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I have been using Plex with AirVPN for some time now. My remote connection works about 30 percent of the time. I'm using windows client along with the usual port forwarding to the Plex server. Some days the remote connection works great. Other times it doesn't work for a week.  I'm not sure what else information you would need to help but I will provide whatever is needed.

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Yep, sometimes I have to go restart remote access on my plex server for it to register a new VPN server I'm using, etc.  I can't think of any other reason why it only works part of the time for you.

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The server changes in my settings automatically. But other than that everything is good on my end. It magically started working a little bit ago. 

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