Plex Desktop for Mac not Playing Web Shows

Plex Players Desktop Players
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Server Version#: 1.19.1.2645
Player Version#: 1.8.0.1159-67c4a549
I am unable to play Plex Web Shows from the Mac Desktop app on the Plex server machine. Web App Works, iPhone app works and another laptop with Mac Desktop app works.

When I click on play on the web show episode the app just hangs at the player screen and not vide is ever shown.

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