Thanks for the reply and suggestions, I really appreciate it -
Only http, https does not work (neither https://192.168.1.22:32400/ on my Mac, nor https://127.0.0.1:32400/web/ in a VNC session to the RPI work).
I tried this, using a VNC session to the RPI and 127.0.0.1:32400/web, and an SSH session on the RPI. I have to log in at https://plex.tv/claim, I get a token, but after exactly 1 minute curl returns a 500/server error:
curl -X POST http://127.0.0.1:32400/myplex/claim?token=claim-....
<html><head><title>Internal Server Error</title></head><body><h1>500 Internal Server Error</h1></body></html>
I repeated the process and watched the logs, in case it tells you anything I had to log in again at https://plex.tv/claim, I mean the log in from a few minutes previously is not remembered.
Plex Media Server.Log entries from this attempt:
Feb 21, 2022 14:12:07.256 [0xb2590d48] DEBUG - Request: [127.0.0.1:51868 (Loopback)] POST /myplex/claim?token=xxxxxxxxxxxxxxxxxxxxygERFZ (2 live)
Feb 21, 2022 14:12:07.257 [0xb2590d48] DEBUG - HTTP requesting POST https://plex.tv/api/claim/exchange?token=xxxxxxxxxxxxxxxxxxxxygERFZ
Feb 21, 2022 14:12:22.272 [0xb27f1d48] DEBUG - [HttpClient] HTTP simulating 408 after curl timeout
Feb 21, 2022 14:12:22.272 [0xb2590d48] DEBUG - MyPlex: Did token exchange for claim (returnCode: 408)
Feb 21, 2022 14:12:22.274 [0xb2590d48] DEBUG - MyPlex: Got a token poked, let’s act on it.
Feb 21, 2022 14:12:22.274 [0xb2590d48] DEBUG - HTTP requesting GET https://plex.tv/api/v2/user/privacy?X-Plex-Token=
Feb 21, 2022 14:12:37.290 [0xb27f1d48] DEBUG - [HttpClient] HTTP simulating 408 after curl timeout
Feb 21, 2022 14:12:37.291 [0xb2590d48] WARN - [Analytics] Couldn’t get analytics privacy settings. Trying again soon.
Feb 21, 2022 14:12:37.292 [0xb2590d48] DEBUG - HTTP requesting GET https://plex.tv/api/v2/release_channels?X-Plex-Token=
Feb 21, 2022 14:12:52.308 [0xb27f1d48] DEBUG - [HttpClient] HTTP simulating 408 after curl timeout
Feb 21, 2022 14:12:52.309 [0xb2590d48] WARN - [AutoUpdateRequestHandler] Couldn’t get update channels. Trying again soon.
Feb 21, 2022 14:12:52.309 [0xb2590d48] DEBUG - Sync: onMyPlexSignOut
Feb 21, 2022 14:12:52.310 [0xb2590d48] DEBUG - HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token=
Feb 21, 2022 14:13:07.322 [0xb27f1d48] DEBUG - [HttpClient] HTTP simulating 408 after curl timeout
Feb 21, 2022 14:13:07.323 [0xb2590d48] WARN - FeatureManager: Couldn’t get features. Trying again soon.
Feb 21, 2022 14:13:07.323 [0xb2abad48] DEBUG - Completed: [127.0.0.1:51868] 500 POST /myplex/claim?token=xxxxxxxxxxxxxxxxxxxxygERFZ (2 live) 60067ms 325 bytes (pipelined: 1)
Feb 21, 2022 14:13:07.323 [0xb2611d48] DEBUG - HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token=>
FWIW it is only Plex that seems to not be able to reach the internet, from a shell on the RPI there is no problem, eg:
$ curl -v "https://plex.tv/updater/products/5/check.xml?build=linux-armv7neon&channel=16&distribution=debian&version=1.25.5.5492-12f6b8c83"
* Trying 18.203.229.213:443...
* Connected to plex.tv (18.203.229.213) port 443 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
* successfully set certificate verify locations:
* CAfile: /etc/ssl/certs/ca-certificates.crt
* CApath: /etc/ssl/certs
* TLSv1.3 (OUT), TLS handshake, Client hello (1):
* TLSv1.3 (IN), TLS handshake, Server hello (2):
* TLSv1.3 (IN), TLS handshake, Encrypted Extensions (8):
* TLSv1.3 (IN), TLS handshake, Certificate (11):
* TLSv1.3 (IN), TLS handshake, CERT verify (15):
* TLSv1.3 (IN), TLS handshake, Finished (20):
* TLSv1.3 (OUT), TLS change cipher, Change cipher spec (1):
* TLSv1.3 (OUT), TLS handshake, Finished (20):
* SSL connection using TLSv1.3 / TLS_AES_128_GCM_SHA256
* ALPN, server accepted to use h2
* Server certificate:
* subject: C=CH; ST=Nidwalden; L=Stans; O=Plex GmbH; CN=*.plex.tv
* start date: Sep 22 00:00:00 2021 GMT
* expire date: Sep 22 23:59:59 2022 GMT
* subjectAltName: host "plex.tv" matched cert's "plex.tv"
* issuer: C=US; O=DigiCert Inc; CN=DigiCert TLS RSA SHA256 2020 CA1
* SSL certificate verify ok.
* Using HTTP2, server supports multi-use
* Connection state changed (HTTP/2 confirmed)
* Copying HTTP/2 data in stream buffer to connection buffer after upgrade: len=0
* Using Stream ID: 1 (easy handle 0x2fed20)
> GET /updater/products/5/check.xml?build=linux-armv7neon&channel=16&distribution=debian&version=1.25.5.5492-12f6b8c83 HTTP/2
> Host: plex.tv
> user-agent: curl/7.74.0
> accept: */*
>
* TLSv1.3 (IN), TLS handshake, Newsession Ticket (4):
* Connection state changed (MAX_CONCURRENT_STREAMS == 250)!
< HTTP/2 200
< cache-control: max-age=0, private, must-revalidate
< content-type: application/xml; charset=utf-8
< date: Mon, 21 Feb 2022 03:19:49 GMT
< etag: W/"62ffe10e5613908d0900ccec21f7517c"
< referrer-policy: origin-when-cross-origin
< strict-transport-security: max-age=31536000; includeSubDomains; preload
< vary: Origin
< x-content-type-options: nosniff
< x-frame-options: SAMEORIGIN
< x-request-id: a69a02c7-fc83-41b2-ad7c-8629309ff7d8
< x-runtime: 0.101556
< x-xss-protection: 1; mode=block
<
<?xml version="1.0" encoding="UTF-8"?>
<MediaContainer friendlyName="myPlex" identifier="com.plexapp.plugins.myplex" machineIdentifier="7ba08832d0a3cf23690a7cedb0c948a6b90aee1d" size="0" title="Updates">
</MediaContainer>
* Connection #0 to host plex.tv left intact
(I notice the returned machineIdentifier is not one of the identifiers in my Preferences.xml, in case that is relevant).
Thanks again for your help.