vSphere 6.7 – operation failed for an undetermined reason.

Recently I’ve upgraded a test vcenter appliance to 6.7 update 1 and found that a long standing issue is, well, an even longer standing issue.

I was attempting to deploy an OVA file via the vCenter HTML5 (and subsequently the Flex) client and was confronted with the following warning;

The operation failed for an undetermined reason. Typically this problem occurs due to certificates that the browser does not trust. If you are using self-signed or custom certificates, open the URL below in a new browser tab and accept the certificate, then retry the operation.


If this does not resolve the problem, other possible solutions are shown in this KB article:

Annoyingly, I was unable to copy and past the KB URL, but after a small amount of google use I got to the URL (as whatever I was typing in seemed to fail).

The KB article discusses numerous issues relating to the TLS/SSL certificates being used.

For me my certificates are all good, they are custom certs but valid with a number of SANs to cover all bases. However it still failed even after following the advice in the KB.

For me the final fix was to log into the WebUI of one of the ESXi 6.7 servers (which DO have self-signed certificates), and deploy the OVA via that method.

Prior to logging in I did have to accept the self-signed certificate. This was clearly the underlying issue. My vCenter has legit SSL/TLS certs issues by an internal CA, however the ESXi hosts do.

Post primarily to make my brain remember that if I hit this issue again I will remember what to do. Failing that I can search my blog :).

Featured image credit goes to: Kristine Cecilia, the image is entitled FAIL