Validated pipeline in use was set to sandbox which should allow errors on chart update check as expected.
The issue preventing the pipeline from succeeding was due to the image being set to auto which isn't allowed in our environment. This was also causing the failure in the Configuration Validation stage.
Updated image to use and set imagePullSecrets and pipeline ran cleanly:
Upgrade failed, but that's due to the fact that it was originally still using the auto image. May need to discuss this one further to see if this fix is acceptable.
Jumped on a call w/ Jimmy to discuss changes. The outstanding MR will close this story out when it's merged. Otherwise, the pipeline config changes we reviewed LGTM.