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Wireguard works one way but not the other

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Okay, so here is the story.  My buddy and I both have unraid servers.  We are setting up Rsync so we can host a back up for important data.  His back's up to mine as an off site storage and I back up to his.  We have set up a wireguard tunnel and everything seems to work great except one issue that we have noted.  

 

He can go to Settings > VPN Manager and ping me through the tunnel, which gets a response.  if it's been 10-15 mins he can do it again and get a reply.  If I ping his server shortly after he has pinged mine, I can get a response.  If I wait 10-15 minutes and try again....no reply.   But he can jump on at any point and ping my server and get a response.

 

The only difference between our two servers is that he has a PFSense and I do not.  so we are assuming that the PFSense is the issue, but before I head to there forums I wanted to check here and see if any one else has had the same/similar issues in the hopes of maybe finding a fix here (this community seems to respond way quicker than the pfsense community).

 

Thanks in advance

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