I deployed a brand new VCSA on version 6.5 recently. I updated the certificates to use my own certificate authority instead of the VMware self-signed certs.
When I try to use VUM to upgrade my ESXi hosts to 6.5 I'm unable to upload the iso through VUM.
When trying to upload the process starts and then fails with this screen and that's it.
I opened the request.log file from VUM on the VCSA and receive these "500" internal server errors.
I don't see any KB articles about this issue, but did find this post on reddit related to the same issue.vCSA 6.5 Update Manager Cannot Upload ISO : vmware
The article there suggests that the replaced Certificates could cause VUM to not be working properly. I found that I had issues with NSX connecting as well after I updated the certificates so I ran through this KB article to fix that issue: https://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=2132645
It did not fix the VUM issue
I'm hoping to find out if this is a bug and if anyone has found a workaround for this issue. Moreover, if VMware will be doing anything to fix these certificate problems.