Shared content doesn't load first time in playlist

Plex Players
1

Server Version#: 1.40.1.8227
Player Version#: 4.125.1

I shared some of my content with a friend who added it to a playlist with both mine and his content. If he plays the content directly it works, but if he plays it though the playlist it errors out with code S1001. If he clicks retry it works, sometimes requiring he change it to any kind of transcode setting. If he does it though any official Plex app (Windows, Linux, iOS) then it works fine, it only seems to happen in the web player

2

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