For anyone coming across this topic. I never managed to solve this issue. I had to workaround using a WD NAS I already had.

@akuma1x It's more that I did not want some of the naming / descriptions public, none of which should matter for troubleshooting. Cheers!

@FrankZappa Fire up Wireshark or Packet Capture to see what's on the wire. If it works with the Asus router, but not pfsense, it's likely a filter issue. It's hard to say though, without knowing what's actually happening. Since it worked with the Asus router, it's probably not using broadcast or multicast.

Have you checked into this information? https://pfsense-docs.readthedocs.io/en/latest/usermanager/plain-mac-authentication-with-freeradius.html I have not had a chance to test it. Hope it helps.

@provels i have same thing on 2.4.5p1 and i see it has existed for a long time

A little added info, if I try to ping 192.168.1.10 (Test Client 1) from 192.168.1.20 (Test Client 2) while running tcpdump on both pfsense, I see ARP traffic: [2.4.5-RELEASE][root@TestFW01.localdomain]/root: tcpdump -nibridge0 host 192.168.1.20 tcpdump: verbose output suppressed, use -v or -vv for full protocol decode listening on bridge0, link-type EN10MB (Ethernet), capture size 262144 bytes 08:48:23.031203 ARP, Request who-has 192.168.1.1 tell 192.168.1.20, length 46 08:48:24.028594 ARP, Request who-has 192.168.1.1 tell 192.168.1.20, length 46 08:48:25.028870 ARP, Request who-has 192.168.1.1 tell 192.168.1.20, length 46 [2.4.5-RELEASE][root@TestFW02.localdomain]/root: tcpdump -nibridge0 host 192.168.1.20 tcpdump: verbose output suppressed, use -v or -vv for full protocol decode listening on bridge0, link-type EN10MB (Ethernet), capture size 262144 bytes 08:48:33.036875 ARP, Request who-has 192.168.1.1 tell 192.168.1.20, length 46 08:48:33.037605 ARP, Reply 192.168.1.1 is-at 00:bd:79:1a:ff:01, length 28 08:48:34.036904 ARP, Request who-has 192.168.1.1 tell 192.168.1.20, length 46 08:48:34.037940 ARP, Reply 192.168.1.1 is-at 00:bd:79:1a:ff:01, length 28 If I run the same tcpdump command, substituting the ovpn interface for bridge0, I see ARP requests and replies on both pfsense. I'm not sure who is the owner of 00:bd:79:1a:ff:01, but it doesn't appear in the ARP table of either pfsense, and I get no result for it on either hwaddress.com or maclookup.app. edit: typo

ah ok thats what i guess'd because the linux lite is a 32bit version and maybe the ubuntu.. i got these dell servers and i couldnt afford to build my son a computer prices went up for certain parts even 2x4s gone up 300 percent damn pandemic but figured since it couldnt run windows 10 i get linux and then he could connect to my network.. but guess cant but least the linux lite will connect to the internet.. Windows XP doesnt seem to connect anymroe so i scrapped that .. these were super computers back in the day lol

My config screenshot didn't work, obviously. Here's a link: https://ibb.co/BnW2nWp

Thank you, It was indeed the unneeded client that was asking for the password.

@barakath what do u really need. what timezone u r in ? what have you done to achieve your request so far ? br nP

@Dudleydogg hi there. I just followed this doc. https://techshielder.com/how-to-setup-and-use-nordvpn-on-pfsense

@viragomann Ok, I understand, I have 2 different users but the same certificate... Thank you very much for your help !

@NogBadTheBad Thank you for the insights. I didnt even know that

Anyone having the same issue who found this via search: I have been able to replicate the issue on several devices now and I was able to stop it from happening by making the server UDP4 only, not multi-home UDP4/UDP6. Seems like a bug to me because the server does have native IPv4 and IPv6 but the only configuration change that made this issue go away was changing the server to UDP4.

No idea about your USG stuff, but you should be able to hit pfSense at 192.168.5.1 with no problem. Show your OpenVPN Config and Firewall Rules. -Rico

Here is the official doc: https://docs.netgate.com/pfsense/en/latest/book/openvpn/bridged-openvpn-connections.html -Rico

@rjamesm said in Help! OpenVPN settings will not connect no matter what I do: I've been struggling for the past couple days to get this to work, seems like a no brainier yet still difficult. Hi, This seems desperate to me ... if we get professional information we might be able to help with the issue