Fix macOS auto-update: preserve framework symlinks in the update zip (#2049)

Author: RhysSullivan

.changeset/mac-updater-zip-symlinks.md

@@ -0,0 +1,11 @@
+---
+"@executor-js/desktop": patch
+---
+
+Fix macOS auto-update. The 1.6.9 update zip was built with a 7-Zip that
+expanded the framework symlinks into copies, so the extracted app failed code
+signing and Squirrel.Mac silently refused to install it; "Restart to update"
+appeared to do nothing. electron-builder is bumped to a release that preserves
+symlinks, the publish job now verifies the zip's signature before uploading,
+and a rejected install surfaces as "Update failed" instead of leaving the card
+untouched.

.github/workflows/publish-desktop.yml

@@ -206,6 +206,37 @@ jobs:
         run: bunx --bun electron-builder --${{ matrix.platform }} --${{ matrix.arch }} --publish never --config electron-builder.config.ts
         working-directory: apps/desktop
 
+      # electron-updater installs from the zip, not the DMG, and Squirrel.Mac
+      # rejects it unless the extracted app passes codesign. 1.6.9 shipped a
+      # zip whose framework symlinks (Versions/Current -> A) had been expanded
+      # into copies by a 7-Zip upgrade inside electron-builder; the DMG was
+      # fine, every auto-update silently failed. Extract the zip the way
+      # Squirrel does and verify it before anything is uploaded.
+      - name: Verify mac update zip
+        if: matrix.platform == 'mac'
+        shell: bash
+        env:
+          CSC_LINK: ${{ secrets.CSC_LINK }}
+        run: |
+          set -euo pipefail
+          zip="apps/desktop/dist/executor-desktop-mac-${{ matrix.arch }}.zip"
+          links=$(unzip -Z "$zip" | grep -c '^l' || true)
+          echo "symlink entries in $zip: $links"
+          if [ "$links" -eq 0 ]; then
+            echo "::error::$zip has no symlink entries; framework bundles were flattened and Squirrel.Mac will reject the update"
+            exit 1
+          fi
+          # Unsigned builds (forks, no CSC_LINK) cannot pass codesign; the
+          # symlink check above still catches the flattening on its own.
+          if [ -z "${CSC_LINK:-}" ]; then
+            echo "no signing certificate configured; skipping codesign verification"
+            exit 0
+          fi
+          tmp=$(mktemp -d)
+          ditto -x -k "$zip" "$tmp"
+          codesign --verify --deep --strict --verbose=1 "$tmp/Executor.app"
+          rm -rf "$tmp"
+
       # The two mac legs each emit a latest-mac.yml listing only their own
       # arch. Rename per-arch here; the release job merges them back into the
       # single latest-mac.yml electron-updater clients fetch. Without this,

apps/desktop/package.json

@@ -48,7 +48,7 @@
     "@zip.js/zip.js": "^2.8.26",
     "bun-types": "catalog:",
     "electron": "41.10.3",
-    "electron-builder": "^26",
+    "electron-builder": "26.16.1",
     "electron-vite": "^5",
     "quickjs-emscripten": "catalog:",
     "typescript": "catalog:",

apps/desktop/src/main/index.ts

@@ -4,6 +4,7 @@ import { join } from "node:path";
 import { fileURLToPath } from "node:url";
 import {
   app,
+  autoUpdater as nativeAutoUpdater,
   BrowserWindow,
   dialog,
   ipcMain,
@@ -806,17 +807,11 @@ const registerIpcHandlers = () => {
     // Outside a packaged build there is no real bundle to swap, and quitting
     // would tear down the e2e harness — reflect "installing" so the renderer
     // can prove the wiring instead.
-    if (!app.isPackaged) {
-      setUpdateStatus({ state: "installing", version });
-      return;
-    }
-    // Stop the sidecar cleanly before Squirrel.Mac swaps the bundle, matching
-    // the native dialog's restart path.
-    stopSupervisedMonitor();
-    if (connection) {
-      await stopConnection(connection);
-      connection = null;
-    }
+    setUpdateStatus({ state: "installing", version });
+    if (!app.isPackaged) return;
+    // Squirrel.Mac only validates the staged bundle now; the sidecar is torn
+    // down in 'before-quit-for-update' once it has accepted the update, so a
+    // rejected zip leaves the app usable and surfaces via the 'error' handler.
     autoUpdater.quitAndInstall(false, true);
   });
   // Crash-screen last resort for damaged state: confirm, move the data dir
@@ -937,13 +932,7 @@ const promptInstallUpdate = async (version: string) => {
       cancelId: 1,
     });
     if (response.response === 0) {
-      // Stop the sidecar cleanly before Squirrel.Mac swaps the bundle. A
-      // supervised daemon is left running — it's independent of this bundle.
-      stopSupervisedMonitor();
-      if (connection) {
-        await stopConnection(connection);
-        connection = null;
-      }
+      setUpdateStatus({ state: "installing", version });
       autoUpdater.quitAndInstall(false, true);
       return;
     }
@@ -963,6 +952,18 @@ const setupAutoUpdater = () => {
   autoUpdater.logger = log;
   autoUpdater.autoDownload = true;
   autoUpdater.autoInstallOnAppQuit = false;
+  // Fired by Electron's native updater once Squirrel.Mac has downloaded and
+  // validated the bundle and is about to quit for the swap. Stop a spawned
+  // sidecar here rather than before quitAndInstall: if Squirrel rejects the
+  // update (bad signature, corrupt zip) nothing has been torn down. A
+  // supervised daemon is left running — it's independent of this bundle.
+  nativeAutoUpdater.on("before-quit-for-update", () => {
+    stopSupervisedMonitor();
+    if (connection) {
+      void stopConnection(connection);
+      connection = null;
+    }
+  });
 
   autoUpdater.on("update-available", (info: UpdateInfo) => {
     pendingUpdateVersion = info.version;

apps/desktop/src/main/updater-state.test.ts

@@ -79,6 +79,15 @@ describe("updater state decisions", () => {
     });
   });
 
+  it("moves a staged or installing update to error when Squirrel rejects it", () => {
+    expect(
+      statusAfterUpdateError({ state: "downloaded", version: "1.6.9" }, "Update failed"),
+    ).toEqual({ state: "error", version: "1.6.9", message: "Update failed" });
+    expect(
+      statusAfterUpdateError({ state: "installing", version: "1.6.9" }, "Update failed"),
+    ).toEqual({ state: "error", version: "1.6.9", message: "Update failed" });
+  });
+
   it("restores autoInstallOnAppQuit only when the fatal path recovers", () => {
     expect(
       planFatalAutoInstallOnQuit({

apps/desktop/src/main/updater-state.ts

@@ -89,14 +89,17 @@ export const planDownloadedUpdate = (input: DownloadedUpdateInput): DownloadedUp
   };
 };
 
+// Any state that names a version is an update in flight, including a staged
+// ("downloaded") or installing one: Squirrel.Mac validates the bundle only when
+// the install starts, so a rejected zip surfaces as an error *after* the card
+// already offered "Restart to update". Dropping that error left the card
+// unchanged and the click looked like a no-op.
 export const statusAfterUpdateError = (
   status: DesktopUpdateStatus,
   message: string,
 ): DesktopUpdateStatus => {
-  if (status.state === "available" || status.state === "downloading" || status.state === "error") {
-    return { state: "error", version: status.version, message };
-  }
-  return status;
+  if (status.state === "idle") return status;
+  return { state: "error", version: status.version, message };
 };
 
 export const planFatalAutoInstallOnQuit = (input: {