Timeouts are tricky to debug. One option could be an infinite loop, or hitting a remote service on startup that is slow or taking a long time. Another possibility would be something like building a big index, which may not run infinitely, but if it takes more than 20 seconds we assume a timeout. Even having a huge quantity of plugins that need to be initialized can sometimes create very long boot times. One thing to try is "heroku restart", which will take another pass at trying to boot, and if the timing issue is intermittent, it might work the second time around.
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