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AI recovery agent breaks after rolling back and then reapplying server upgrades #10013

@Rose-Northey

Description

@Rose-Northey

Severity

Edge case

Version

rolling back to before 2026.1.5108 and then updating to after this version

Latest Version

None

What happened?

AI recovery agent stops working after rolling back and then reapplying server upgrades.
This results in an attempt to reregister the same license which does not succeed. Registrations must be reset by octopus when this happens.

Reproduction

Upgrade Server to a version with AIProxy registration (post 2026.1.5108)→ roll back to before this → re-upgrade to the same (or newer) version. Re-registration call returns 409 Conflict because the license is already registered with AIProxy.

Error and Stacktrace

“409 Conflict” AIProxy registration check failed for user XXX”
Unhandled error on request: "AI Proxy service is not available. Please contact your administrator."
System.UnauthorizedAccessException: AI Proxy service is not available. Please contact your administrator.
Failure path: Octopus.Server.Web.Controllers.Tasks.Bff.DiagnoseDeploymentFailureController.DiagnoseDeploymentFailure

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Workaround

Octopus must be contacted to reset the license.

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