Episodes play on Android but not Windows/Web

Plex Media Server NAS & Devices
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Server Version#: 1.16.2.1321
Windows Player version#: 1.16.2.1321
Android Player Version#: 7.18.1.11300

I am experiencing an issue where some episodes of TV shows play on my Android phone but will not play on my Windows desktop Plex or the web player.

When I try to play them on Windows or the web player I receive the message: an unexpected error has occurred.

I have discovered that when I start the episode on a different platform then I am able to continue the episode on the windows/web player.

Any thoughts on how to approach this issue?

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