6">
-                              Initializing deploy session...
-                            </div>
-                          }
+                        <div
+                          role="log"
+                          class="flex min-h-full w-full min-w-0 flex-col gap-4 pb-4 pt-3 px-2 md:max-w-200 md:mx-auto 2xl:max-w-[1000px] md:px-0"
                         >
                           <Show
-                            when={session()?.messages.length}
+                            when={!initializing()}
                             fallback={
-                              <div class="text-12-regular text-text-weak px-2 md:px-6 py-4 text-center">
-                                {session()
-                                  ? "No messages yet. Ask the deploy agent to validate this repo."
-                                  : "Deploy thread is initializing. It should appear automatically."}
+                              <div class="text-12-regular text-text-weak px-2 md:px-6">
+                                Initializing deploy session...
                               </div>
                             }
                           >
-                            <For each={session()?.messages ?? []}>
-                              {(message) => {
-                                const invocations = messageInvocationResolver(message)
-                                const style = ROLE_STREAM_STYLE[message.role]
-                                return (
-                                  <div class="min-w-0 w-full px-2 md:px-6">
-                                    <div class="text-13-regular leading-relaxed whitespace-pre-wrap break-words">
-                                      <div class="flex items-center gap-1.5 mb-1">
-                                        <span class={`size-1.5 rounded-full shrink-0 ${style.dot}`} />
-                                        <span class={`text-10-medium uppercase tracking-wider ${style.label}`}>
-                                          {ROLE_LABEL[message.role]}
-                                        </span>
-                                        <span class="text-10-regular text-text-weak ml-auto">
-                                          {formatDate(message.createdAt)}
-                                        </span>
-                                      </div>
-                                      <div class={`${style.body} break-words`}>{message.text}</div>
-
-                                      <Show when={invocations.length > 0}>
-                                        <div class="mt-2.5 flex flex-col gap-2">
-                                          <For
-                                            each={invocations.filter(
-                                              (invocation) =>
-                                                latestMessageByInvocation().get(invocation.id) === message.id,
-                                            )}
-                                          >
-                                            {(invocation) => (
-                                              <div class="rounded-xl border border-border-weak-base/70 bg-background-weak-base/20 p-2">
-                                                <div class="mb-2 flex flex-wrap items-center justify-between gap-1.5">
-                                                  <span
-                                                    class={`inline-flex items-center gap-1.5 rounded-md border px-2 py-1 text-10-medium uppercase tracking-wide ${
-                                                      INVOCATION_STATUS_CLASS[invocation.status]
-                                                    }`}
-                                                  >
-                                                    <span>{TOOL_WIDGET_THEME[invocation.tool].label}</span>
-                                                    <span class="text-[9px] text-text-weak">
-                                                      {invocation.id.slice(-6)}
+                            <Show
+                              when={session()?.messages.length}
+                              fallback={
+                                <div class="text-12-regular text-text-weak px-2 md:px-6 py-4 text-center">
+                                  {session()
+                                    ? "No messages yet. Ask the deploy agent to validate this repo."
+                                    : "Deploy thread is initializing. It should appear automatically."}
+                                </div>
+                              }
+                            >
+                              <For each={session()?.messages ?? []}>
+                                {(message) => {
+                                  const invocations = messageInvocationResolver(message)
+                                  const style = ROLE_STREAM_STYLE[message.role]
+                                  return (
+                                    <div class="min-w-0 w-full px-2 md:px-6">
+                                      <div class="text-13-regular leading-relaxed whitespace-pre-wrap break-words">
+                                        <div class="flex items-center gap-1.5 mb-1">
+                                          <span class={`size-1.5 rounded-full shrink-0 ${style.dot}`} />
+                                          <span class={`text-10-medium uppercase tracking-wider ${style.label}`}>
+                                            {ROLE_LABEL[message.role]}
+                                          </span>
+                                          <span class="text-10-regular text-text-weak ml-auto">
+                                            {formatDate(message.createdAt)}
+                                          </span>
+                                        </div>
+                                        <div class={`${style.body} break-words`}>{message.text}</div>
+
+                                        <Show when={invocations.length > 0}>
+                                          <div class="mt-2.5 flex flex-col gap-2">
+                                            <For
+                                              each={invocations.filter(
+                                                (invocation) =>
+                                                  latestMessageByInvocation().get(invocation.id) === message.id,
+                                              )}
+                                            >
+                                              {(invocation) => (
+                                                <div class="rounded-xl border border-border-weak-base/70 bg-background-weak-base/20 p-2">
+                                                  <div class="mb-2 flex flex-wrap items-center justify-between gap-1.5">
+                                                    <span
+                                                      class={`inline-flex items-center gap-1.5 rounded-md border px-2 py-1 text-10-medium uppercase tracking-wide ${
+                                                        INVOCATION_STATUS_CLASS[invocation.status]
+                                                      }`}
+                                                    >
+                                                      <span>{TOOL_WIDGET_THEME[invocation.tool].label}</span>
+                                                      <span class="text-[9px] text-text-weak">
+                                                        {invocation.id.slice(-6)}
+                                                      </span>
                                                     </span>
-                                                  </span>
-                                                  <Button
-                                                    size="small"
-                                                    variant="ghost"
-                                                    class="h-6 px-2 text-[10px]"
-                                                    onClick={() => {
-                                                      setActiveInvocationId(invocation.id)
-                                                      setPaneDismissed(false)
-                                                    }}
-                                                  >
-                                                    Open Flight Deck
-                                                  </Button>
+                                                  </div>
+                                                  <InvocationWidget
+                                                    invocation={invocation}
+                                                    compact
+                                                    onOpenUrl={(url) => window.open(url, "_blank", "noopener,noreferrer")}
+                                                  />
                                                 </div>
-                                                <InvocationWidget
-                                                  invocation={invocation}
-                                                  compact
-                                                  onOpenUrl={(url) => window.open(url, "_blank", "noopener,noreferrer")}
-                                                />
-                                              </div>
-                                            )}
-                                          </For>
-                                        </div>
-                                      </Show>
+                                              )}
+                                            </For>
+                                          </div>
+                                        </Show>
+                                      </div>
                                     </div>
-                                  </div>
-                                )
-                              }}
-                            </For>
-                          </Show>
-
-                          <Show when={activeInvocation()}>
-                            {(invocation) => (
-                              <Show
-                                when={
-                                  invocation().status === "running" || !latestMessageByInvocation().has(invocation().id)
-                                }
-                              >
-                                <div class="mt-3 px-2 md:px-6">
-                                  <div class="rounded-xl border border-icon-warning-base/25 bg-icon-warning-base/8 p-2">
-                                    <div class="mb-2 flex items-center justify-between gap-2">
-                                      <span class="text-10-medium uppercase tracking-wider text-icon-warning-base">
-                                        Running Now
-                                      </span>
-                                      <Button
-                                        size="small"
-                                        variant="ghost"
-                                        class="h-6 px-2 text-[10px]"
-                                        onClick={() => {
-                                          setActiveInvocationId(invocation().id)
-                                          setPaneDismissed(false)
-                                        }}
-                                      >
-                                        Open Flight Deck
-                                      </Button>
+                                  )
+                                }}
+                              </For>
+                            </Show>
+
+                            <Show when={latestRunningInvocation()}>
+                              {(invocation) => (
+                                <Show
+                                  when={
+                                    invocation().status === "running" || !latestMessageByInvocation().has(invocation().id)
+                                  }
+                                >
+                                  <div class="mt-3 px-2 md:px-6">
+                                    <div class="rounded-xl border border-icon-warning-base/25 bg-icon-warning-base/8 p-2">
+                                      <div class="mb-2 flex items-center justify-between gap-2">
+                                        <span class="text-10-medium uppercase tracking-wider text-icon-warning-base">
+                                          Running Now
+                                        </span>
+                                      </div>
+                                      <InvocationWidget
+                                        invocation={invocation()}
+                                        compact
+                                        onOpenUrl={(url) => window.open(url, "_blank", "noopener,noreferrer")}
+                                      />
                                     </div>
-                                    <InvocationWidget
-                                      invocation={invocation()}
-                                      compact
-                                      onOpenUrl={(url) => window.open(url, "_blank", "noopener,noreferrer")}
-                                    />
                                   </div>
-                                </div>
-                              </Show>
-                            )}
+                                </Show>
+                              )}
+                            </Show>
                           </Show>
-                        </Show>
-                      </div>
-                    </div>
-                  </div>
-
-                  <div class="shrink-0 border-t border-border-weak-base bg-background-weak-base px-3 py-2.5">
-                    <form
-                      class="mx-auto flex w-full max-w-[1000px] flex-col gap-2 px-0 md:px-3"
-                      onSubmit={(event) => {
-                        event.preventDefault()
-                        if (!session() || !chatInput().trim() || sendingMessage()) return
-                        void sendMessage()
-                      }}
-                    >
-                      <div class="text-11-medium text-text-weak uppercase tracking-wider">Deploy Agent</div>
-                      <div class="flex items-end gap-2">
-                        <textarea
-                          class="flex-1 min-h-[44px] max-h-[110px] resize-y rounded-lg border border-border-weak-base bg-background-base px-2.5 py-2 text-12-regular text-text-strong focus:outline-none focus:border-border-base disabled:cursor-not-allowed disabled:opacity-60"
-                          value={chatInput()}
-                          onInput={(event) => setChatInput(event.currentTarget.value)}
-                          placeholder="Detect project type, run local deploy checks, capture evidence, and route failures to the linked run."
-                          disabled={!session() || sendingMessage()}
-                          onKeyDown={(event) => {
-                            if (event.key === "Enter" && !event.shiftKey) {
-                              event.preventDefault()
-                              if (!session() || !chatInput().trim() || sendingMessage()) return
-                              void sendMessage()
-                            }
-                          }}
-                        />
-                        <Button
-                          type="submit"
-                          size="small"
-                          variant="primary"
-                          class="h-8 px-2.5"
-                          disabled={!session() || !chatInput().trim() || sendingMessage()}
-                        >
-                          {sendingMessage() ? "Running..." : "Send"}
-                        </Button>
-                      </div>
-                      <div class="text-11-regular text-text-weak">Linked run: {session()?.linkedRunId ?? "none"}.</div>
-                    </form>
-                  </div>
-                </div>
-              </div>
-
-              <div
-                class={`h-full min-h-0 shrink-0 overflow-hidden transition-[width,transform,opacity] duration-400 ease-out ${
-                  toolPaneOpen() ? "translate-x-0 opacity-100" : "pointer-events-none translate-x-full opacity-0"
-                }`}
-                style={{
-                  width: toolPaneOpen() ? TOOL_PANE_WIDTH : "0px",
-                }}
-              >
-                <div
-                  class={`h-full min-h-0 bg-background-base ${toolPaneOpen() ? "border-l border-border-weak-base" : ""}`}
-                >
-                  <div class="flex h-full min-h-0 flex-col">
-                    <div class="border-b border-border-weak-base bg-background-weak-base px-4 py-3">
-                      <div class="flex items-start justify-between gap-2">
-                        <div>
-                          <div class="text-12-medium text-text-strong">Tool Flight Deck</div>
-                          <div class="mt-0.5 text-11-regular text-text-weak">
-                            Active tool details and live terminal output.
-                          </div>
-                          <div class="mt-1 text-[10px] text-text-weak">Configured tools: {tools().length}</div>
                         </div>
-                        <Button size="small" variant="ghost" class="h-7 px-2.5" onClick={() => setPaneDismissed(true)}>
-                          Close
-                        </Button>
                       </div>
                     </div>
 
-                    <div class="border-b border-border-weak-base/70 px-3 py-3">
-                      <div class="grid gap-2">
-                        <div class="flex flex-wrap gap-1.5">
-                          <input
-                            class="min-w-[180px] flex-1 rounded-md border border-border-weak-base bg-background-base px-2.5 py-1.5 text-11-regular text-text-base outline-none focus:border-border-base"
-                            value={runLinkInput()}
-                            onInput={(event) => setRunLinkInput(event.currentTarget.value)}
-                            placeholder="run-id for failure routing"
+                    <div class="shrink-0 border-t border-border-weak-base bg-background-weak-base px-3 py-2.5">
+                      <form
+                        class="mx-auto flex w-full max-w-[1000px] flex-col gap-2 px-0 md:px-3"
+                        onSubmit={(event) => {
+                          event.preventDefault()
+                          if (!session() || !chatInput().trim() || sendingMessage()) return
+                          void sendMessage()
+                        }}
+                      >
+                        <div class="text-11-medium text-text-weak uppercase tracking-wider">Deploy Agent</div>
+                        <div class="flex items-end gap-2">
+                          <textarea
+                            class="flex-1 min-h-[44px] max-h-[110px] resize-y rounded-lg border border-border-weak-base bg-background-base px-2.5 py-2 text-12-regular text-text-strong focus:outline-none focus:border-border-base disabled:cursor-not-allowed disabled:opacity-60"
+                            value={chatInput()}
+                            onInput={(event) => setChatInput(event.currentTarget.value)}
+                            placeholder="Detect project type, run local deploy checks, capture evidence, and route failures to the linked run."
+                            disabled={!session() || sendingMessage()}
+                            onKeyDown={(event) => {
+                              if (event.key === "Enter" && !event.shiftKey) {
+                                event.preventDefault()
+                                if (!session() || !chatInput().trim() || sendingMessage()) return
+                                void sendMessage()
+                              }
+                            }}
                           />
                           <Button
+                            type="submit"
                             size="small"
-                            variant="secondary"
-                            class="h-7 px-2.5"
-                            disabled={!session() || linkingRun()}
-                            onClick={() => {
-                              void linkRun(runLinkInput())
-                            }}
+                            variant="primary"
+                            class="h-8 px-2.5"
+                            disabled={!session() || !chatInput().trim() || sendingMessage()}
                           >
-                            {linkingRun() ? "Saving..." : "Link"}
+                            {sendingMessage() ? "Running..." : "Send"}
                           </Button>
+                        </div>
+                        <div class="text-11-regular text-text-weak">
+                          Linked run: {session()?.linkedRunId ?? "none"}.
+                        </div>
+                      </form>
+                    </div>
+                  </div>
+                </div>
+              }>
+                <Show
+                  when={surface()}
+                  fallback={
+                    <div class="flex min-h-0 flex-1 items-center justify-center bg-background-base px-6">
+                      <div class="max-w-xl rounded-xl border border-border-weak-base/80 bg-background-weak-base/30 p-4 text-center">
+                        <div class="text-12-medium text-text-strong">No runtime surface yet</div>
+                        <div class="mt-1 text-11-regular text-text-weak">
+                          Run deploy checks, then Open will bring up webview, interactive terminal, or external app.
+                        </div>
+                        <div class="mt-3">
                           <Button
                             size="small"
-                            variant="ghost"
+                            variant="secondary"
                             class="h-7 px-2.5"
-                            disabled={!session() || linkingRun() || !activeRunId()}
+                            disabled={openingApp()}
                             onClick={() => {
-                              const runId = activeRunId()
-                              setRunLinkInput(runId)
-                              void linkRun(runId)
+                              void openApp()
                             }}
                           >
-                            Active
+                            {openingApp() ? "Opening..." : "Open"}
                           </Button>
                         </div>
                       </div>
                     </div>
+                  }
+                >
+                  {(currentSurface) => (
+                    <div class="min-h-0 flex-1 bg-background-base">
+                      <Show when={currentSurface().kind === "web"}>
+                        <div class="h-full w-full">
+                          <iframe
+                            src={(currentSurface() as { kind: "web"; url: string }).url}
+                            class="h-full w-full border-0 bg-white"
+                            loading="eager"
+                            referrerPolicy="no-referrer"
+                            title="Deploy Runtime Webview"
+                          />
+                        </div>
+                      </Show>
 
-                    <div class="min-h-0 flex-1 overflow-auto p-3">
-                      <Show
-                        when={activeInvocation()}
-                        fallback={
-                          <div class="rounded-xl border border-border-weak-base/70 bg-background-weak-base/20 px-3 py-2 text-11-regular text-text-weak">
-                            No active tool yet. Ask the deploy agent in chat to run validation.
-                          </div>
-                        }
-                      >
-                        {(invocation) => (
-                          <div
-                            onMouseDown={() => {
-                              if (activeInvocationId() !== invocation().id) {
-                                setActiveInvocationId(invocation().id)
-                              }
-                            }}
-                          >
-                            <InvocationWidget
-                              invocation={invocation()}
-                              onOpenUrl={(url) => window.open(url, "_blank", "noopener,noreferrer")}
-                            />
+                      <Show when={currentSurface().kind === "terminal"}>
+                        <div class="h-full min-h-0">
+                          <Terminal pty={(currentSurface() as { kind: "terminal"; pty: LocalPTY }).pty} class="h-full min-h-0" />
+                        </div>
+                      </Show>
+
+                      <Show when={currentSurface().kind === "external"}>
+                        <div class="flex h-full items-center justify-center p-6">
+                          <div class="w-full max-w-2xl rounded-xl border border-border-weak-base/80 bg-background-weak-base/20 p-4">
+                            <div class="text-13-medium text-text-strong">External Runtime</div>
+                            <div class="mt-1 text-11-regular text-text-weak">
+                              Deploy launched an external target (for example Xcode, simulator, or desktop app).
+                            </div>
+                            <Show when={(currentSurface() as { kind: "external"; target?: DeployResolvedOpenTarget }).target}>
+                              {(target) => (
+                                <div class="mt-3 rounded-md border border-border-weak-base/80 bg-background-base/70 p-2 text-11-regular text-text-base break-all">
+                                  {target().type.toUpperCase()}: {target().target}
+                                </div>
+                              )}
+                            </Show>
+                            <Show when={externalOpenError()}>
+                              {(error) => (
+                                <div class="mt-3 rounded-md border border-icon-critical-base/30 bg-critical-tint-base/40 px-2 py-1.5 text-11-regular text-icon-critical-base">
+                                  {error()}
+                                </div>
+                              )}
+                            </Show>
+                            <div class="mt-3 flex flex-wrap gap-2">
+                              <Button
+                                size="small"
+                                variant="secondary"
+                                class="h-7 px-2.5"
+                                disabled={!deployOpenTarget()}
+                                onClick={() => {
+                                  const target = deployOpenTarget()
+                                  if (!target) return
+                                  setExternalOpenError(undefined)
+                                  void openDeployOpenTarget({ platform, target }).catch((error) => {
+                                    setExternalOpenError(error instanceof Error ? error.message : String(error))
+                                  })
+                                }}
+                              >
+                                Reopen External Target
+                              </Button>
+                              <Button
+                                size="small"
+                                variant="ghost"
+                                class="h-7 px-2.5"
+                                onClick={() => setViewMode("chat")}
+                              >
+                                Back To Chat
+                              </Button>
+                            </div>
                           </div>
-                        )}
+                        </div>
                       </Show>
                     </div>
-                  </div>
-                </div>
-              </div>
+                  )}
+                </Show>
+              </Show>
             </div>
           </div>
         </div>
diff --git a/packages/oneshot/src/deploy/session.ts b/packages/oneshot/src/deploy/session.ts
index 572a5b2..d282652 100644
--- a/packages/oneshot/src/deploy/session.ts
+++ b/packages/oneshot/src/deploy/session.ts
@@ -183,10 +183,18 @@ export const DeploySession = z.object({
   launchInstructions: DeployLaunchInstructions.optional(),
 })
 
+const DeployResolvedOpenTarget = z.object({
+  type: z.enum(["url", "path"]),
+  target: z.string(),
+  label: z.string().optional(),
+  app: z.string().optional(),
+})
+
 export const DeploySessionOpenResult = z.object({
   session: DeploySession,
   invocation: DeployToolInvocation,
   target: DeployOpenTarget,
+  openTarget: DeployResolvedOpenTarget.optional(),
   url: z.string().optional(),
   command: z.string().optional(),
   reused: z.boolean().default(false),
@@ -199,12 +207,7 @@ export type DeployArtifact = z.infer<typeof DeployArtifact>
 export type DeployMessage = z.infer<typeof DeployMessage>
 export type DeploySession = z.infer<typeof DeploySession>
 export type DeploySessionOpenResult = z.infer<typeof DeploySessionOpenResult>
-export type DeploySessionResolvedOpenTarget = {
-  type: "url" | "path"
-  target: string
-  label: string
-  app?: string
-}
+export type DeploySessionResolvedOpenTarget = z.infer<typeof DeployResolvedOpenTarget>
 
 type DeploySessionInternal = DeploySession & {
   activeExecution?: {
@@ -2284,6 +2287,44 @@ export function resolveDeploySessionOpenTarget(session: DeploySession): DeploySe
   }
 }
 
+function resolveOpenTargetForResult(input: {
+  session: DeploySessionInternal
+  target: z.infer<typeof DeployOpenTarget>
+  command?: string[]
+  url?: string
+}): DeploySessionResolvedOpenTarget | undefined {
+  const explicitUrl = input.url?.trim()
+  if (explicitUrl) {
+    return {
+      type: "url",
+      target: explicitUrl,
+      label: "Open App",
+    }
+  }
+
+  const pathLike = input.command
+    ?.map((part) => part.trim())
+    .find((part) => part.startsWith("/") || part.startsWith("./") || part.startsWith("../"))
+  if (pathLike && input.target === "external") {
+    return {
+      type: "path",
+      target: pathLike,
+      label: commandToString(input.command ?? []),
+    }
+  }
+
+  const fallback = resolveDeploySessionOpenTarget(input.session)
+  if (fallback) return fallback
+  if (input.target === "external") {
+    return {
+      type: "path",
+      target: input.session.directory,
+      label: "Open Workspace",
+    }
+  }
+  return undefined
+}
+
 function commandFromLaunchInvocation(invocation: DeployToolInvocation): string[] | undefined {
   if (invocation.tool === "terminal_exec") {
     const normalized = normalizeCommandInput(invocation.input?.command)
@@ -3484,9 +3525,37 @@ export async function openDeploySessionApp(input: {
       throw new Error("No launch command or preview URL is available for this deploy session yet.")
     }
 
+    const routeFailedOpenInvocation = async (failedInvocation: DeployToolInvocation): Promise<DeployToolInvocation> => {
+      const routed = await routeDeployFailuresToRun({
+        session,
+        failedInvocations: [failedInvocation],
+      })
+      if (!routed) return failedInvocation
+      const updated = updateInvocation(session, failedInvocation.id, {
+        routedToRun: {
+          runId: session.linkedRunId ?? "",
+          accepted: routed.accepted,
+          message: routed.message,
+          at: Date.now(),
+        },
+      })
+      pushMessage(session, {
+        role: "system",
+        text: routed.message,
+        invocationIds: [failedInvocation.id],
+      })
+      return updated ?? failedInvocation
+    }
+
     if (reusable && !input.forceRestart) {
       const reusablePty = Pty.get(reusable.ptyId)
       const reusedUrl = reusable.url || preferredUrl
+      const resolvedOpenTarget = resolveOpenTargetForResult({
+        session,
+        target: reusable.target,
+        command: reusable.command,
+        url: reusedUrl,
+      })
       if (reusedUrl) session.launchUrl = reusedUrl
       session.appStatus = "running"
       session.status = "passed"
@@ -3520,6 +3589,7 @@ export async function openDeploySessionApp(input: {
             livePtyId: reusable.ptyId,
             livePtyTitle: reusablePty?.title,
             keptRunning: true,
+            openTarget: resolvedOpenTarget,
           },
         },
       })
@@ -3536,6 +3606,7 @@ export async function openDeploySessionApp(input: {
         session: sanitizeSession(session),
         invocation: updated,
         target: reusable.target,
+        openTarget: resolvedOpenTarget,
         url: reusedUrl,
         command: commandToString(reusable.command),
         reused: true,
@@ -3560,6 +3631,11 @@ export async function openDeploySessionApp(input: {
 
     if (!command?.length) {
       const reachable = preferredUrl ? await probeUrl(preferredUrl) : false
+      const resolvedOpenTarget = resolveOpenTargetForResult({
+        session,
+        target,
+        url: preferredUrl,
+      })
       if (preferredUrl) session.launchUrl = preferredUrl
       session.appStatus = reachable ? "running" : "ready_for_manual_start"
       session.status = "passed"
@@ -3580,6 +3656,7 @@ export async function openDeploySessionApp(input: {
           meta: {
             openAction: true,
             reachable,
+            openTarget: resolvedOpenTarget,
           },
         },
       })
@@ -3594,6 +3671,7 @@ export async function openDeploySessionApp(input: {
         session: sanitizeSession(session),
         invocation: updated,
         target,
+        openTarget: resolvedOpenTarget,
         url: preferredUrl,
         reused: false,
         message: preferredUrl
@@ -3604,6 +3682,11 @@ export async function openDeploySessionApp(input: {
 
     const blocked = detectBlockedCommand(commandToString(command))
     if (blocked) {
+      const resolvedOpenTarget = resolveOpenTargetForResult({
+        session,
+        target,
+        command,
+      })
       session.status = "failed"
       session.lastError = blocked
       session.appStatus = "ready_for_manual_start"
@@ -3617,6 +3700,7 @@ export async function openDeploySessionApp(input: {
           code: 126,
           meta: {
             openAction: true,
+            openTarget: resolvedOpenTarget,
           },
         },
       })
@@ -3625,10 +3709,12 @@ export async function openDeploySessionApp(input: {
         text: `Open failed: ${blocked}`,
         invocationIds: [updated.id],
       })
+      const routedInvocation = await routeFailedOpenInvocation(updated)
       return {
         session: sanitizeSession(session),
-        invocation: updated,
+        invocation: routedInvocation,
         target,
+        openTarget: resolvedOpenTarget,
         command: commandToString(command),
         reused: false,
         message: blocked,
@@ -3697,6 +3783,11 @@ export async function openDeploySessionApp(input: {
       })
     } catch (error) {
       const message = error instanceof Error ? error.message : String(error)
+      const resolvedOpenTarget = resolveOpenTargetForResult({
+        session,
+        target,
+        command,
+      })
       session.status = "failed"
       session.lastError = message
       session.appStatus = "ready_for_manual_start"
@@ -3710,6 +3801,7 @@ export async function openDeploySessionApp(input: {
           command: commandToString(command),
           meta: {
             openAction: true,
+            openTarget: resolvedOpenTarget,
           },
         },
       })
@@ -3718,10 +3810,12 @@ export async function openDeploySessionApp(input: {
         text: `Open failed: ${message}`,
         invocationIds: [updated.id],
       })
+      const routedInvocation = await routeFailedOpenInvocation(updated)
       return {
         session: sanitizeSession(session),
-        invocation: updated,
+        invocation: routedInvocation,
         target,
+        openTarget: resolvedOpenTarget,
         command: commandToString(command),
         reused: false,
         message,
@@ -3796,6 +3890,12 @@ export async function openDeploySessionApp(input: {
           : detectedUrl
             ? `Launch command completed, and app is reachable at ${detectedUrl}.`
             : `Launch command completed: ${commandToString(command)}`
+    const resolvedOpenTarget = resolveOpenTargetForResult({
+      session,
+      target,
+      command,
+      url: detectedUrl,
+    })
 
     const updated = updateInvocationAndRequire(session, invocation, {
       status: session.status === "failed" ? "failed" : "passed",
@@ -3815,6 +3915,7 @@ export async function openDeploySessionApp(input: {
           livePtyId: ptyInfo.id,
           livePtyTitle: ptyInfo.title,
           livePtyCwd: ptyInfo.cwd,
+          openTarget: resolvedOpenTarget,
         },
       },
     })
@@ -3829,11 +3930,15 @@ export async function openDeploySessionApp(input: {
             : `Open started terminal ${ptyInfo.id}.`,
       invocationIds: [updated.id],
     })
+    const finalInvocation = session.status === "failed"
+      ? await routeFailedOpenInvocation(updated)
+      : updated
 
     return {
       session: sanitizeSession(session),
-      invocation: updated,
+      invocation: finalInvocation,
       target,
+      openTarget: resolvedOpenTarget,
       url: detectedUrl,
       command: commandToString(command),
       reused: false,
diff --git a/packages/oneshot/src/orchestrator/index.ts b/packages/oneshot/src/orchestrator/index.ts
index a4f9f24..295353a 100644
--- a/packages/oneshot/src/orchestrator/index.ts
+++ b/packages/oneshot/src/orchestrator/index.ts
@@ -49,6 +49,7 @@ import {
   setRunWorkflowID,
 } from "./runtime/store"
 import { collectLegacyDeployRemediationTaskFamily } from "./runtime/deploy-remediation"
+import { isRecoverableInfrastructureFault, summarizeRecoveryError } from "./runtime/recovery"
 
 export { Orchestrator } from "./types"
 
@@ -219,20 +220,49 @@ export async function startOrchestration(opts: {
       const currentGraph = currentRun ? getActiveGraph(currentRun.graphId) : undefined
       if (!currentRun || !currentGraph || currentRun.status !== "active") return
 
-      currentRun.status = "failed"
-      currentGraph.status = "failed"
-      currentRun.lastError = error instanceof Error ? error.message : String(error)
-      currentRun.pauseReason = undefined
-      currentRun.time.updated = Date.now()
-      currentRun.time.completed = Date.now()
-      currentGraph.time.completed = Date.now()
+      const now = Date.now()
+      const recoverable = isRecoverableInfrastructureFault(error)
+      if (recoverable) {
+        const summary = summarizeRecoveryError(error)
+        const message = `Run auto-paused for system recovery: ${summary}`
+        currentRun.status = "paused"
+        currentRun.lastError = message
+        currentRun.pauseReason = {
+          category: "system_recovery",
+          code: "workflow_start_retryable_failure",
+          message,
+          detectedAt: now,
+        }
+        currentRun.time.updated = now
+        currentRun.time.completed = undefined
+        if (currentGraph.status === "failed" || currentGraph.status === "killed" || currentGraph.status === "completed") {
+          currentGraph.status = "running"
+        }
+        currentGraph.time.completed = undefined
+      } else {
+        currentRun.status = "failed"
+        currentGraph.status = "failed"
+        currentRun.lastError = error instanceof Error ? error.message : String(error)
+        currentRun.pauseReason = undefined
+        currentRun.time.updated = now
+        currentRun.time.completed = now
+        currentGraph.time.completed = now
+      }
       emitRunUpdated(currentRun)
       await saveRunSnapshot(projectRoot, currentRun, currentGraph).catch(() => {})
-      log.error("Failed to start orchestration workflow", {
-        runId,
-        error: error instanceof Error ? error.message : String(error),
-        errorRaw: typeof error === "object" && error !== null ? error : undefined,
-      })
+      if (recoverable) {
+        log.warn("Recoverable failure while starting orchestration workflow; run paused for recovery", {
+          runId,
+          error: error instanceof Error ? error.message : String(error),
+          errorRaw: typeof error === "object" && error !== null ? error : undefined,
+        })
+      } else {
+        log.error("Failed to start orchestration workflow", {
+          runId,
+          error: error instanceof Error ? error.message : String(error),
+          errorRaw: typeof error === "object" && error !== null ? error : undefined,
+        })
+      }
     }
   })()
 
@@ -618,20 +648,45 @@ export async function resumeFromSnapshot(
     })
     setRunWorkflowID(run.id, workflowId)
   } catch (error) {
-    run.status = "failed"
-    run.lastError = error instanceof Error ? error.message : String(error)
-    run.pauseReason = undefined
-    run.time.updated = Date.now()
-    run.time.completed = Date.now()
-    graph.status = "failed"
-    graph.time.completed = Date.now()
+    const now = Date.now()
+    const recoverable = isRecoverableInfrastructureFault(error)
+    if (recoverable) {
+      const summary = summarizeRecoveryError(error)
+      const message = `Run auto-paused for system recovery: ${summary}`
+      run.status = "paused"
+      run.lastError = message
+      run.pauseReason = {
+        category: "system_recovery",
+        code: "workflow_resume_retryable_failure",
+        message,
+        detectedAt: now,
+      }
+      run.time.updated = now
+      run.time.completed = undefined
+      graph.time.completed = undefined
+    } else {
+      run.status = "failed"
+      run.lastError = error instanceof Error ? error.message : String(error)
+      run.pauseReason = undefined
+      run.time.updated = now
+      run.time.completed = now
+      graph.status = "failed"
+      graph.time.completed = now
+    }
     emitRunUpdated(run)
     await saveRunSnapshot(runProjectRoot, run, graph).catch(() => {})
 
-    log.error("Failed to resume orchestration workflow", {
-      runId: run.id,
-      error: error instanceof Error ? error.message : String(error),
-    })
+    if (recoverable) {
+      log.warn("Recoverable failure while resuming orchestration workflow; run paused for recovery", {
+        runId: run.id,
+        error: error instanceof Error ? error.message : String(error),
+      })
+    } else {
+      log.error("Failed to resume orchestration workflow", {
+        runId: run.id,
+        error: error instanceof Error ? error.message : String(error),
+      })
+    }
     return run
   }
 
diff --git a/packages/oneshot/src/orchestrator/runtime/langgraph-engine.ts b/packages/oneshot/src/orchestrator/runtime/langgraph-engine.ts
index f036c37..657bcba 100644
--- a/packages/oneshot/src/orchestrator/runtime/langgraph-engine.ts
+++ b/packages/oneshot/src/orchestrator/runtime/langgraph-engine.ts
@@ -1459,7 +1459,66 @@ function shouldExpandChecklistIntoSubtasks(input: {
     || corpus.includes("launch")
 
   if (!remediationLike) return false
-  return extractNumberedChecklistSteps(task.description).length >= 4
+  const numberedSteps = extractNumberedChecklistSteps(task.description)
+  if (numberedSteps.length < 4) return false
+  const coalescedSteps = coalesceChecklistSteps(numberedSteps)
+  // Avoid converting a remediation task into orchestration when checklist
+  // expansion would still produce only one or two micro-steps.
+  return coalescedSteps.length >= 3
+}
+
+function isCommandLikeChecklistStep(step: string): boolean {
+  const normalized = step
+    .trim()
+    .toLowerCase()
+    .replace(/^[-*]\s+/, "")
+    .replace(/`+/g, "")
+  if (!normalized) return false
+
+  const strippedLeadVerb = normalized.replace(/^(run|execute)\s+/, "")
+  if (
+    /^(npm|pnpm|yarn|bun|npx|node|tsx|ts-node|tsc|prisma|python|pip|poetry|cargo|go|make|cmake|gradle|mvn|docker|git)\b/
+      .test(strippedLeadVerb)
+  ) {
+    return true
+  }
+
+  const hasTool = /\b(npm|pnpm|yarn|bun|npx|prisma|tsc|tsx|next build|next dev|next lint)\b/.test(normalized)
+  const hasExecutionVerb = /\b(run|command|install|execute|invoke|generate|push|migrate|seed|build|start)\b/.test(normalized)
+  return hasTool && hasExecutionVerb
+}
+
+function coalesceChecklistSteps(steps: string[]): string[] {
+  const coalesced: string[] = []
+  let commandSequence: string[] = []
+
+  const flushCommandSequence = (): void => {
+    if (commandSequence.length === 0) return
+    if (commandSequence.length === 1) {
+      coalesced.push(commandSequence[0])
+      commandSequence = []
+      return
+    }
+    coalesced.push(
+      [
+        "Run command sequence:",
+        ...commandSequence.map((step, index) => `${index + 1}. ${step}`),
+      ].join("\n"),
+    )
+    commandSequence = []
+  }
+
+  for (const step of steps) {
+    if (isCommandLikeChecklistStep(step)) {
+      commandSequence.push(step)
+      continue
+    }
+    flushCommandSequence()
+    coalesced.push(step)
+  }
+  flushCommandSequence()
+
+  return coalesced
 }
 
 function expandChecklistIntoSubtasks(input: {
@@ -1470,8 +1529,8 @@ function expandChecklistIntoSubtasks(input: {
 }): string[] {
   const { graph, task, now, existingIds } = input
   const originalKind = task.kind
-  const steps = extractNumberedChecklistSteps(task.description)
-  if (steps.length < 4) return []
+  const steps = coalesceChecklistSteps(extractNumberedChecklistSteps(task.description))
+  if (steps.length < 3) return []
 
   const metadata = ensureTaskMetadataObject(task)
   if (metadata._checklistExpanded === true) return []
@@ -2346,6 +2405,42 @@ async function supervisorNode(state: EngineState): Promise<Partial<EngineState>>
     return {}
   }
 
+  const convergenceGuard = constrainReplanDecisionForConvergence({
+    graph,
+    decision,
+    failedTasks: replanningFailedTasks,
+    failedGates,
+    remainingTokens: budgetState.remainingToKill,
+    averageTokensPerTask: averages.averageTokensPerTask,
+  })
+  decision = convergenceGuard.decision
+  if (convergenceGuard.notes.length > 0) {
+    const convergenceNote = convergenceGuard.notes.join(" ")
+    decision.reasoning = `${decision.reasoning}\n${convergenceNote}`
+    log.info("Supervisor convergence guard adjusted replan decision", {
+      runId: run.id,
+      mode: convergenceGuard.snapshot.mode,
+      unresolvedQueue: convergenceGuard.snapshot.unresolvedTasks,
+      targetUnresolved: convergenceGuard.snapshot.targetUnresolved,
+      tasksToAdd: decision.tasksToAdd.length,
+      tasksToRetry: decision.tasksToRetry.length,
+      tasksToSkip: decision.tasksToSkip.length,
+      note: convergenceNote,
+    })
+  }
+
+  if (
+    decision.tasksToAdd.length === 0
+    && decision.tasksToRetry.length === 0
+    && decision.tasksToSkip.length === 0
+  ) {
+    emitSupervisorThought(run.id, {
+      reasoning: "Supervisor replan became non-actionable after convergence guard checks.",
+      action: "accept",
+    })
+    return {}
+  }
+
   if (BUDGET_GOVERNOR_ENABLED && decision.tasksToAdd.length > maxAffordableTasksToAdd) {
     decision.tasksToAdd = decision.tasksToAdd.slice(0, Math.max(0, maxAffordableTasksToAdd))
     decision.reasoning = `${decision.reasoning}\nTask additions capped to ${maxAffordableTasksToAdd} due to token headroom constraints.`
@@ -3337,6 +3432,224 @@ function readVerificationFailureFeedbackEntries(value: unknown): VerificationFai
 // PHASE 1: Supervisor replan decision
 // ═══════════════════════════════════════════════════════════════════════════════
 
+type ReplanConvergenceMode = "expand" | "stabilize" | "converge"
+
+type ReplanConvergenceSnapshot = {
+  mode: ReplanConvergenceMode
+  unresolvedTasks: number
+  totalTasks: number
+  queuePressure: number
+  targetUnresolved: number
+  maxProjectedUnresolved: number
+  lowHeadroom: boolean
+  lowHeadroomThreshold: number
+}
+
+function buildReplanConvergenceSnapshot(input: {
+  graph: Orchestrator.TaskGraph
+  failedTasks: Orchestrator.Task[]
+  failedGates: Orchestrator.Task[]
+  remainingTokens: number
+  averageTokensPerTask: number
+}): ReplanConvergenceSnapshot {
+  const tasks = Object.values(input.graph.tasks)
+  const totalTasks = tasks.length
+  const unresolvedTasks = tasks.filter((task) => task.status === "pending" || task.status === "in_progress").length
+  const queuePressure = unresolvedTasks / Math.max(1, totalTasks)
+  const targetUnresolved = Math.max(8, Math.ceil(Math.sqrt(Math.max(1, totalTasks)) * 2.25))
+
+  const lowHeadroomThreshold = Math.max(
+    80_000,
+    Math.round(Math.max(1, input.averageTokensPerTask) * 1.5),
+  )
+  const lowHeadroom = input.remainingTokens <= lowHeadroomThreshold
+  const highReplanPressure = input.graph.replanCount >= 3
+  const backlogPressure = unresolvedTasks > targetUnresolved
+  const failureSignals = input.failedTasks.length + input.failedGates.length
+  const mode: ReplanConvergenceMode = lowHeadroom || (highReplanPressure && backlogPressure)
+    ? "converge"
+    : (backlogPressure || highReplanPressure || failureSignals >= 2)
+      ? "stabilize"
+      : "expand"
+
+  const growthAllowance = mode === "converge"
+    ? Math.max(0, Math.ceil(failureSignals / 3))
+    : mode === "stabilize"
+      ? Math.max(1, Math.ceil(failureSignals / 2))
+      : Math.max(2, Math.ceil(failureSignals / 2))
+
+  return {
+    mode,
+    unresolvedTasks,
+    totalTasks,
+    queuePressure,
+    targetUnresolved,
+    maxProjectedUnresolved: Math.max(targetUnresolved, unresolvedTasks + growthAllowance),
+    lowHeadroom,
+    lowHeadroomThreshold,
+  }
+}
+
+function buildReplanAnchorTaskIDs(input: {
+  graph: Orchestrator.TaskGraph
+  failedTasks: Orchestrator.Task[]
+  failedGates: Orchestrator.Task[]
+  decision: Orchestrator.ReplanDecision
+}): Set<string> {
+  const anchors = new Set<string>()
+  const rememberTask = (task: Orchestrator.Task | undefined): void => {
+    if (!task) return
+    anchors.add(task.id)
+    if (task.parentTaskId) anchors.add(task.parentTaskId)
+  }
+
+  for (const failedTask of input.failedTasks) rememberTask(failedTask)
+  for (const failedGate of input.failedGates) rememberTask(failedGate)
+
+  for (const retry of input.decision.tasksToRetry) {
+    const task = input.graph.tasks[retry.taskId]
+    rememberTask(task)
+  }
+
+  for (const task of Object.values(input.graph.tasks)) {
+    if (!isSubOrchestratorTask(task)) continue
+    if (task.status !== "in_progress" && task.status !== "failed" && task.status !== "blocked") continue
+    rememberTask(task)
+  }
+
+  return anchors
+}
+
+function scoreReplanTaskAdditionAnchor(input: {
+  graph: Orchestrator.TaskGraph
+  task: Orchestrator.ReplanDecision["tasksToAdd"][number]
+  anchorIDs: Set<string>
+}): number {
+  if (input.anchorIDs.size === 0) return 1
+
+  let score = 0
+  if (input.task.parentTaskId && input.anchorIDs.has(input.task.parentTaskId)) score += 6
+  if ((input.task.dependencies ?? []).some((depID) => input.anchorIDs.has(depID))) score += 4
+
+  const corpus = [
+    input.task.id,
+    input.task.name,
+    input.task.description,
+    ...(input.task.files ?? []),
+    ...(input.task.acceptanceCriteria ?? []),
+  ].join(" ")
+  for (const anchorID of input.anchorIDs) {
+    const anchorTask = input.graph.tasks[anchorID]
+    if (!anchorTask) continue
+    if (!replanCorpusLikelyTargetsTask(corpus, anchorTask)) continue
+    score += 3
+    break
+  }
+
+  if (input.task.kind === "orchestration") score += 1
+  if (input.task.kind === "validation" || input.task.kind === "remediation") score -= 1
+  return score
+}
+
+function constrainReplanDecisionForConvergence(input: {
+  graph: Orchestrator.TaskGraph
+  decision: Orchestrator.ReplanDecision
+  failedTasks: Orchestrator.Task[]
+  failedGates: Orchestrator.Task[]
+  remainingTokens: number
+  averageTokensPerTask: number
+}): {
+  decision: Orchestrator.ReplanDecision
+  notes: string[]
+  snapshot: ReplanConvergenceSnapshot
+} {
+  const snapshot = buildReplanConvergenceSnapshot({
+    graph: input.graph,
+    failedTasks: input.failedTasks,
+    failedGates: input.failedGates,
+    remainingTokens: input.remainingTokens,
+    averageTokensPerTask: input.averageTokensPerTask,
+  })
+  const notes: string[] = []
+
+  if (snapshot.mode === "expand" || input.decision.tasksToAdd.length === 0) {
+    return {
+      decision: input.decision,
+      notes,
+      snapshot,
+    }
+  }
+
+  const anchorIDs = buildReplanAnchorTaskIDs({
+    graph: input.graph,
+    failedTasks: input.failedTasks,
+    failedGates: input.failedGates,
+    decision: input.decision,
+  })
+  const rankedAdditions = input.decision.tasksToAdd
+    .map((task, index) => ({
+      task,
+      index,
+      score: scoreReplanTaskAdditionAnchor({
+        graph: input.graph,
+        task,
+        anchorIDs,
+      }),
+    }))
+    .sort((left, right) => right.score - left.score || left.index - right.index)
+
+  let candidateAdditions = rankedAdditions
+  if (snapshot.mode === "converge" && anchorIDs.size > 0) {
+    const anchoredOnly = rankedAdditions.filter((candidate) => candidate.score > 0)
+    if (anchoredOnly.length < rankedAdditions.length) {
+      notes.push(
+        `Convergence mode pruned ${rankedAdditions.length - anchoredOnly.length} unanchored task addition(s).`,
+      )
+      candidateAdditions = anchoredOnly
+    }
+  }
+
+  const unresolvedSkipCount = input.decision.tasksToSkip
+    .map((taskID) => input.graph.tasks[taskID]?.status)
+    .filter((status) => status === "pending" || status === "in_progress")
+    .length
+  const unresolvedRetryCount = input.decision.tasksToRetry
+    .map((retry) => input.graph.tasks[retry.taskId]?.status)
+    .filter((status) => status === "failed" || status === "blocked" || status === "skipped")
+    .length
+  const projectedUnresolved =
+    snapshot.unresolvedTasks
+    - unresolvedSkipCount
+    + unresolvedRetryCount
+    + candidateAdditions.length
+
+  if (projectedUnresolved > snapshot.maxProjectedUnresolved && candidateAdditions.length > 0) {
+    const overshoot = projectedUnresolved - snapshot.maxProjectedUnresolved
+    const keepCount = Math.max(0, candidateAdditions.length - overshoot)
+    const trimmed = candidateAdditions.slice(0, keepCount)
+    if (trimmed.length < candidateAdditions.length) {
+      notes.push(
+        `Queue-pressure guard trimmed task additions from ${candidateAdditions.length} to ${trimmed.length} `
+        + `(target unresolved ≤ ${snapshot.maxProjectedUnresolved}).`,
+      )
+      candidateAdditions = trimmed
+    }
+  }
+
+  const nextTasksToAdd = candidateAdditions
+    .sort((left, right) => left.index - right.index)
+    .map((candidate) => candidate.task)
+
+  return {
+    decision: {
+      ...input.decision,
+      tasksToAdd: nextTasksToAdd,
+    },
+    notes,
+    snapshot,
+  }
+}
+
 async function buildReplanDecision(input: {
   rootPrompt: string
   providerID: string
@@ -3388,6 +3701,14 @@ async function buildReplanDecision(input: {
     .join("\n")
     .slice(0, MAX_SCRATCHPAD_CONTEXT_CHARS)
 
+  const convergenceSnapshot = buildReplanConvergenceSnapshot({
+    graph: input.graph,
+    failedTasks: input.failedTasks,
+    failedGates: input.failedGates,
+    remainingTokens: input.remainingTokens,
+    averageTokensPerTask: input.averageTokensPerTask,
+  })
+
   try {
     return await generateStructuredObjectWithFallback({
       model,
@@ -3431,6 +3752,14 @@ Token budget:
 - Observed average tokens per completed task: ${Math.round(input.averageTokensPerTask).toLocaleString()}
 - Maximum affordable tasksToAdd this cycle: ${input.maxAffordableTasksToAdd}
 
+Convergence state:
+- Mode: ${convergenceSnapshot.mode}
+- Unresolved queue (pending+in_progress): ${convergenceSnapshot.unresolvedTasks}/${convergenceSnapshot.totalTasks}
+- Queue pressure ratio: ${convergenceSnapshot.queuePressure.toFixed(2)}
+- Target unresolved queue: ${convergenceSnapshot.targetUnresolved}
+- Low-headroom threshold: ${convergenceSnapshot.lowHeadroomThreshold.toLocaleString()} (active=${convergenceSnapshot.lowHeadroom ? "yes" : "no"})
+- Projected unresolved queue should stay <= ${convergenceSnapshot.maxProjectedUnresolved}
+
 Current task states:
 ${JSON.stringify(taskSummary, null, 2)}
 
@@ -3454,7 +3783,11 @@ ${scratchpadContext || "(empty)"}
 
 Replan cycle: ${input.graph.replanCount + 1} of ${input.graph.maxReplanCycles}
 
-Decide: should we replan? If so, what tasks to add, retry, or skip?`,
+Decide: should we replan? If so, what tasks to add, retry, or skip?
+When convergence mode is "stabilize" or "converge", avoid broad top-level task growth:
+- Prefer retries and targeted skips first.
+- Add tasks only when they are anchored to specific failed tasks/sub-orchestrators (use parentTaskId).
+- Do not increase unresolved backlog unless absolutely required for recovery.`,
     })
   } catch (error) {
     const message = errorMessage(error)
@@ -4201,6 +4534,12 @@ function assertRunStillActive(runId: string, phase: string): void {
   }
 }
 
+function normalizeTaskSessionTitle(taskName: string): string {
+  const trimmed = taskName.trim()
+  const withoutLegacyPrefix = trimmed.replace(/^oneshot task:\s*/i, "")
+  return withoutLegacyPrefix.trim() || "Task"
+}
+
 async function runTaskPromptInDirectory(input: {
   run: Orchestrator.Run
   task: Orchestrator.Task
@@ -4239,7 +4578,7 @@ async function runTaskPromptInDirectory(input: {
             ? await Session.get(candidateSessionId).catch(() => undefined)
             : undefined
           const session = existingSession ?? await Session.create({
-            title: `OneShot Task: ${input.task.name}`,
+            title: normalizeTaskSessionTitle(input.task.name),
           })
 
           clearTaskRetryMode(input.task)
@@ -4889,9 +5228,9 @@ async function executeSubOrchestrator(state: EngineState, task: Orchestrator.Tas
     totalOutput += subtask.tokenUsage?.outputTokens ?? 0
   }
   task.tokenUsage = { inputTokens: totalInput, outputTokens: totalOutput }
-  run.globalTokenUsage.inputTokens += totalInput
-  run.globalTokenUsage.outputTokens += totalOutput
-  run.globalTokenUsage.totalTokens += totalInput + totalOutput
+  // Child tasks already account for token usage when they complete.
+  // Keep parent tokenUsage as an aggregate for reporting, but do not
+  // re-add those child tokens to the global run counters.
 
   if (run.status !== "active" || unresolvedSubs.length > 0 || (failedSubs.length > 0 && completedSubs.length < subResults.length / 2)) {
     task.status = "failed"
@@ -6499,6 +6838,28 @@ export const ReplanDecisionInternals = {
   sanitizeReplanDecision: sanitizeReplanDecisionForTesting,
   hasLiveDependentTask,
   replanCorpusLikelyTargetsTask,
+  constrainReplanDecisionForConvergence(
+    input: {
+      graph: Orchestrator.TaskGraph
+      decision: Orchestrator.ReplanDecision
+      failedTasks: Orchestrator.Task[]
+      failedGates: Orchestrator.Task[]
+      remainingTokens: number
+      averageTokensPerTask: number
+    },
+  ): Orchestrator.ReplanDecision {
+    return constrainReplanDecisionForConvergence(input).decision
+  },
+  buildReplanConvergenceSnapshot,
+}
+
+export const ChecklistExpansionInternals = {
+  isCommandLikeChecklistStepForTesting(step: string): boolean {
+    return isCommandLikeChecklistStep(step)
+  },
+  coalesceChecklistStepsForTesting(steps: string[]): string[] {
+    return coalesceChecklistSteps(steps)
+  },
 }
 
 export const PlanningInternals = {
diff --git a/packages/oneshot/src/orchestrator/runtime/recovery.ts b/packages/oneshot/src/orchestrator/runtime/recovery.ts
new file mode 100644
index 0000000..d6eb5a3
--- /dev/null
+++ b/packages/oneshot/src/orchestrator/runtime/recovery.ts
@@ -0,0 +1,105 @@
+const TRANSIENT_INFRA_PATTERNS: RegExp[] = [
+  /\beagain\b/i,
+  /\bemfile\b/i,
+  /\benfile\b/i,
+  /\beai_again\b/i,
+  /resource temporarily unavailable/i,
+  /too many open files/i,
+  /posix_spawn/i,
+  /spawn\s+['"`]?[^'"`\s]+['"`]?/i,
+  /\betimedout\b/i,
+  /\beconnreset\b/i,
+  /\beconnrefused\b/i,
+  /\benet(unreach|down)\b/i,
+  /network (?:is )?unreachable/i,
+  /connection (?:reset|closed|refused|timed out)/i,
+  /service unavailable/i,
+  /temporar(?:y|ily) unavailable/i,
+]
+
+const GENERIC_ACTIVITY_FAILURE_PATTERNS: RegExp[] = [
+  /activity task failed/i,
+  /workflow task failed/i,
+]
+
+function normalizeMessage(value: string): string {
+  return value.replace(/\s+/g, " ").trim()
+}
+
+function pushMessage(target: string[], value: unknown): void {
+  if (typeof value !== "string") return
+  const normalized = normalizeMessage(value)
+  if (!normalized) return
+  target.push(normalized)
+}
+
+export function collectErrorMessages(error: unknown, maxDepth = 6): string[] {
+  const output: string[] = []
+  const visited = new Set<object>()
+
+  const walk = (value: unknown, depth: number): void => {
+    if (value == null || depth > maxDepth) return
+    if (typeof value === "string") {
+      pushMessage(output, value)
+      return
+    }
+    if (typeof value === "number" || typeof value === "boolean") {
+      pushMessage(output, String(value))
+      return
+    }
+    if (typeof value !== "object") return
+
+    if (visited.has(value)) return
+    visited.add(value)
+
+    if (Array.isArray(value)) {
+      for (const item of value.slice(0, 12)) walk(item, depth + 1)
+      return
+    }
+
+    const record = value as Record<string, unknown>
+    pushMessage(output, record.name)
+    pushMessage(output, record.type)
+    pushMessage(output, record.code)
+    pushMessage(output, record.message)
+    pushMessage(output, record.reason)
+    pushMessage(output, record.details)
+    pushMessage(output, record.stack)
+
+    walk(record.cause, depth + 1)
+    walk(record.failure, depth + 1)
+    walk(record.error, depth + 1)
+    walk(record.innerError, depth + 1)
+    walk(record.errors, depth + 1)
+  }
+
+  walk(error, 0)
+
+  const unique = new Set<string>()
+  for (const message of output) unique.add(message)
+  return [...unique]
+}
+
+export function summarizeRecoveryError(error: unknown): string {
+  const messages = collectErrorMessages(error)
+  if (messages.length === 0) return "Transient orchestration runtime fault"
+
+  const preferred = messages.find((message) => !GENERIC_ACTIVITY_FAILURE_PATTERNS.some((pattern) => pattern.test(message)))
+  const picked = preferred ?? messages[0]
+  if (picked.length <= 220) return picked
+  return `${picked.slice(0, 217)}...`
+}
+
+export function isRecoverableInfrastructureFault(error: unknown): boolean {
+  const messages = collectErrorMessages(error)
+  if (messages.length === 0) return false
+  const corpus = messages.join("\n")
+
+  if (TRANSIENT_INFRA_PATTERNS.some((pattern) => pattern.test(corpus))) return true
+
+  // Preserve run continuity by defaulting unknown activity/workflow task failures
+  // into system-recovery pause/resume rather than hard-failing the run.
+  if (GENERIC_ACTIVITY_FAILURE_PATTERNS.some((pattern) => pattern.test(corpus))) return true
+
+  return false
+}
diff --git a/packages/oneshot/src/orchestrator/runtime/verification.ts b/packages/oneshot/src/orchestrator/runtime/verification.ts
index 0fc0982..e11616c 100644
--- a/packages/oneshot/src/orchestrator/runtime/verification.ts
+++ b/packages/oneshot/src/orchestrator/runtime/verification.ts
@@ -1,4 +1,5 @@
 import path from "node:path"
+import { existsSync } from "node:fs"
 import { mkdtemp, readFile, rm, stat } from "node:fs/promises"
 import { tmpdir } from "node:os"
 import { Orchestrator } from "../types"
@@ -7,6 +8,21 @@ import { hydrateWorktreeDependencies } from "./dependency-bootstrap"
 const DEFAULT_COMMAND_TIMEOUT_MS = Number(process.env.ONESHOT_VERIFICATION_COMMAND_TIMEOUT_MS ?? 120_000)
 const MAX_OUTPUT_SAMPLE_CHARS = Number(process.env.ONESHOT_VERIFICATION_OUTPUT_CHARS ?? 2_000)
 const TSC_SHIM_SENTINEL_RE = /this is not the tsc command you are looking for/i
+const VERIFICATION_PATH_REBASE_ANCHORS = new Set([
+  "app",
+  "apps",
+  "backend",
+  "docs",
+  "frontend",
+  "lib",
+  "libs",
+  "packages",
+  "scripts",
+  "services",
+  "src",
+  "test",
+  "tests",
+])
 const VERIFICATION_ISOLATE_WORKTREE = parseBooleanEnv(
   process.env.ONESHOT_VERIFICATION_ISOLATE_WORKTREE,
   true,
@@ -515,13 +531,111 @@ function resolveVerificationPath(
   rawPath: string,
 ): { ok: true; absolutePath: string } | { ok: false; error: string } {
   const projectRootResolved = path.resolve(projectRoot)
-  const absolutePath = path.resolve(projectRootResolved, rawPath)
+  const absolutePath = resolveVerificationAbsolutePath(projectRootResolved, rawPath)
   if (!isPathInsideRoot(projectRootResolved, absolutePath)) {
     return { ok: false, error: "Verification path resolves outside project root" }
   }
   return { ok: true, absolutePath }
 }
 
+function resolveVerificationAbsolutePath(projectRootResolved: string, rawPath: string): string {
+  const trimmed = rawPath.trim()
+  if (!trimmed) return path.resolve(projectRootResolved, trimmed)
+
+  // Most checks are project-relative; keep the fast path first.
+  if (!path.isAbsolute(trimmed)) {
+    return path.resolve(projectRootResolved, trimmed)
+  }
+
+  const absolutePath = path.resolve(trimmed)
+  const rebased = rebaseAbsoluteVerificationPath(projectRootResolved, absolutePath)
+  if (rebased) return path.resolve(projectRootResolved, rebased)
+
+  if (isPathInsideRoot(projectRootResolved, absolutePath)) return absolutePath
+
+  return absolutePath
+}
+
+function rebaseAbsoluteVerificationPath(projectRootResolved: string, absolutePath: string): string | undefined {
+  const normalized = absolutePath.replace(/\\/g, "/")
+  const candidates: string[] = []
+
+  // Common worker layout:
+  // .../.oneshot/worktrees/<run-id>/<task-worktree>/<project-relative-path>
+  const oneShotMarker = "/.oneshot/worktrees/"
+  const oneShotIndex = normalized.indexOf(oneShotMarker)
+  if (oneShotIndex >= 0) {
+    const tailSegments = normalized
+      .slice(oneShotIndex + oneShotMarker.length)
+      .split("/")
+      .filter(Boolean)
+    if (tailSegments.length > 2) {
+      candidates.push(tailSegments.slice(2).join("/"))
+    }
+  }
+
+  // Generic worktree fallback:
+  // .../worktrees/<name>/<project-relative-path>
+  const genericMarker = "/worktrees/"
+  const genericIndex = normalized.lastIndexOf(genericMarker)
+  if (genericIndex >= 0) {
+    const tailSegments = normalized
+      .slice(genericIndex + genericMarker.length)
+      .split("/")
+      .filter(Boolean)
+    if (tailSegments.length > 1) {
+      candidates.push(tailSegments.slice(1).join("/"))
+    }
+  }
+
+  const segments = normalized.split("/").filter(Boolean)
+
+  // Anchor on common repository roots (src/, packages/, frontend/, etc.).
+  for (let index = 0; index < segments.length; index += 1) {
+    if (!VERIFICATION_PATH_REBASE_ANCHORS.has(segments[index].toLowerCase())) continue
+    candidates.push(segments.slice(index).join("/"))
+  }
+
+  // Last-resort suffix search.
+  for (let length = Math.min(8, segments.length); length >= 2; length -= 1) {
+    candidates.push(segments.slice(segments.length - length).join("/"))
+  }
+
+  return pickBestRebasedCandidate(projectRootResolved, candidates)
+}
+
+function pickBestRebasedCandidate(projectRootResolved: string, candidates: string[]): string | undefined {
+  const seen = new Set<string>()
+  const normalizedCandidates: string[] = []
+
+  for (const candidate of candidates) {
+    const cleaned = candidate
+      .replace(/^\/+/, "")
+      .replace(/\/+/g, "/")
+      .trim()
+    if (!cleaned || cleaned === "." || cleaned === "..") continue
+    if (seen.has(cleaned)) continue
+    seen.add(cleaned)
+    normalizedCandidates.push(cleaned)
+  }
+
+  // Prefer candidates that start with a path segment that exists in the target project.
+  for (const cleaned of normalizedCandidates) {
+    const resolved = path.resolve(projectRootResolved, cleaned)
+    if (!isPathInsideRoot(projectRootResolved, resolved)) continue
+    const firstSegment = cleaned.split("/").find(Boolean)
+    if (!firstSegment) continue
+    if (existsSync(path.join(projectRootResolved, firstSegment))) return cleaned
+  }
+
+  for (const cleaned of normalizedCandidates) {
+    const resolved = path.resolve(projectRootResolved, cleaned)
+    if (isPathInsideRoot(projectRootResolved, resolved)) return cleaned
+  }
+
+  return undefined
+}
+
 function isPathInsideRoot(projectRoot: string, absolutePath: string): boolean {
   const root = normalizeForPathCompare(projectRoot)
   const target = normalizeForPathCompare(absolutePath)
diff --git a/packages/oneshot/src/orchestrator/runtime/workflow.ts b/packages/oneshot/src/orchestrator/runtime/workflow.ts
index 2f26aee..f22f27d 100644
--- a/packages/oneshot/src/orchestrator/runtime/workflow.ts
+++ b/packages/oneshot/src/orchestrator/runtime/workflow.ts
@@ -15,6 +15,7 @@ import {
   type RunModelMap,
   type RunModelOverrides,
 } from "../model-config"
+import { isRecoverableInfrastructureFault, summarizeRecoveryError } from "./recovery"
 
 export interface OrchestrationWorkflowInput {
   runId: string
@@ -105,6 +106,18 @@ const DEADLOCK_SUPERVISOR_THRESHOLD = 3
 const DEADLOCK_FAIL_THRESHOLD = 8
 const DEADLOCK_FAIL_THRESHOLD_WITH_FAILURES = 24
 const ACTIVITY_HEARTBEAT_TIMEOUT = "30s"
+const ORCHESTRATION_ACTIVITY_RETRY = {
+  initialInterval: "1s",
+  backoffCoefficient: 2,
+  maximumInterval: "30s",
+  maximumAttempts: 8,
+} as const
+const FAILURE_ACTIVITY_RETRY = {
+  initialInterval: "1s",
+  backoffCoefficient: 2,
+  maximumInterval: "10s",
+  maximumAttempts: 3,
+} as const
 
 class WorkflowControlTerminationError extends Error {
   readonly alreadyMarkedFailed: boolean
@@ -120,15 +133,11 @@ export async function oneshotOrchestrationWorkflow(input: OrchestrationWorkflowI
   const workflowActivities = proxyActivities<typeof activities>({
     startToCloseTimeout: "8 hours",
     heartbeatTimeout: ACTIVITY_HEARTBEAT_TIMEOUT,
-    retry: {
-      maximumAttempts: 1,
-    },
+    retry: ORCHESTRATION_ACTIVITY_RETRY,
   })
   const failureActivities = proxyActivities<typeof activities>({
     startToCloseTimeout: "1 minute",
-    retry: {
-      maximumAttempts: 1,
-    },
+    retry: FAILURE_ACTIVITY_RETRY,
   })
 
   const state: WorkflowExecutionState = {
@@ -429,6 +438,16 @@ export async function oneshotOrchestrationWorkflow(input: OrchestrationWorkflowI
     if (error instanceof WorkflowControlTerminationError && error.alreadyMarkedFailed) {
       throw error
     }
+    if (isRecoverableInfrastructureFault(error)) {
+      const reason = summarizeRecoveryError(error)
+      const pauseReason = `Workflow auto-paused for system recovery: ${reason}`
+      state.pauseRequested = true
+      state.note = pauseReason
+      await failureActivities.markRunPausedActivity(input, pauseReason).catch(() => {})
+      await drainRunningChildren(running, WORKFLOW_CANCEL_DRAIN_TIMEOUT_MS)
+      state.activeChildTaskIds = []
+      return { runId: input.runId }
+    }
     const reason = error instanceof Error ? error.message : String(error)
     await failureActivities.markRunFailedActivity(input, `Workflow failed: ${reason}`).catch(() => {})
     throw error
@@ -441,9 +460,7 @@ export async function oneshotAgentTaskWorkflow(
   const workflowActivities = proxyActivities<typeof activities>({
     startToCloseTimeout: "8 hours",
     heartbeatTimeout: ACTIVITY_HEARTBEAT_TIMEOUT,
-    retry: {
-      maximumAttempts: 1,
-    },
+    retry: ORCHESTRATION_ACTIVITY_RETRY,
   })
 
   const result = await workflowActivities.executeTaskActivity({
diff --git a/packages/oneshot/src/orchestrator/runtime/worktree-ingest.ts b/packages/oneshot/src/orchestrator/runtime/worktree-ingest.ts
index e367b1d..7391f07 100644
--- a/packages/oneshot/src/orchestrator/runtime/worktree-ingest.ts
+++ b/packages/oneshot/src/orchestrator/runtime/worktree-ingest.ts
@@ -31,6 +31,7 @@ const COMMIT_STAGE_EXCLUDED_PATH_PATTERNS = [
 const LOCKFILE_BASENAMES = new Set(["package-lock.json", "yarn.lock", "pnpm-lock.yaml", "bun.lockb"])
 const PACKAGE_MANIFEST_BASENAME = "package.json"
 const CONFLICT_MARKER_PATTERN = "^(<<<<<<<|=======|>>>>>>>)"
+const ensuredRepoCache = new Map<string, { repoRoot: string; initializedRepository: boolean }>()
 
 export interface PreparedTaskWorktree {
   repoRoot: string
@@ -193,39 +194,60 @@ export async function ensureGitRepoForOrchestration(projectRoot: string): Promis
   repoRoot: string
   initializedRepository: boolean
 }> {
-  const lockKey = `orchestrator.repo.init.${path.resolve(projectRoot)}`
+  const normalizedProjectRoot = path.resolve(projectRoot)
+  const cached = ensuredRepoCache.get(normalizedProjectRoot)
+  if (cached) {
+    return {
+      repoRoot: cached.repoRoot,
+      initializedRepository: false,
+    }
+  }
+
+  const lockKey = `orchestrator.repo.init.${normalizedProjectRoot}`
   using _lock = await Lock.write(lockKey)
 
-  const existingRoot = await gitTopLevel(projectRoot)
+  const cachedAfterLock = ensuredRepoCache.get(normalizedProjectRoot)
+  if (cachedAfterLock) {
+    return {
+      repoRoot: cachedAfterLock.repoRoot,
+      initializedRepository: false,
+    }
+  }
+
+  const existingRoot = await gitTopLevel(normalizedProjectRoot)
   if (existingRoot) {
+    ensuredRepoCache.set(normalizedProjectRoot, {
+      repoRoot: existingRoot,
+      initializedRepository: false,
+    })
     return {
       repoRoot: existingRoot,
       initializedRepository: false,
     }
   }
 
-  const initMain = await runGit(["init", "-b", "main"], projectRoot)
+  const initMain = await runGit(["init", "-b", "main"], normalizedProjectRoot)
   if (initMain.exitCode !== 0) {
-    const fallback = await runGit(["init"], projectRoot)
+    const fallback = await runGit(["init"], normalizedProjectRoot)
     if (fallback.exitCode !== 0) {
       throw new Error(`Failed to initialize git repository: ${message(fallback) || message(initMain)}`)
     }
   }
 
-  await ensureProjectPolicyConfig(projectRoot)
+  await ensureProjectPolicyConfig(normalizedProjectRoot)
 
-  const projectEntries = await readdir(projectRoot, { withFileTypes: true }).catch(() => [])
+  const projectEntries = await readdir(normalizedProjectRoot, { withFileTypes: true }).catch(() => [])
   const pathspecs = projectEntries
     .filter((entry) => entry.name !== ".git" && entry.name !== ".oneshot" && entry.name !== ".DS_Store")
     .map((entry) => entry.name)
   if (pathspecs.length > 0) {
-    const addProjectFiles = await runGit(["add", "-A", "--", ...pathspecs], projectRoot)
+    const addProjectFiles = await runGit(["add", "-A", "--", ...pathspecs], normalizedProjectRoot)
     if (addProjectFiles.exitCode !== 0) {
       throw new Error(`Failed to stage project files for initial repository snapshot: ${message(addProjectFiles)}`)
     }
   }
 
-  const addPolicy = await runGit(["add", "--", PROJECT_POLICY_CONFIG_RELATIVE_PATH], projectRoot)
+  const addPolicy = await runGit(["add", "--", PROJECT_POLICY_CONFIG_RELATIVE_PATH], normalizedProjectRoot)
   if (addPolicy.exitCode !== 0) {
     throw new Error(`Failed to stage project policy profile: ${message(addPolicy)}`)
   }
@@ -241,17 +263,22 @@ export async function ensureGitRepoForOrchestration(projectRoot: string): Promis
       "-m",
       "chore: initialize repository for oneshot orchestration",
     ],
-    projectRoot,
+    normalizedProjectRoot,
   )
   if (commit.exitCode !== 0) {
     throw new Error(`Failed to create initial git commit: ${message(commit)}`)
   }
 
-  const repoRoot = await gitTopLevel(projectRoot)
+  const repoRoot = await gitTopLevel(normalizedProjectRoot)
   if (!repoRoot) {
     throw new Error("Git repository initialized but top-level path could not be resolved")
   }
 
+  ensuredRepoCache.set(normalizedProjectRoot, {
+    repoRoot,
+    initializedRepository: true,
+  })
+
   return {
     repoRoot,
     initializedRepository: true,
diff --git a/packages/oneshot/test/orchestrator/checklist-expansion.test.ts b/packages/oneshot/test/orchestrator/checklist-expansion.test.ts
new file mode 100644
index 0000000..c4891f5
--- /dev/null
+++ b/packages/oneshot/test/orchestrator/checklist-expansion.test.ts
@@ -0,0 +1,38 @@
+import { describe, expect, test } from "bun:test"
+import { ChecklistExpansionInternals } from "../../src/orchestrator/runtime/langgraph-engine"
+
+describe("remediation checklist expansion", () => {
+  test("detects command-like checklist steps", () => {
+    expect(ChecklistExpansionInternals.isCommandLikeChecklistStepForTesting("Run npm install")).toBe(true)
+    expect(ChecklistExpansionInternals.isCommandLikeChecklistStepForTesting("npx prisma db push")).toBe(true)
+    expect(ChecklistExpansionInternals.isCommandLikeChecklistStepForTesting("Validate schema migrations")).toBe(false)
+  })
+
+  test("coalesces consecutive terminal commands into one execution step", () => {
+    const steps = [
+      "Run npm install",
+      "Run npx prisma generate",
+      "Run npx prisma db push",
+      "Validate schema types",
+      "Update remediation notes",
+    ]
+
+    const coalesced = ChecklistExpansionInternals.coalesceChecklistStepsForTesting(steps)
+    expect(coalesced).toHaveLength(3)
+    expect(coalesced[0]).toContain("Run command sequence:")
+    expect(coalesced[0]).toContain("1. Run npm install")
+    expect(coalesced[0]).toContain("3. Run npx prisma db push")
+    expect(coalesced[1]).toBe("Validate schema types")
+  })
+
+  test("keeps single command steps as-is", () => {
+    const steps = [
+      "Run npm install",
+      "Validate build output",
+      "Run npm test",
+    ]
+
+    const coalesced = ChecklistExpansionInternals.coalesceChecklistStepsForTesting(steps)
+    expect(coalesced).toEqual(steps)
+  })
+})
diff --git a/packages/oneshot/test/orchestrator/recovery-errors.test.ts b/packages/oneshot/test/orchestrator/recovery-errors.test.ts
new file mode 100644
index 0000000..9ba3c7a
--- /dev/null
+++ b/packages/oneshot/test/orchestrator/recovery-errors.test.ts
@@ -0,0 +1,37 @@
+import { describe, expect, test } from "bun:test"
+import {
+  collectErrorMessages,
+  isRecoverableInfrastructureFault,
+  summarizeRecoveryError,
+} from "../../src/orchestrator/runtime/recovery"
+
+describe("orchestrator runtime recovery classification", () => {
+  test("extracts nested failure details", () => {
+    const failure = {
+      message: "Activity task failed",
+      cause: {
+        message: "EAGAIN: resource temporarily unavailable, posix_spawn '/opt/homebrew/bin/git'",
+      },
+    }
+    const messages = collectErrorMessages(failure)
+    expect(messages.some((message) => message.includes("Activity task failed"))).toBe(true)
+    expect(messages.some((message) => message.includes("EAGAIN"))).toBe(true)
+  })
+
+  test("classifies transient infra faults as recoverable", () => {
+    const error = new Error("EAGAIN: resource temporarily unavailable, posix_spawn '/opt/homebrew/bin/git'")
+    expect(isRecoverableInfrastructureFault(error)).toBe(true)
+  })
+
+  test("treats generic activity failures as recoverable continuity faults", () => {
+    expect(isRecoverableInfrastructureFault(new Error("Activity task failed"))).toBe(true)
+  })
+
+  test("summary prefers concrete root cause over generic wrapper", () => {
+    const failure = {
+      message: "Activity task failed",
+      cause: { message: "EAGAIN: resource temporarily unavailable, posix_spawn '/opt/homebrew/bin/git'" },
+    }
+    expect(summarizeRecoveryError(failure)).toContain("EAGAIN")
+  })
+})
diff --git a/packages/oneshot/test/orchestrator/replan-decision-sanitization.test.ts b/packages/oneshot/test/orchestrator/replan-decision-sanitization.test.ts
index 7af9f27..bd011f9 100644
--- a/packages/oneshot/test/orchestrator/replan-decision-sanitization.test.ts
+++ b/packages/oneshot/test/orchestrator/replan-decision-sanitization.test.ts
@@ -332,4 +332,111 @@ describe("supervisor replan decision sanitization", () => {
     expect(deps).toContain("impl-core")
     expect(deps).toContain("validation")
   })
+
+  test("convergence guard prunes unanchored additions under queue pressure", () => {
+    const failedTask = createTask({
+      id: "api-core",
+      name: "Implement API core",
+      status: "failed",
+      error: "Task model prompt timed out after 600000ms",
+    })
+    const pendingTasks = Array.from({ length: 24 }, (_, index) =>
+      createTask({
+        id: `pending-${index + 1}`,
+        name: `Pending task ${index + 1}`,
+        status: "pending",
+      }))
+    const graph = buildGraph([failedTask, ...pendingTasks])
+    graph.replanCount = 6
+
+    const constrained = ReplanDecisionInternals.constrainReplanDecisionForConvergence({
+      graph,
+      decision: {
+        shouldReplan: true,
+        reasoning: "Add more workstreams.",
+        tasksToAdd: [
+          {
+            id: "new-dashboard-overhaul",
+            name: "Dashboard overhaul",
+            description: "Rebuild the dashboard experience end to end.",
+            kind: "implementation",
+            dependencies: [],
+            acceptanceCriteria: [],
+            files: [],
+          },
+          {
+            id: "new-theme-system",
+            name: "Theme system rewrite",
+            description: "Introduce a new global theme architecture.",
+            kind: "implementation",
+            dependencies: [],
+            acceptanceCriteria: [],
+            files: [],
+          },
+        ],
+        tasksToRetry: [],
+        tasksToSkip: [],
+      },
+      failedTasks: [failedTask],
+      failedGates: [],
+      remainingTokens: 30_000,
+      averageTokensPerTask: 75_000,
+    })
+
+    expect(constrained.tasksToAdd).toHaveLength(0)
+  })
+
+  test("convergence guard keeps anchored additions while pruning unrelated growth", () => {
+    const failedTask = createTask({
+      id: "api-core",
+      name: "Implement API core",
+      status: "failed",
+      error: "Task model prompt timed out after 600000ms",
+    })
+    const pendingTasks = Array.from({ length: 18 }, (_, index) =>
+      createTask({
+        id: `pending-${index + 1}`,
+        name: `Pending task ${index + 1}`,
+        status: "pending",
+      }))
+    const graph = buildGraph([failedTask, ...pendingTasks])
+    graph.replanCount = 5
+
+    const constrained = ReplanDecisionInternals.constrainReplanDecisionForConvergence({
+      graph,
+      decision: {
+        shouldReplan: true,
+        reasoning: "Split failures and add polish work.",
+        tasksToAdd: [
+          {
+            id: "api-core-split",
+            name: "Split API core failure into focused patches",
+            description: "Decompose API core into smaller recoverable implementation tasks.",
+            parentTaskId: "api-core",
+            kind: "orchestration",
+            dependencies: [],
+            acceptanceCriteria: [],
+            files: [],
+          },
+          {
+            id: "sitewide-polish",
+            name: "Sitewide polish",
+            description: "Add broad UI polish improvements across the app.",
+            kind: "implementation",
+            dependencies: [],
+            acceptanceCriteria: [],
+            files: [],
+          },
+        ],
+        tasksToRetry: [],
+        tasksToSkip: [],
+      },
+      failedTasks: [failedTask],
+      failedGates: [],
+      remainingTokens: 25_000,
+      averageTokensPerTask: 60_000,
+    })
+
+    expect(constrained.tasksToAdd.map((task) => task.id)).toEqual(["api-core-split"])
+  })
 })
diff --git a/packages/oneshot/test/orchestrator/verification.test.ts b/packages/oneshot/test/orchestrator/verification.test.ts
index fec5f21..958ce72 100644
--- a/packages/oneshot/test/orchestrator/verification.test.ts
+++ b/packages/oneshot/test/orchestrator/verification.test.ts
@@ -213,6 +213,51 @@ describe("orchestrator deterministic verification", () => {
     expect(outside?.summary.toLowerCase()).toContain("outside")
   })
 
+  test("rebases absolute worktree paths back into the project root", async () => {
+    await using tmp = await tmpdir()
+    const relPath = path.join("frontend", "src", "utils", "date.ts")
+    const filePath = path.join(tmp.path, relPath)
+    await mkdir(path.dirname(filePath), { recursive: true })
+    await Bun.write(filePath, "export const formatDate = (value: string) => value\n")
+
+    const fakeWorkerAbsolutePath = path.join(
+      tmp.path,
+      ".oneshot",
+      "worktrees",
+      "run-abc",
+      "task-xyz",
+      relPath,
+    )
+
+    const spec: Orchestrator.VerificationSpec = {
+      checks: [
+        {
+          id: "date-util-exists",
+          type: "file_exists",
+          path: fakeWorkerAbsolutePath,
+          assertions: ["date util exists"],
+          required: true,
+        },
+        {
+          id: "date-util-export",
+          type: "file_contains",
+          path: fakeWorkerAbsolutePath,
+          contains: ["formatDate"],
+          assertions: ["date util exports formatDate"],
+          required: true,
+        },
+      ],
+      retryPolicy: {
+        maxFixAttempts: 2,
+        requireProgress: true,
+      },
+    }
+
+    const result = await runVerificationSpec({ projectRoot: tmp.path, spec })
+    expect(result.passed).toBe(true)
+    expect(result.checkResults.every((item) => item.passed)).toBe(true)
+  })
+
   test("isolates command verification in git worktree to avoid mutating repo root", async () => {
     const isolationDisabled = ["0", "false", "no", "off"].includes(
       (process.env.ONESHOT_VERIFICATION_ISOLATE_WORKTREE ?? "").trim().toLowerCase(),