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Hello,
Tim here and I work on the Connect Support Team at AWS Premium Support.
I was checking on my end on how I could help but It'd require some account specific items to best troubleshoot. On the support case you created you'll want to share the debug logs which will give us timestamps and request id information. If you're using the AWS CLI the debugging logs can be enabled by following the steps here: https://docs.aws.amazon.com/cli/latest/userguide/cli-chap-troubleshooting.html#general-debug
Another key item is checking CloudTrail as there may be some additional information that may not bubble back up towards the AWS CLI commands logging (maybe something further downstream for example).
My apologies for not following up on this earlier. Support did get back to me and logically it didn't make any sense. If I did a "list" of associations on my end nothing showed. However, support looked at it and stated there was already Wisdom association showing. I then listed again and sure enough it showed. I have no idea why. Deleted that association and created with no further issues.
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