There's an internal system we have called CPRMC (Create Pull Request Merge Commit) that is used to evaluate whether a PR is "ready" to merge. This covers everything from mergeability (checking for merge conflicts) to rule evaluations (ensuring that approvals match the potential commit that will be created by merge) and more.
This becomes particularly difficult when squash merging a stack of multiple PRs because we have to calculate a series of squashed commits, then associate those back to the rules/reviews. This is relatively easy for the first PR, but for the second PR onwards this gets more complicated because the ancestor commits are squashed and don't exist on the branch as-is. And I won't get into how much more complicated it gets for multi-parent situations lol.
It's something we need to fix and it's the top priority for the team. Our numbers show that 99% of stack merges go through successfully, but we need to get that much higher.
Thank you for being an early user in the preview and bearing with us while we work out these issues!