This is a clone of issue OCPBUGS-23514. The following is the description of the original issue:
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Description of problem:

Upgrade of the ota-stage cluster from 4.14.1 to 4.15.0-ec.2 got stuck because of the operator-lifecycle-manager-packageserver ClusterOperator which never reaches the desired version (likely because its Pods are CrashLooping, which is a separate issue discussed now on Slack and OCPBUGS-23538 was filed for it)

However, I would expect CVO to enter its waiting for operator-lifecycle-manager-packageserver up to 40 minutes state, eventually hit that deadline and signal the upgrade as stuck via a Failing=True condition, but that did not happen and CVO does not signal anything problematic in this stuck state.

Version-Release number of selected component (if applicable):

upgrade from 4.14.1 to 4.15.0-ec.2

How reproducible:

Unsure

Steps to Reproduce:

1. upgrade from 4.14.1 to 4.15.0-ec.2 and hope you get stuck the way ota-stage did

Actual results:

$ OC_ENABLE_CMD_UPGRADE_STATUS=true ./oc adm upgrade status
An update is in progress for 2h8m20s: Working towards 4.15.0-ec.2: 695 of 863 done (80% complete), waiting on operator-lifecycle-manager-packageserver

Expected results:

$ oc adm upgrade status
Failing=True
  Reason: operator-lifecycle-manager-packageserver is stuck (or whatever is the message)

An update is in progress for 2h8m20s: Working towards 4.15.0-ec.2: 695 of 863 done (80% complete), waiting on operator-lifecycle-manager-packageserver

Additional info

Attached CVO log and the waited-on CO yaml dump