chore(shared): bump managed cloudflared to 2026.10.0

[bompus]

What Changed

Bump the managed T3 Connect relay client from cloudflared 2026.5.2 to 2026.10.0. Update the version, all five release URLs and SHA-256 pins, and the relay install-dialog test fixtures.

All five checksums were computed from downloaded release assets and match GitHub's asset digests. The Linux and Windows values also match the release notes. The Darwin release-notes hashes cover the extracted binaries; the installer verifies the .tgz archives, so its pins use the archive hashes.

Why

The managed pin is several releases behind. Since 2026.9.3, the release changes add DNS retries and cancellation of pending QUIC request-body reads. The path-normalization change is disabled by default and leaves the request forwarded to the origin untouched.

macOS verification

Mike retested both 2026.9.3 and 2026.10.0 on the same macOS 27.0 arm64 host that initially failed. Both versions connected normally: /ready reached readyConnections: 4, and a client on another machine reached the environment through the relay. He also verified that 2026.9.3 worked after a full quit and relaunch of T3 Code.

The original failure's cause remains unknown. Mike found that 2026.5.2 also logs Trust evaluate failure, so that line does not establish a version-specific failure. The 2026.10.0 release notes do not claim a fix for it.

A search of cloudflare/cloudflared issues found no exact match for the original trust errors. #1736 concerns a different macOS QUIC TLS failure on older releases; #1751's author retracted the version-regression claim; #1725 concerns executable code signing.

Verification

• packages/shared/src/relayClient.test.ts and apps/web/src/cloud/relayClientInstallDialog.test.ts: 8/8 passed.
• Shared-package tsc --noEmit, targeted lint, formatting, and git diff --check: passed.
• Downloaded and hashed all five supported release assets; both Darwin tarballs contain cloudflared and their extracted binary hashes match the release notes.
• Linux amd64 binary reports cloudflared version 2026.10.0.
• Contributor-tested macOS 27.0 arm64 tunnel connectivity, readiness, and relay access, as linked above.
• No live tunnel connection tested locally or on Windows; macOS x64 remains untested.

Checklist

• This PR is small and focused
• I explained what changed and why
• I included before/after screenshots for any UI changes
• I included a video for animation/interaction changes

[macroscopeapp]

Approvability

Verdict: Not approved

Macroscope's review found this PR not approvable — This PR updates the default managed cloudflared executable and its integrity pins, changing the binary used for future relay installations. Because it changes a product default and cross-platform tunnel behavior was not fully verified, human review is required.

^{You can add or adjust custom eligibility rules. Learn more.}

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📝 Walkthrough

Walkthrough

The managed Cloudflared client now uses version 2026.9.1. Release URLs and checksums were updated for supported platforms. Installation dialog tests now assert the updated versions and conflict message.

Changes

Cloudflared release update

Layer / File(s)	Summary
Managed release metadata packages/shared/src/relayClient.ts	Updates the Cloudflared version, release asset URLs, and pinned SHA-256 checksums to 2026.9.1.
Installation dialog test expectations apps/web/src/cloud/relayClientInstallDialog.test.ts	Updates confirmation, progress, declined-installation, closing-view, and concurrent-confirmation tests for the new versions.

Priority: ⬇️ Low

Estimated code review effort: 2 (Simple) | ~10 minutes

Change: Other

Merge Risk: ⚪ Minimal · up to 0d713

The release metadata and updated dialog expectations are consistent, with no actionable merge-blocking risk remaining.

🚥 Pre-merge checks | ✅ 3 | ❌ 2

❌ Failed checks (2 warnings)

Check name	Status	Explanation	Resolution
Title check	⚠️ Warning	The title identifies the managed cloudflared version bump, but it says 2026.10.0 while the file-change summary reports that the managed client was updated to 2026.9.1.	Update the title to match the version implemented in the changes, or update the implementation so it matches the title.
Description check	⚠️ Warning	The description explains the change and verification in detail, but its claimed target version (2026.10.0) conflicts with the file-change summary (2026.9.1) and the PR objectives (2026.9.0). It …	Confirm the version implemented, then align the description, title, and PR objectives. Add the triaged issue or maintainer approval for the scope, or explain why this focused change qualifies for the template's exemption.

✅ Passed checks (3 passed)

Check name	Status	Explanation
Docstring Coverage	✅ Passed	No functions found in the changed files to evaluate docstring coverage. Skipping docstring coverage check. Docstring coverage is scoped to functions touched by this diff. Analyzed 0 functions across 2…
Linked Issues check	✅ Passed	Check skipped because no linked issues were found for this pull request.
Out of Scope Changes check	✅ Passed	Check skipped because no linked issues were found for this pull request.

Full details: Description check

Explanation

The description explains the change and verification in detail, but its claimed target version (2026.10.0) conflicts with the file-change summary (2026.9.1) and the PR objectives (2026.9.0). It also omits the required scope and approval information or an explanation for why approval is not needed.

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Actionable comments posted: 1

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Inline comments:
In `@packages/shared/src/relayClient.ts`:
- Line 76: Update the macOS asset digest pins in CLOUDFLARED_RELEASE_ASSETS to
use the uploaded release digests: set arm64 to
c0eccb3758420d1f4e46cbf2b8ecde01d9802a154232a817f25133340009fcc7 and amd64 to
8f2ecf41776d942bcc8070a56e7bafa4c5de70a1d1781110e2eb3774cca512a8.

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[mwolson]

A heads-up from one macOS host before the pin moves: on macOS 27.0 (arm64), cloudflared 2026.9.3 could not open any new tunnel connection. Every attempt logged Trust evaluate failure: [leaf MissingIntermediate OtherTrustValidityPeriod] in the unified log, cloudflared's /ready stayed at readyConnections: 0, and clients got "Relay could not reach the environment endpoint (endpoint_request_failed)". Putting the pinned 2026.5.2 back fixed it within seconds. Two Linux hosts ran 2026.9.3 and 2026.8.2 without trouble.

It's a single Mac, so it may be something about that machine, but it seems worth confirming that a macOS host can connect on 2026.9.3 before bumping the pin. (That Mac had 2026.9.3 because the managed binary updated itself in place, before #9386 added --no-autoupdate.)

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Sent by Mike's agent (Claude Opus 5.5)

[bompus]

@mwolson I updated this PR to cloudflared 2026.10.0. Could you test that version on the affected macOS 27.0 arm64 host when it is safe to interrupt the tunnel?

Please check whether it establishes new tunnel connections, whether /ready reports nonzero readyConnections, and whether a relay client can reach the environment. It would also help to know whether the unified log still shows Trust evaluate failure: [leaf MissingIntermediate OtherTrustValidityPeriod]. If it fails, does restoring 2026.5.2 recover connectivity again?

I found no cloudflare/cloudflared issue matching those trust errors. #1736 reports a different macOS QUIC TLS failure on older versions, and #1751's author retracted the version-regression claim. The 2026.10.0 changes do not claim a fix for this trust failure.

The asset hashes and focused tests pass, but macOS tunnel connectivity remains unverified. I'm holding off on landing this PR pending your test result.

[mwolson]

@bompus I retested on the same macOS 27.0 arm64 host, and both 2026.9.3 and 2026.10.0 connected normally: /ready reached readyConnections: 4, and a client on another machine reached the environment through the relay. 2026.9.3 also held up through a full quit and relaunch of T3 Code, which is when it failed before.

The cause of the original failure is still unknown. The Trust evaluate failure line turned out to be noise, since 2026.5.2 logs it too, and nothing else from that run points to the version. So it's probably fine to ship 2026.10.0.

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Sent by Mike's agent (Claude Opus 5.5)

[mwolson]

Closing the loop on this, Julius merged #16648 and #16649 which fixed the problems I had, so definitely doesn't need to block this PR.