diff --git a/common/changes/@rushstack/heft-vscode-extension-plugin/bmiddha-vscode-tls-activation-event_2025-08-28-17-59.json b/common/changes/@rushstack/heft-vscode-extension-plugin/bmiddha-vscode-tls-activation-event_2025-08-28-17-59.json
new file mode 100644
index 00000000000..eb987016805
--- /dev/null
+++ b/common/changes/@rushstack/heft-vscode-extension-plugin/bmiddha-vscode-tls-activation-event_2025-08-28-17-59.json
@@ -0,0 +1,10 @@
+{
+  "changes": [
+    {
+      "packageName": "@rushstack/heft-vscode-extension-plugin",
+      "comment": "add extraPackagingFlags plugin option",
+      "type": "patch"
+    }
+  ],
+  "packageName": "@rushstack/heft-vscode-extension-plugin"
+}
\ No newline at end of file
diff --git a/heft-plugins/heft-vscode-extension-plugin/src/VSCodeExtensionPackagePlugin.ts b/heft-plugins/heft-vscode-extension-plugin/src/VSCodeExtensionPackagePlugin.ts
index 5bb8e63c061..ada8af53bdc 100644
--- a/heft-plugins/heft-vscode-extension-plugin/src/VSCodeExtensionPackagePlugin.ts
+++ b/heft-plugins/heft-vscode-extension-plugin/src/VSCodeExtensionPackagePlugin.ts
@@ -28,6 +28,10 @@ interface IVSCodeExtensionPackagePluginOptions {
    * This manifest is used for signing the VS Code extension.
    */
   manifestPath: string;
+  /**
+   * Additional flags to pass to the VSCE packaging command.
+   */
+  extraPackagingFlags?: string[];
 }
 
 const PLUGIN_NAME: 'vscode-extension-package-plugin' = 'vscode-extension-package-plugin';
@@ -41,7 +45,7 @@ export default class VSCodeExtensionPackagePlugin
     pluginOptions: IVSCodeExtensionPackagePluginOptions
   ): void {
     heftTaskSession.hooks.run.tapPromise(PLUGIN_NAME, async (runOptions: IHeftTaskRunHookOptions) => {
-      const { unpackedFolderPath, vsixPath, manifestPath } = pluginOptions;
+      const { unpackedFolderPath, vsixPath, manifestPath, extraPackagingFlags = [] } = pluginOptions;
       const { buildFolderPath } = heftConfiguration;
       const {
         logger: { terminal }
@@ -53,7 +57,14 @@ export default class VSCodeExtensionPackagePlugin
       const packageResult: IWaitForExitResult<string> = await executeAndWaitAsync(
         terminal,
         'node',
-        [vsceScriptPath, 'package', '--no-dependencies', '--out', path.resolve(vsixPath)],
+        [
+          vsceScriptPath,
+          'package',
+          '--no-dependencies',
+          '--out',
+          path.resolve(vsixPath),
+          ...extraPackagingFlags
+        ],
         {
           currentWorkingDirectory: path.resolve(buildFolderPath, unpackedFolderPath)
         }
diff --git a/vscode-extensions/debug-certificate-manager-vscode-extension/config/heft.json b/vscode-extensions/debug-certificate-manager-vscode-extension/config/heft.json
index e1dd458ed26..7def96a81f3 100644
--- a/vscode-extensions/debug-certificate-manager-vscode-extension/config/heft.json
+++ b/vscode-extensions/debug-certificate-manager-vscode-extension/config/heft.json
@@ -1,5 +1,19 @@
 {
   "$schema": "https://developer.microsoft.com/json-schemas/heft/v0/heft.schema.json",
 
-  "extends": "@rushstack/heft-vscode-extension-rig/profiles/default/config/heft.json"
+  "extends": "@rushstack/heft-vscode-extension-rig/profiles/default/config/heft.json",
+
+  "phasesByName": {
+    "build": {
+      "tasksByName": {
+        "package-vsix": {
+          "taskPlugin": {
+            "options": {
+              "extraPackagingFlags": ["--allow-star-activation"]
+            }
+          }
+        }
+      }
+    }
+  }
 }
diff --git a/vscode-extensions/debug-certificate-manager-vscode-extension/package.json b/vscode-extensions/debug-certificate-manager-vscode-extension/package.json
index ad94ab5c49b..8083fc5169f 100644
--- a/vscode-extensions/debug-certificate-manager-vscode-extension/package.json
+++ b/vscode-extensions/debug-certificate-manager-vscode-extension/package.json
@@ -1,6 +1,6 @@
 {
   "name": "debug-certificate-manager",
-  "version": "0.0.3",
+  "version": "0.0.4",
   "repository": {
     "type": "git",
     "url": "https://github.com/microsoft/rushstack.git",
@@ -54,7 +54,7 @@
       },
       {
         "command": "debugCertificateManager.sync",
-        "title": "Sync TLS Certificates",
+        "title": "Ensure and Sync TLS Certificates",
         "category": "Debug Certificate Manager"
       },
       {
@@ -107,7 +107,7 @@
   },
   "enabledApiProposals": [],
   "activationEvents": [
-    "workspaceContains:/.vscode/debug-certificate-manager.json"
+    "*"
   ],
   "dependencies": {
     "@rushstack/debug-certificate-manager": "workspace:*",
diff --git a/vscode-extensions/debug-certificate-manager-vscode-extension/src/extension.ts b/vscode-extensions/debug-certificate-manager-vscode-extension/src/extension.ts
index 806f7183dea..88d629431b3 100644
--- a/vscode-extensions/debug-certificate-manager-vscode-extension/src/extension.ts
+++ b/vscode-extensions/debug-certificate-manager-vscode-extension/src/extension.ts
@@ -189,9 +189,6 @@ export function activate(context: vscode.ExtensionContext): void {
           keyFilename: parsedConfig.keyFilename || 'rushstack-serve.key'
         };
       } catch (error) {
-        void vscode.window.showErrorMessage(
-          'Failed to read or parse the configuration file. Ensure that .vscode/debug-certificate-manager.json exists and is valid.'
-        );
         terminal.writeLine(
           `Error reading or parsing configuration file: ${
             error instanceof Error ? error.message : 'Unknown error'