Server Version#: 1.32.7.7621 on raspbian
Player Version#: 4.9.2 Plexamp on iOS
When playing via plexamp, the call to the start webhook is sometimes missed\not called. (maybe more often when playing similar artist radio). Also, skipping backwards will not trigger the start webhook if the song has already been played.
Console appears to show requests# incrementing with each successful call, there is nothing indicating that a webhook call has failed. It seems like it’s not attempting to send.
When playing music via the standard plex client, start webhook is called at the beginning of every song. Including skip track forward and back.
