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@gsnider2195 I would think make it asynchronous because it would entirely get around any concerns with timeouts but if it's not possible or would require an entire rewrite, a significantly shorter timeout would be fine.
FYI in certain environments we are also seeing Nautobot fail the post_upgrade because the SSL cert at nautobot.cloud... I suspect in these environments the organization proxies ssl traffic or for whatever reason doesn't trust the Let's Encrypt CAs. In any case I feel like these errors should be non-blocking and silently ignored, maybe just a warning
Environment
Steps to Reproduce
Expected Behavior
Nautobot starts up as quickly as usual, with either asynchronous communication to Nautobot cloud or an aggressive timeout.
Observed Behavior
Nautobot hangs for at least 5 minutes, I just disabled the setting at that point.
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