Office 365 timeouts under VPN (PIA)

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New Contributor

For security measures, I have been using VPN services for the past couple years with no issues so far, but as of recently I have been getting constant timeout requests while trying to use Office 365 services, forcing me to disconnect my VPN in order to use any O365 service whatsoever, both on web and app versions. Has there been any change in the user policies henceforth blocking the use of VPN, even regardless of geo restrictions, for I have been using only local servers, for encryption and data security only? 

I currently use Private Internet Access under a recently renewed 3y plan and I did not want to migrate to a different service if possible.

4 Replies
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@Daniel_Trefilio - Did this just start happening for you recently? My connection to O365 over PIA started being very problematic for me a few days ago. Disabling has been my only solution so far.

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It has started a few days ago, if I recall I was working from home during the weekend and didn't notice anything unusual, but Monday or Tuesday I started to get request timeouts whenever trying to access O365 services and it still has not been addressed on PIA forums and or reddit.
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Yep - Exactly the same for me. Had been working flawlessly for several months until Monday. Going to dig a bit and see what I can turn up.

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I experienced this problem with PIA name servers set to 'Handshake'. )365 reconnected when I switched to Cloudflare name servers (consistent with the settings in use before connecting PIA). Whether this is acceptable setting for security purposes, I do not know, but it is an option and is useful for troubleshooting.