I think that was a transient issue caused by me disconnecting and reconnecting a VPN and is not related to the issue with Plex. Attached is another set of logs I just got where that same message is only present in several instances at the same timestamp. What would be the connection with the API rate limit error when attempting to pull a certificate? Also, this message appears a ton of times:
Jul 02, 2021 18:35:50.371 [0x7f1ee3fc5b38] DEBUG - Request: [108.6.218.222:63188] rejected because secure connections are require
Could it be a similar issue to this case? "API rate limit exceeded" When Getting Certificate