Android App & Plex Web Can No Longer Connect to Server on Wifi

Device 1: Pixel 5a
OS: Android 13 (Build TQ3A.230805.001.A2)
Plex App Version: 9.29.1.3463 (1a71eb3)

Device 2: Desktop PC
OS: Windows 10 Home 22H2 (Build 19045.3324)
Plex Version: Web - 4.113.2
Browser: Tried Chrome and Edge

As of sometime after August 1st, neither plex.tv nor any android device on my home wifi can connect to a friend’s server (or any other server I have access to). The server owners all confirmed nothing has changed on their ends, and nobody else is having the same issue.

Likewise, nothing has changed with my home wifi (I’m positive) or my ISP (no way to know for sure of course) in the last month.

Findings:
1. On Android, the servers are marked offline. If I switch to a cell network the servers appear normally.
2. On Plex.tv, I get the message “app.plex.tv is unable to connect to [server name] securely”

I have fixed #1 by changing Settings > Advanced > Allow insecure connections to “Always”. Curiously, if I toggle it back to “Never” (which is what I’ve had it set to for years), the servers remain connected and visible.

To fix #2, I had to download Plex for Windows. Everything works flawlessly there.

My question: does anyone know what changed?

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