diff --git a/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts b/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
index c5c82fc5736..ca4107fb309 100644
--- a/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
+++ b/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
@@ -673,11 +673,14 @@ class ExtensionsContributions extends Disposable implements IWorkbenchContributi
 			],
 			icon: installWorkspaceRecommendedIcon,
 			run: async () => {
+				const outdated = this.extensionsWorkbenchService.outdated;
 				const results = await this.extensionsWorkbenchService.updateAll();
 				results.forEach((result) => {
-					if (result.error && result.context?.extension) {
-						const extension: IExtension = result.context.extension;
-						runAction(this.instantiationService.createInstance(PromptExtensionInstallFailureAction, extension, extension.latestVersion, InstallOperation.Update, result.error));
+					if (result.error && result.context?.extensionIdentifier) {
+						const extension: IExtension | undefined = outdated.find((extension) => extension.identifier === result.context?.extensionIdentifier);
+						if (extension) {
+							runAction(this.instantiationService.createInstance(PromptExtensionInstallFailureAction, extension, extension.latestVersion, InstallOperation.Update, result.error));
+						}
 					}
 				});
 			}
diff --git a/src/vs/workbench/contrib/extensions/browser/extensionsWorkbenchService.ts b/src/vs/workbench/contrib/extensions/browser/extensionsWorkbenchService.ts
index ae61ff5b04d..7e2a2660d0b 100644
--- a/src/vs/workbench/contrib/extensions/browser/extensionsWorkbenchService.ts
+++ b/src/vs/workbench/contrib/extensions/browser/extensionsWorkbenchService.ts
@@ -1375,7 +1375,7 @@ export class ExtensionsWorkbenchService extends Disposable implements IExtension
 						installPreReleaseVersion: extension.local?.isPreReleaseVersion,
 						profileLocation: this.userDataProfileService.currentProfile.extensionsResource,
 						donotIncludePackAndDependencies: true,
-						context: { extension }, // Provide extension as context in result so result reporting can use its properties
+						context: { extensionIdentifier: extension.identifier }, // Provide this in result so result reporting can look it up and use its properties
 					}
 				});
 			}