From 743dbec36d2ebaa2de785410e41ef8d843bffe51 Mon Sep 17 00:00:00 2001
From: 777genius <quantjumppro@gmail.com>
Date: Thu, 16 Apr 2026 22:17:41 +0300
Subject: [PATCH] fix(extensions): surface cli healthcheck failures in action
 tooltips

---
 src/shared/utils/extensionNormalizers.ts      |  8 ++++++-
 .../shared/utils/extensionNormalizers.test.ts | 21 ++++++++++++++++---
 2 files changed, 25 insertions(+), 4 deletions(-)

diff --git a/src/shared/utils/extensionNormalizers.ts b/src/shared/utils/extensionNormalizers.ts
index a5c6420e..ecff2758 100644
--- a/src/shared/utils/extensionNormalizers.ts
+++ b/src/shared/utils/extensionNormalizers.ts
@@ -149,7 +149,10 @@ export function getInstallationSummaryLabel(
  */
 export function getExtensionActionDisableReason(options: {
   isInstalled: boolean;
-  cliStatus: Pick<CliInstallationStatus, 'installed' | 'authLoggedIn'> | null;
+  cliStatus: Pick<
+    CliInstallationStatus,
+    'installed' | 'authLoggedIn' | 'binaryPath' | 'launchError'
+  > | null;
   cliStatusLoading: boolean;
 }): string | null {
   const { isInstalled, cliStatus, cliStatusLoading } = options;
@@ -162,6 +165,9 @@ export function getExtensionActionDisableReason(options: {
   }
 
   if (cliStatus.installed === false) {
+    if (cliStatus.binaryPath && cliStatus.launchError) {
+      return 'Claude CLI was found but failed to start. Open the Dashboard to repair or reinstall it.';
+    }
     return 'Claude CLI required. Install it from the Dashboard.';
   }
 
diff --git a/test/shared/utils/extensionNormalizers.test.ts b/test/shared/utils/extensionNormalizers.test.ts
index 427a22bb..b78f1bdc 100644
--- a/test/shared/utils/extensionNormalizers.test.ts
+++ b/test/shared/utils/extensionNormalizers.test.ts
@@ -207,7 +207,7 @@ describe('getExtensionActionDisableReason', () => {
     expect(
       getExtensionActionDisableReason({
         isInstalled: false,
-        cliStatus: { installed: true, authLoggedIn: false },
+        cliStatus: { installed: true, authLoggedIn: false, binaryPath: null, launchError: null },
         cliStatusLoading: false,
       }),
     ).toContain('not signed in');
@@ -217,7 +217,7 @@ describe('getExtensionActionDisableReason', () => {
     expect(
       getExtensionActionDisableReason({
         isInstalled: true,
-        cliStatus: { installed: true, authLoggedIn: false },
+        cliStatus: { installed: true, authLoggedIn: false, binaryPath: null, launchError: null },
         cliStatusLoading: false,
       }),
     ).toBeNull();
@@ -227,11 +227,26 @@ describe('getExtensionActionDisableReason', () => {
     expect(
       getExtensionActionDisableReason({
         isInstalled: true,
-        cliStatus: { installed: false, authLoggedIn: false },
+        cliStatus: { installed: false, authLoggedIn: false, binaryPath: null, launchError: null },
         cliStatusLoading: false,
       }),
     ).toContain('Claude CLI required');
   });
+
+  it('surfaces startup health-check failures separately from missing CLI', () => {
+    expect(
+      getExtensionActionDisableReason({
+        isInstalled: false,
+        cliStatus: {
+          installed: false,
+          authLoggedIn: false,
+          binaryPath: '/usr/local/bin/claude',
+          launchError: 'spawn EACCES',
+        },
+        cliStatusLoading: false,
+      }),
+    ).toContain('failed to start');
+  });
 });
 
 describe('sanitizeMcpServerName', () => {