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This has been introduced in this commit: https://github.com/jenkinsci/jenkins/commit/7335916f
I'd like to submit a PR, but I'm not sure about the best way to fix this. I've removed the lock on the Queue in CloudRetentionStrategy in my local repo, and have been running that code for 3 days without a deadlock occurring. The commit message implies that more refactoring is to come around Queue locking, so I don't want to interfere with that plan.
I've seen that other deadlocks involving RetentionStrategy.check() have been fixed by converting the synchronized method to using a ReentrantLock. But the ones I've seen don't do anything if the lock cannot be obtained. In this case, I don't think the methods should return without doing anything.
So, some of the ideas I have:
Are there any other options? If not, which would be the best approach?