Plex is unable (cannot install) to use my custom certificate on Synlogy

Plex Media Server NAS & Devices
1

Server Version#: 1.40.5.8921-7000

I have a Synology NAS and try to automatically renew the Let’s Encrypt certificate but I got the same Issue that was also reported here:

Oct 14, 2024 13:15:44.408 [140566517136016] DEBUG - MyPlex: using cached data for request for https://plex.tv/api/v2/server/users/features
Oct 14, 2024 13:15:44.501 [140566517136016] DEBUG - [CERT] Subject name is /CN=*.[redacted].plex.direct
Oct 14, 2024 13:15:44.501 [140566517136016] DEBUG - [CERT] Installed certificate with fingerprint [redacted]
Oct 14, 2024 13:15:44.501 [140566517136016] DEBUG - [CERT/OCSP] Stapling requests will be made to 'http://r10.o.lencr.org/'.
Oct 14, 2024 13:15:44.501 [140566517136016] INFO - [CERT/OCSP] Successfully retrieved response from cache.
Oct 14, 2024 13:15:44.527 [140566517136016] ERROR - [CERT] PKCS12_parse failed: error:11800071:PKCS12 routines::mac verify failure
Oct 14, 2024 13:15:44.528 [140566517136016] ERROR - [CERT] Found a user-provided certificate, but couldn't install it.
Oct 14, 2024 13:15:44.528 [140566517136016] DEBUG - HttpServer: Listening on IPv6 as well as IPv4.
Oct 14, 2024 13:15:44.528 [140566517136016] DEBUG - HttpServer: Listening on port 32400.
Oct 14, 2024 13:15:44.528 [140566517136016] DEBUG - HttpServer: Listening on port 32401.
Oct 14, 2024 13:15:44.529 [140566517136016] DEBUG - Running server...

So the error is only “Found a user-provided certificate, but couldn’t install it.”. I use the script from GitHub - zachg99/synology-plex-cert-autorenew: Script to automatically renew plex ssl certificate using the Synology LetsEncrypt certificate. and changed the parameters for my domain and set a password. When I log into the NAS with SSH I see that the certificate has been created.

Does anybody know why this happens? Also, maybe Plex could output more details to solve the issue, maybe it could include the original error message in the output.

2

Check the password.

3

I re-checked the password and the one in Plex matched the one I entered in the script. I then removed the password and now it works. Don’t know exactly why, maybe missing " or some other pitfall.
But for me it’s OK, I can live without a cert password.

4

The Plex/web field where you enter the password can EASILY get a leading space.

It’s a bugger in that you don’t see it either due to variable width font used.

I don’t use a password on these certs either. If someone breaks through my firewall (pfsense), I have bigger issues to deal with. :slight_smile:

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