Review comments

Author: EhabY

CHANGELOG.md

@@ -4,6 +4,9 @@
 
 ### Added
 
+- Automatically set `reconnectionGraceTime`, `serverShutdownTimeout`, and `maxReconnectionAttempts`
+  on first connection to prevent disconnects during overnight workspace sleep.
+- New **Coder: Apply Recommended SSH Settings** command to overwrite all recommended SSH settings at once.
 - Proxy log directory now defaults to the extension's global storage when `coder.proxyLogDirectory`
   is not set, so SSH connection logs are always captured without manual configuration. Also respects
   the `CODER_SSH_LOG_DIR` environment variable as a fallback.

src/commands.ts

@@ -337,12 +337,20 @@ export class Commands {
 			key,
 			value: setting.value,
 		}));
-		await applySettingOverrides(
+		const ok = await applySettingOverrides(
 			this.pathResolver.getUserSettingsPath(),
 			overrides,
 			this.logger,
 		);
-		if (this.remoteWorkspaceClient) {
+		if (!ok) {
+			const action = await vscode.window.showErrorMessage(
+				"Failed to write SSH settings. Check the Coder output for details.",
+				"Show Output",
+			);
+			if (action === "Show Output") {
+				this.logger.show();
+			}
+		} else if (this.remoteWorkspaceClient) {
 			const action = await vscode.window.showInformationMessage(
 				"Applied recommended SSH settings. Reload the window for changes to take effect.",
 				"Reload Window",

src/logging/logger.ts

@@ -4,4 +4,5 @@ export interface Logger {
 	info(message: string, ...args: unknown[]): void;
 	warn(message: string, ...args: unknown[]): void;
 	error(message: string, ...args: unknown[]): void;
+	show(): void;
 }

src/remote/remote.ts

@@ -465,11 +465,16 @@ export class Remote {
 				parts.sshHost,
 				agent.operating_system,
 			);
-			await applySettingOverrides(
-				this.pathResolver.getUserSettingsPath(),
-				overrides,
-				this.logger,
-			);
+			if (overrides.length > 0) {
+				const ok = await applySettingOverrides(
+					this.pathResolver.getUserSettingsPath(),
+					overrides,
+					this.logger,
+				);
+				if (ok) {
+					this.logger.info("Settings modified successfully");
+				}
+			}
 
 			const logDir = this.getLogDir(featureSet);
 

src/remote/userSettings.ts

@@ -29,7 +29,11 @@ function recommended(
 	return { value, label: `${shortName}: ${humanized}` };
 }
 
-/** Applied by the "Apply Recommended SSH Settings" command. */
+/**
+ * Applied by the "Apply Recommended SSH Settings" command.
+ * These are more aggressive (24h) than AUTO_SETUP_DEFAULTS (8h) because the
+ * user is explicitly opting in via the command palette.
+ */
 export const RECOMMENDED_SSH_SETTINGS = {
 	"remote.SSH.connectTimeout": recommended("Connect Timeout", 1800),
 	"remote.SSH.reconnectionGraceTime": recommended(
@@ -109,7 +113,7 @@ export async function applySettingOverrides(
 	logger: Logger,
 ): Promise<boolean> {
 	if (overrides.length === 0) {
-		return false;
+		return true;
 	}
 
 	let settingsContent = "{}";

test/mocks/testHelpers.ts

@@ -391,6 +391,7 @@ export function createMockLogger(): Logger {
 		info: vi.fn(),
 		warn: vi.fn(),
 		error: vi.fn(),
+		show: vi.fn(),
 	};
 }
 

test/unit/error/serverCertificateError.test.ts

@@ -40,6 +40,7 @@ describe("Certificate errors", () => {
 		info: throwingLog,
 		warn: throwingLog,
 		error: throwingLog,
+		show: () => {},
 	};
 
 	const disposers: Array<() => void> = [];

test/unit/remote/userSettings.test.ts

@@ -160,8 +160,8 @@ describe("applySettingOverrides", () => {
 		return JSON.parse(raw) as Record<string, unknown>;
 	}
 
-	it("returns false when overrides list is empty", async () => {
-		expect(await applySettingOverrides(settingsPath, [], logger)).toBe(false);
+	it("returns true when overrides list is empty", async () => {
+		expect(await applySettingOverrides(settingsPath, [], logger)).toBe(true);
 	});
 
 	it("creates file and applies overrides when file does not exist", async () => {