For the failure case, is it possible that multiple links were posted in the same message? If so, it currently only shows the link preview for the first link. This is an issue we’ve considered improving here: [MM-42135] - Mattermost
@it33_mattermost could this be a possibility? We’ve internally tried to reproduce this in many different environment and automated it to post several links quickly in order to rule out any race conditions but so far we haven’t been able to reproduce.