[codex] Structure desktop SSH prompt presentation failures

[juliusmarminge]

Summary

• record the exact Electron window operation for SSH prompt presentation failures
• attach request correlation and window-availability stage data while preserving original causes
• stop throwing typed errors inside Effect.try and keep failed prompt cleanup reliable

Verification

• vp test apps/desktop/src/ssh/DesktopSshPasswordPrompts.test.ts apps/desktop/src/ssh/DesktopSshEnvironment.test.ts
• vp check (passes with 20 existing warnings)
• vp run typecheck

---

Note

Medium Risk
Touches SSH authentication UX and error mapping in the desktop app; behavior changes around edge cases (window state, renderer send failures) but is well covered by new tests.

Overview
Desktop SSH password prompts now classify failures by which Electron step failed and when the window became unavailable, instead of lumping everything into one generic window-unavailable path.

DesktopSshPromptPresentationError gains an operation label (e.g. send-prompt-request, check-window-before-request) and nullable requestId; DesktopSshPromptWindowUnavailableError adds stage (before-request, after-send, etc.) and richer messages. The request() flow is split into labeled steps via runPresentationOperation, avoids throwing typed errors inside Effect.try, and uses Effect.ensuring so pending prompts and window close listeners are always cleaned up.

If the user submits a password before a later presentation step throws, preferSubmittedPassword still returns the password instead of failing the request. New tests cover renderer send failures, pre-request window checks, cleanup after failed delivery, and the late-failure + early-resolve case.

^{Reviewed by Cursor Bugbot for commit 32a8c28. Bugbot is set up for automated code reviews on this repo. Configure here.}

Note

Structure SSH prompt presentation failures by operation and stage in desktop

• DesktopSshPromptPresentationError now includes a required operation field (e.g. 'check-window-before-request', 'send-prompt-request') and allows a nullable requestId for failures that occur before an ID is generated.
• DesktopSshPromptWindowUnavailableError now carries a stage field ('before-request', 'before-presentation', 'after-send', 'after-restore') and a requestId, with a dynamic message that includes stage and destination context.
• request() in DesktopSshPasswordPrompts.ts now performs staged window checks and wraps each presentation step in a runPresentationOperation helper that attaches the specific failing operation to any thrown error.
• If a presentation step fails after a password has already been submitted, the implementation returns the submitted password rather than failing.
• Behavioral Change: window unavailability and presentation errors now carry structured metadata; error messages include stage/destination context instead of a shared constant string.

^{Macroscope summarized 32a8c28.}

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---

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[macroscopeapp]

Approvability

Verdict: Approved

Error handling improvements for SSH prompt presentation failures with structured operation classification. The author owns this code, changes are well-tested, and the runtime behavior change (preserving already-submitted passwords) is a robustness fix rather than new feature logic.

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Dismissing prior approval to re-evaluate 5ee7cfe

[cursor]

Cursor Bugbot has reviewed your changes using high effort and found 1 potential issue.

Bugbot Autofix prepared a fix for the issue found in the latest run.

• ✅ Fixed: Staged yields lose resolved password
  • Wrapped the post-send presentation operations (window destroy checks, restore, focus) in an inner Effect.gen with Effect.ignore so their failures cannot shadow an already-resolved password from the deferred, while the window-closed listener and timeout still handle genuinely-gone windows.

Or push these changes by commenting:

@cursor push a7d1f74ac1

Preview (a7d1f74ac1)

diff --git a/apps/desktop/src/ssh/DesktopSshPasswordPrompts.ts b/apps/desktop/src/ssh/DesktopSshPasswordPrompts.ts
--- a/apps/desktop/src/ssh/DesktopSshPasswordPrompts.ts
+++ b/apps/desktop/src/ssh/DesktopSshPasswordPrompts.ts
@@ -413,34 +413,42 @@
       yield* runPresentationOperation("send-prompt-request", () =>
         window.value.webContents.send(SSH_PASSWORD_PROMPT_CHANNEL, promptRequest),
       );
-      const unavailableAfterSend = yield* runPresentationOperation("check-window-after-send", () =>
-        window.value.isDestroyed(),
-      );
-      if (unavailableAfterSend) {
-        return yield* new DesktopSshPromptWindowUnavailableError({
-          destination: input.destination,
-          requestId,
-          stage: "after-send",
-        });
-      }
-      const minimized = yield* runPresentationOperation("check-window-minimized", () =>
-        window.value.isMinimized(),
-      );
-      if (minimized) {
-        yield* runPresentationOperation("restore-window", () => window.value.restore());
-      }
-      const unavailableAfterRestore = yield* runPresentationOperation(
-        "check-window-after-restore",
-        () => window.value.isDestroyed(),
-      );
-      if (unavailableAfterRestore) {
-        return yield* new DesktopSshPromptWindowUnavailableError({
-          destination: input.destination,
-          requestId,
-          stage: "after-restore",
-        });
-      }
-      yield* runPresentationOperation("focus-window", () => window.value.focus());
+      // Once the prompt is sent the renderer can resolve the password at any
+      // scheduling boundary. The remaining steps only improve visibility
+      // (focus / restore) so their failures must not shadow an already-resolved
+      // password. Wrap them as best-effort; the window-closed listener and
+      // timeout still protect against a truly-gone window.
+      yield* Effect.gen(function* () {
+        const unavailableAfterSend = yield* runPresentationOperation(
+          "check-window-after-send",
+          () => window.value.isDestroyed(),
+        );
+        if (unavailableAfterSend) {
+          return yield* new DesktopSshPromptWindowUnavailableError({
+            destination: input.destination,
+            requestId,
+            stage: "after-send",
+          });
+        }
+        const minimized = yield* runPresentationOperation("check-window-minimized", () =>
+          window.value.isMinimized(),
+        );
+        if (minimized) {
+          yield* runPresentationOperation("restore-window", () => window.value.restore());
+        }
+        const unavailableAfterRestore = yield* runPresentationOperation(
+          "check-window-after-restore",
+          () => window.value.isDestroyed(),
+        );
+        if (unavailableAfterRestore) {
+          return yield* new DesktopSshPromptWindowUnavailableError({
+            destination: input.destination,
+            requestId,
+            stage: "after-restore",
+          });
+        }
+        yield* runPresentationOperation("focus-window", () => window.value.focus());
+      }).pipe(Effect.ignore);
       return yield* waitForPassword;
     }).pipe(Effect.ensuring(cleanup));
   });

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