Hi,
I’m also getting “unable to connect securely” issues when using app.plex.tv but it works fine when connecting directly to my server.
I’ve updated my SSL certs and regenerated the pfx file (letsencrypt) I’ve also removed the existing PFX from the Cache/ folder and verified that it regenerated the pfx in the cache on restart.
Additionally, I’ve tried manually re-claiming the server, none of these fix the issue.
My script to generate the pfx is as follow
openssl pkcs12 -export
-out plex.pfx
-in cert.pem
-inkey privkey.pem
-certfile fullchain.pem
-name [REDACTED]
-passout pass:[REDACTED]
-certpbe AES-256-CBC -keypbe AES-256-CBC -macalg SHA25
Based on the other reports, it seems like I might need a plex-side certificate refresh?
In the logs, I see an error regarding “getCertInfo” then another error about the public IP address (I’ve confirmed several times that these do in fact match between my actual IP and what I see in the remote access page of the plex config) as well as a “double NAT” error. (I for sure do not have double NAT, I do use nginx as a reverse proxy)
Thanks!
Server Version#: 1.43.3.10828
Player Version#: 4.160.0
Jul 14, 2026 19:42:23.687 [137838676921144] INFO - Plex Media Server v1.43.3.10828-00f62d37d - Ubuntu PC x86_64 - build: linux-x86_64 debian - GMT 00:00
Jul 14, 2026 19:42:23.688 [137838676921144] INFO - Linux version: 26.04 LTS (Resolute Raccoon), language: en-US
Jul 14, 2026 19:42:23.688 [137838676921144] INFO - Processor: 8-core AMD Ryzen Threadripper 3960X 24-Core Processor
Jul 14, 2026 19:42:23.688 [137838676921144] INFO - Compiler is - Clang 11.0.1 (``https://plex.tv`` 9b997da8e5b47bdb4a9425b3a3b290be393b4b1f)
Jul 14, 2026 19:42:23.688 [137838676921144] INFO - /usr/lib/plexmediaserver/Plex Media Server
Jul 14, 2026 19:42:23.734 [137838783797904] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Jul 14, 2026 19:42:23.735 [137838783797904] INFO - Running migrations. (EPG 0)
Jul 14, 2026 19:42:23.773 [137838783797904] INFO - Running migrations. (EPG 0)
Jul 14, 2026 19:42:23.776 [137838672702264] INFO - Preemptively preparing driver imd for GPU Intel DG2 [Arc A380]
Jul 14, 2026 19:42:23.776 [137838672702264] INFO - Preemptively preparing driver icr for GPU Intel DG2 [Arc A380]
Jul 14, 2026 19:42:25.057 [137838557322040] INFO - Refreshing paths watched by LibraryUpdateManager
Jul 14, 2026 19:42:25.686 [137838563650360] WARN - Crash: Crash reporting disabled
Jul 14, 2026 19:42:26.031 [137838668356408] WARN - [EventSourceClient/pubsub/pubsub05.pop.yyz.plex.bz:443] MyPlex: attempted a reachability check but we're not yet mapped.
Jul 14, 2026 19:42:28.218 [137838561540920] WARN - PublicAddressManager: WAN IP on router does not match public IP from ``plex.tv
Jul 14, 2026 19:42:31.562 [137838670465848] ERROR - [EventSourceClient/pubsub/pubsub05.pop.yyz.plex.bz:443] MyPlex: mapping failed due to potential double NAT configuration
Jul 14, 2026 19:42:36.928 [137838668356408] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Jul 14, 2026 19:42:36.931 [137838668356408] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Jul 14, 2026 19:42:38.723 [137838559431480] WARN - [HttpClient/HCl#31] HTTP error requesting GET ``https://172-17-1-52.b9e58bf4814444b2af643c5a2f5f5a13.plex.direct:32400`` (7, Couldn't connect to server) (Failed to connect to 172-17-1-52.b9e58bf4814444b2af643c5a2f5f5a13.plex.direct port 32400 after 3088 ms: Couldn't connect to server)
Jul 14, 2026 19:43:29.543 [137838490573624] WARN - WebSocket: Request doesn't look like upgrade request (, )
Jul 14, 2026 19:43:29.543 [137838490573624] WARN - Caught a system exception setting up WebSocket, ignoring.
