WindowsOsUpdateExtension stuck on Creating following Updates via Maintenance Schedule

Question

Following a failed/timed out batch of updates performed via Maintenance Schedules, several machine Extensions are stuck on 'Creating' and any subsequent attempts at updates fail due to the stuck extension.

We can eventually force the removal of the extension by restarting the services on the affected machine and waiting for the extension to fail and then removing.

Across the 6 machines currently affected, 3 were rebooted and 3 failed to reboot. All of them are now 'stuck'. The issue is spread across a variety of Windows Server, ranging from 2012R2 all the way up to 2022.

Sample properties below from Resource Graph:

telemetryLogs.log

{
    "provisioningState": "Creating",
    "type": "WindowsOsUpdateExtension",
    "autoUpgradeMinorVersion": false,
    "typeHandlerVersion": "1.0.13.0",
    "enableAutomaticUpgrade": true,
    "publisher": "Microsoft.SoftwareUpdateManagement",
    "instanceView": {
        "type": "WindowsOsUpdateExtension",
        "name": "WindowsOsUpdateExtension",
        "typeHandlerVersion": "1.0.13.0",
        "status": {
            "message": "Extension Message: Starting reboot operation., OperationResult: {\"activityId\":\"254d1909-e2a6-4464-a113-6f9eb5457e51\",\"inputStartTime\":\"2023-05-21T18:15:24Z\",\"lastModifiedTime\":\"2023-05-21T18:52:56Z\",\"extensionTriggerTime\":\"2023-05-21T18:15:41Z\",\"action\":\"Patching\",\"actionStatus\":\"transitioning\",\"patchServiceUsed\":\"WU\",\"assessmentDetails\":{\"rebootPending\":true,\"countByCategory\":{\"critical\":0,\"security\":1,\"updateRollup\":1,\"featurePack\":0,\"servicePack\":0,\"definition\":1,\"tools\":0,\"updates\":0,\"other\":0},\"totalCount\":3,\"patches\":\"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\",\"action\":\"Assessment\"},\"patchDetails\":{\"rebootNeeded\":true,\"rebootStatus\":\"Started\",\"maintenanceWindowExceeded\":false,\"rebootStartTime\":\"2023-05-21T18:52:56.1725022Z\",\"notSelectedPatchCount\":0,\"pendingPatchCount\":0,\"excludedPatchCount\":0,\"installedPatchCount\":3,\"failedPatchCount\":0,\"totalPatchCount\":3,\"patches\":\"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\",\"action\":\"Patching\"},\"topLevelStatusMessage\":\"Starting reboot operation.\",\"internalErrorMessage\":\"\",\"topLevelStatus\":1,\"logs\":\"i44FAA==\",\"errorCount\":0,\"failureRetryCount\":0,\"retriggerCount\":0,\"sequenceNumber\":14,\"errors\":null}",
            "level": "Information",
            "code": "transitioning"
        }
    },
    "settings": {
        "updateConfiguration": {
            "action": "Patching",
            "startTime": "2023-05-21T18:15:24.1132697Z",
            "classificationsToInclude": [
                "Critical",
                "Security",
                "Definition",
                "UpdateRollup",
                "Updates",
                "Tools"
            ],
            "excludeKbsRequiringReboot": false,
            "maximumDuration": 235,
            "activityId": "254d1909-e2a6-4464-a113-6f9eb5457e51",
            "maxPatchPublishDate": null,
            "patchesToInclude": {
                "mode": "Union",
                "updates": []
            },
            "patchesToExclude": [],
            "rebootSettings": "IfRequired"
        }
    }
}