Plex Unreachable or Allow Insecure Connections only

This post is meant to be an extension of Plex Unreachable or Allow Insecure Connections only as opposed to a duplicate, but I’m not sure how to go about re-opening a ticket. I tried almost everything on that thread, but none resolved my problem.

The problematic behavior I ran into was that I would run into a page where when remotely accessing my server, I would get a page that says something like “unable to connect to server, do you want to allow insecure connection?”, and when I enable insecure connection, I’m able to access and stream my media fine. The behavior was 100% reproducible. Before this happened, remote access has successfully worked without problems for a very long time. Also, a Plex media server update was not done anywhere near the timeframe of when this behavior began to occur, so I can’t reasonably say that an update on my end was the cause. I think the cert probably just expired and a new cert was never fetched.

Server Version#: 1.21.0.3711
Player Version#: 4.48.1

Logs have the following entry:
Dec 03, 2020 09:21:22.471 [3364] DEBUG - CERT: incomplete TLS handshake: sslv3 alert bad certificate

For anyone running into a similar situation, here’s what worked for me. I opened up the web client through the localhost URL, went to settings, then authorized devices, and removed each device to force them to go through client-setup again, which I believe, implies that the client fetch a valid certificate. I had a lot of devices so I ended up executing some form of the following js in a web console (on firefox, tools -> web developer -> web console):

for (remove of Array.from(document.querySelectorAll("button.remove-device-btn.card-action-btn.btn-danger")).slice(1)) {
   remove.click();
   for (confirm of document.querySelectorAll("button.confirm-btn.btn.btn-lg.btn-danger.btn-loading")) {
      confirm.click();
   }
}

// or a little bit more manually:

document.querySelectorAll("button.remove-device-btn.card-action-btn.btn-danger")[0].click();
document.querySelectorAll("button.confirm-btn.btn.btn-lg.btn-danger.btn-loading")[0].click();

Remotely accessing my server from the web client https://app.plex.tv/desktop or android seems to be secure now.

Secure connections should also be set to Preferred, at the localhost url

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