fix(desktop): replace a stale staged update with the newest release

[waleedlatif1]

Summary

• Once an update reached ready, the updater stopped checking. A shell left running across several releases installed the stale staged build on restart, then immediately offered the next one — so users updated twice in a row
• ready updates now keep re-checking on the normal cadence; a strictly newer release downloads in the background and replaces the staged one (Squirrel.Mac keeps the staged bundle while re-checking, and relaunchToInstallUpdate installs whatever is staged, so restarting mid-replacement stays safe)
• Background re-checks never clobber a ready/available update: equal versions, update-not-available, network errors, and failed replacement downloads all keep the current update
• available offers (auto-download off, and manual-download builds) also refresh to the newest release so "Update" never fetches a superseded version
• Restart confirmation installs whatever is staged instead of dropping the click when a replacement finished while the prompt was open
• Known Squirrel.Mac limitation, unchanged: a reboot before quitting drops the pending ShipIt job, so the same version is offered again on next launch (served from the updater cache, no network download)

Type of Change

• Bug fix

Testing

• Added state-machine tests for replacement, re-check failure/no-op, auto-download off, prompt race, and manual-mode refresh; 4 fail without the fix
• Desktop suite (1663 tests), tsc, lint, and check:audits pass

Checklist

• Code follows project style guidelines
• Self-reviewed my changes
• Tests added/updated and passing
• No new warnings introduced
• I confirm that I have read and agree to the terms outlined in the Contributor License Agreement (CLA)

🤖 Generated with Claude Code

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1 Skipped Deployment

Project	Deployment	Actions	Updated
docs	Skipped		Sep 23, 2026 2:11am UTC

[cubic-dev-ai]

All reported issues were addressed across 3 files

<sub>Reply with feedback, questions, or to request a fix.

Fix all with cubic | Re-trigger cubic</sub>

[greptile-apps]

Confidence Score: 5/5

The PR appears safe to merge; no outstanding correctness, security, or repository-rule violations remain.

Summary

This PR keeps staged and offered desktop updates refreshed so users install the newest eligible release rather than a stale update.

• Periodically re-checks staged and offered updates while preserving the existing update on no-op checks and failures.
• Uses Squirrel.Mac’s native staging event to distinguish downloaded replacements from installable bundles.
• Keeps restart confirmation valid when a replacement finishes staging while the prompt is open.
• Adds state-machine coverage for replacement, cancellation, rollback, failure, and manual-download behavior.

Diagram

%%{init: {'theme': 'neutral'}}%%
flowchart TD
  Offered[Offered or staged update] --> Check[Scheduled feed re-check]
  Check --> Invalid{Valid eligible release?}
  Invalid -->|No or check fails| Preserve[Preserve current offer or staged bundle]
  Invalid -->|Yes| State{Current state}
  State -->|Available| Refresh[Refresh offer to feed candidate]
  State -->|Ready and strictly newer| Download[Download replacement]
  Download --> Native[Squirrel stages replacement]
  Native --> Ready[Mark replacement ready]
  Ready --> Restart[Install staged bundle on restart]

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_{Reviews (3) · Last reviewed commit: "fix(desktop): clear a cancelled update r..."}

[waleedlatif1]

@greptile

[waleedlatif1]

@cubic-dev-ai review this PR

[cubic-dev-ai]

@cubic-dev-ai review this PR

@waleedlatif1 I have started the AI code review. It will take a few minutes to complete.

[cubic-dev-ai]

All reported issues were addressed across 4 files

<sub>Reply with feedback, questions, or to request a fix.

Fix all with cubic | Re-trigger cubic</sub>

[waleedlatif1]

@greptile

[waleedlatif1]

@cubic-dev-ai review this PR

[cubic-dev-ai]

@cubic-dev-ai review this PR

@waleedlatif1 I have started the AI code review. It will take a few minutes to complete.

[cubic-dev-ai]

No issues found across 4 files

Confidence score: 5/5

• Automated review surfaced no issues in the provided summaries.
• No files require special attention.

_{Re-trigger cubic}