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[Apache] Reverse SSL Proxy not working

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Dearest community,

For testing purposes I have only one vhost configured with the purpose of hosting my plex server behind an apache reverse proxy over SSL. The config looks like this:

ServerSignature Off
ServerTokens Prod

<VirtualHost *:80>
  ServerName plex.privatedomain.com
  # This VirtualHost redirects everything to HTTPS on port 443.
  RewriteEngine On
  RewriteCond %{HTTPS} off
  RewriteRule (.*) https://%{HTTP_HOST}%{REQUEST_URI}
</VirtualHost>

<VirtualHost *:443>
  ServerName plex.privatedomain.com
  ServerAlias ""
  Options -Includes -ExecCGI

  RewriteEngine On
  RewriteCond %{THE_REQUEST} !HTTP/1.1$
  RewriteRule .* - [F]

  LimitRequestBody 512000
  SSLEngine On
  SSLCertificateFile /etc/letsencrypt/live/movies.privatedomain.com/fullchain.pem
  SSLCertificateKeyFile /etc/letsencrypt/live/movies.privatedomain.com/privkey.pem
  SSLProtocol +TLSv1.2

  Header always set Strict-Transport-Security "max-age=63072000; includeSubdomains; preload"
  Header always set X-Frame-Options DENY
  FileETag None
  TraceEnable off
  #Header edit Set-Cookie ^(.*)$ ;HttpOnly;Secure
  Header set X-XSS-Protection "1; mode=block"
  Timeout 60

    <Location /:/websockets/notifications>
        ProxyPass wss://localhost:32400/:/websockets/notifications
        ProxyPassReverse wss://localhost:32400/:/websockets/notifications
    </Location>

  <Proxy *>
        Order deny,allow
        Allow from all
  </Proxy>

    ProxyRequests Off
    ProxyPreserveHost On
    SSLProxyEngine On
    RequestHeader set Front-End-Https "On"
    ProxyPass / http://localhost:32400/
    ProxyPassReverse / http://localhost:32400/

    RewriteEngine on
    RewriteCond %{REQUEST_URI} !^/web
    RewriteCond %{HTTP:X-Plex-Device} ^$
    RewriteCond %{REQUEST_METHOD} !^(OPTIONS)$

    RewriteRule ^/$ /web/$1 [R,L]
</VirtualHost>

Sadly after I login my server cannot be found, see below the browser debug log. If anyone can help me figuring out what is going wrong I would be very grateful!

    myPlexAccessToken is not in VolatileWebStorage
    connections is not in PersistentWebStorage
    skipSignIn is not in PersistentWebStorage
    settingsv2 is not in PersistentWebStorage
    experience is not in PersistentWebStorage
    [UserManager] autoLogin false
    [Servers] Initializing...
    [Servers] Waiting for initial servers = [Anonymous], plex.tv
    [Primary Server] Waiting to set the primary server
    [Primary Server] Waiting for the last primary server, c13467b3a58c55650932dfdbbb32aa92d27c216b, to connect
    [Commands] Executing testServerConnection
    [Commands] Executing testServerConnection
    [Servers] Finished initialization
    [Cast] Loaded the cast api
    [Cast] No receivers are available
    [Connections] Testing connection for plex.tv at https://plex.tv/pms/:/ip
    [Connections] Testing connection for [Anonymous] at https://plex.privatedomain.com/
    [Connections] plex.tv connected at https://plex.tv/pms/:/ip
    [Connections] Active connection to plex.tv is https://plex.tv
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] [Anonymous] has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] [Anonymous] is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  [Anonymous]
    [Connections] All connections to [Anonymous] failed
    [Servers] Waiting for initial servers = plex.tv
    [Servers] Finding resources through plex.tv
    [Servers] Waiting for additional resources from plex.tv
    [CloudServerEventManager] Opening server event connection to plex.tv at wss://pubsub.plex.tv/sub/websockets/8807264/onn9jkkhqorhtzt948klf2yb9?X-Plex-Token=REDACTED
    [Companion] Registering player with plex.tv, clientID="onn9jkkhqorhtzt948klf2yb9"
    [Servers] plex.privatedomain.com was found through plex.tv
    [Commands] Executing testServerConnection
    [Servers] Waiting for additional resources from plex.tv
    [Servers] Plex server Mark was found through plex.tv
    [Commands] Executing testServerConnection
    [Servers] Waiting for additional resources from plex.tv
    [Servers] Waiting for additional resources from plex.tv
    [Servers] Found 7 resources through plex.tv
    [Servers] Found all servers = plex.tv
    [Commands] Executing lockUser
    [CloudServerEventManager] Opened server event connection to plex.tv at wss://pubsub.plex.tv/sub/websockets/8807264/onn9jkkhqorhtzt948klf2yb9?X-Plex-Token=REDACTED
    [Commands] Executing authenticateWithServer
    [Connections] Testing connection for plex.privatedomain.com at https://plex.privatedomain.com/
    [Connections] Aborting connection test for plex.privatedomain.com at http://192.168.0.240:32400/ due to mixed content prevention
    [Connections] Aborting connection test for plex.privatedomain.com at http://172.17.0.1:32400/ due to mixed content prevention
    [Connections] Testing connection for Plex server Mark at https://192-168-2-11.8c9fa4cb80ca4953a6d5dc9b49a95621.plex.direct:32400/
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] plex.privatedomain.com has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] plex.privatedomain.com is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  plex.privatedomain.com
    [Connections] All connections to plex.privatedomain.com failed
    [Servers] Found all servers = plex.tv
    [Primary Server] Waiting for any owned server to connect
    [Primary Server] Waiting for any eligible server to connect
    [Companion] No proxy found
    [Commands] Executing switchUser
    [Commands] Executing authenticateWithServer
    [Commands] Executing resetUser
    [Connections] Aborted pending connection test for Plex server Mark at https://192-168-2-11.8c9fa4cb80ca4953a6d5dc9b49a95621.plex.direct:32400/
    [Servers] Found all servers = plex.tv
    [CloudServerEventManager] Closing server event connection to plex.tv at wss://pubsub.plex.tv/sub/websockets/8807264/onn9jkkhqorhtzt948klf2yb9?X-Plex-Token=REDACTED
    [Servers] Resetting...
    [Servers] Initializing...
    [Servers] Waiting for initial servers = [Anonymous]
    [Primary Server] Waiting for the last primary server, c13467b3a58c55650932dfdbbb32aa92d27c216b, to connect
    [Commands] Executing testServerConnection
    [Servers] Finished initialization
    [Servers] Finding resources through plex.tv
    [Servers] Waiting for initial servers = [Anonymous]
    [CloudServerEventManager] Opening server event connection to plex.tv at wss://pubsub.plex.tv/sub/websockets/8807264/onn9jkkhqorhtzt948klf2yb9?X-Plex-Token=REDACTED
    [Commands] Executing resumePlayQueue
    [Commands] Executing persistPlayQueue
    [Servers] plex.privatedomain.com was found through plex.tv
    [Commands] Executing testServerConnection
    [Connections] Aborting connection test for plex.privatedomain.com at http://192.168.0.240:32400/ due to mixed content prevention
    [Connections] Testing connection for [Anonymous] at https://plex.privatedomain.com/
    [Commands] Executing testServerConnection
    [Servers] Waiting for initial servers = [Anonymous]
    [Servers] Plex server Mark was found through plex.tv
    [Commands] Executing testServerConnection
    [Connections] Testing connection for plex.privatedomain.com at https://plex.privatedomain.com/
    [Connections] Aborting connection test for plex.privatedomain.com at http://172.17.0.1:32400/ due to mixed content prevention
    [Connections] Testing connection for Plex server Mark at https://192-168-2-11.8c9fa4cb80ca4953a6d5dc9b49a95621.plex.direct:32400/
    [Servers] Waiting for initial servers = [Anonymous]
    [Servers] Waiting for initial servers = [Anonymous]
    [Servers] Found 7 resources through plex.tv
    [Servers] Waiting for initial servers = [Anonymous]
    [CloudServerEventManager] Opened server event connection to plex.tv at wss://pubsub.plex.tv/sub/websockets/8807264/onn9jkkhqorhtzt948klf2yb9?X-Plex-Token=REDACTED
    [Servers] Populate any server chose plex.tv where servers = [Anonymous], plex.privatedomain.com, plex.tv, Plex server Mark
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] [Anonymous] has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] [Anonymous] is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  [Anonymous]
    [Connections] All connections to [Anonymous] failed
    [Servers] Found all servers = plex.tv
    [Parser] Errors found while parsing XML document
    [Connections] plex.privatedomain.com has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] plex.privatedomain.com is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  plex.privatedomain.com
    [Connections] All connections to plex.privatedomain.com failed
    [Servers] Found all servers = plex.tv
    [Primary Server] Waiting for any owned server to connect
    [Primary Server] Waiting for any eligible server to connect
    [Companion] No proxy found
    [Connections] Plex server Mark is unavailable at https://192-168-2-11.8c9fa4cb80ca4953a6d5dc9b49a95621.plex.direct:32400/ (Status 0)
    [Connections] Prevented fallback to insecure connection for  Plex server Mark
    [Connections] All connections to Plex server Mark failed
    [Servers] Found all servers = plex.tv
    [Primary Server] Waiting for any eligible server
    [Connections] Retrying connection tests for plex.privatedomain.com in 1 seconds
    [Connections] Retrying server events connection for plex.privatedomain.com in 1 seconds
    [Primary Server] plex.privatedomain.com is now the primary server
    [Connections] Testing all 3 connection(s) for plex.privatedomain.com
    [Servers] Found all servers = plex.tv
    [Commands] Executing testServerConnection
    [Connections] Aborting connection test for plex.privatedomain.com at http://192.168.0.240:32400/ due to mixed content prevention
    [Commands] Executing testServerConnection
    [Connections] Retrying connection tests for plex.privatedomain.com in 2 seconds
    [Connections] Retrying server events connection for plex.privatedomain.com in 2 seconds
    [Connections] All connections to plex.privatedomain.com failed
    [Servers] Found all servers = plex.tv
    [Connections] Testing connection for plex.privatedomain.com at https://plex.privatedomain.com/
    [Connections] Aborting connection test for plex.privatedomain.com at http://172.17.0.1:32400/ due to mixed content prevention
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] plex.privatedomain.com has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] plex.privatedomain.com is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  plex.privatedomain.com
    [Connections] All connections to plex.privatedomain.com failed
    [Companion] No proxy found
    [Connections] Testing all 3 connection(s) for plex.privatedomain.com
    [Servers] Found all servers = plex.tv
    [Commands] Executing testServerConnection
    [Connections] Retrying connection tests for plex.privatedomain.com in 3 seconds
    [Connections] Retrying server events connection for plex.privatedomain.com in 3 seconds
    [Connections] Testing connection for plex.privatedomain.com at https://plex.privatedomain.com/
    [Connections] Aborting connection test for plex.privatedomain.com at http://192.168.0.240:32400/ due to mixed content prevention
    [Connections] Aborting connection test for plex.privatedomain.com at http://172.17.0.1:32400/ due to mixed content prevention
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] plex.privatedomain.com has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] plex.privatedomain.com is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  plex.privatedomain.com
    [Connections] All connections to plex.privatedomain.com failed
    [Servers] Found all servers = plex.tv
    [Connections] Testing all 3 connection(s) for plex.privatedomain.com
    [Servers] Found all servers = plex.tv
    [Commands] Executing testServerConnection
    [Connections] Retrying connection tests for plex.privatedomain.com in 4 seconds
    [Connections] Retrying server events connection for plex.privatedomain.com in 4 seconds
    [Connections] Testing connection for plex.privatedomain.com at https://plex.privatedomain.com/
    [Connections] Aborting connection test for plex.privatedomain.com at http://192.168.0.240:32400/ due to mixed content prevention
    [Connections] Aborting connection test for plex.privatedomain.com at http://172.17.0.1:32400/ due to mixed content prevention
    Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This content should also be served over HTTPS.
    [Parser] Errors found while parsing XML document
    [Connections] plex.privatedomain.com has an unexpected machine identifier at https://plex.privatedomain.com/
    [Connections] plex.privatedomain.com is unavailable at https://plex.privatedomain.com/ (Status 200)
    [Connections] Prevented fallback to insecure connection for  plex.privatedomain.com
    [Connections] All connections to plex.privatedomain.com failed
    [Servers] Found all servers = plex.tv

My eye was falling on the following log entries:
Mixed Content: The page at 'https://plex.privatedomain.com/web/index.html' was loaded over HTTPS, but requested an insecure XMLHttpRequest endpoint 'http://plex.privatedomain.com/web/index.html'. This request has been blocked; the content must be served over HTTPS.

In my Chrome browser I did allow this though:
You have recently allowed insecure content (such as scripts or iframes) to run on this site.

Any thoughts?


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