Tailscale with pfsense exit node, no DNS

[jacobhall]

I believe I am experiencing the same issue. I recently set up a fresh tailnet and added pfsense as an exit node. The exit node works except when Tailscale DNS is enabled on the client, in which case DNS breaks. This problem doesn't occur when other exit nodes are used.

Package Versions:
headscale 0.25.1
pfSense-pkg-Tailscale 0.1.4
tailscale (freebsd pkg on pfsense) 1.80.3

[jacobhall]

Linking relevant threads on the Tailscale GitHub and Lawrence Systems forum which describe related issues (it looks like @Soloam has participated in all of these).

If anyone having a similar problem bumps into this, please take a minute to document your experience so that we can collect more information and try to solve this. Thanks

[Soloam]

@jacobhall said in Tailscale with pfsense exit node, no DNS:

Linking relevant threads on the Tailscale GitHub and Lawrence Systems forum which describe related issues (it looks like @Soloam has participated in all of these).

If anyone having a similar problem bumps into this, please take a minute to document your experience so that we can collect more information and try to solve this. Thanks

This problem, from what I can tell, only happens on people using headscale, because we have to change the tailscale client version on pfsense...With Tailscale services the tailscale client on the pfsense package works and it seams to be imune to this problem

[elvisimprsntr]

Not sure if related, but there are some TestFlight builds which include DNS fixes.

[jacobhall]

@elvisimprsntr I'd be willing to try it out. When my client uses pfSense as an exit node, it can ping 100.100.100.100, but DNS queries to the same IP address time out. This makes me think there is an issue with the pfSense/FreeBSD implementation specifically.

[elvisimprsntr]

I don't seem to have a problem with DNS when using pfSense or NAS docker container as an exit node, but I am not using headscale.

PFSENSE

• 2.7.2 CE
• Tailscale package 1.4.0
• Tailscale 1.80.3_1
• Advertise sub-net routes and exit node enabled
• Accept DNS from control server enabled

NAS

• TrueNAS SCALE 24.10.2
• Tailscale docker app 1.2.14
• Tailscale 1.80.3
• Advertise sub-net routes and exit node enabled
• Accept DNS from control server enabled

ADMIN CONSOLE

• Nameservers: Magic DNS
• Global nameservers, Local DNS settings: pfSense LAN IP
• Search domains: tailnet, pfSense domain
• Advertise sub-net routes and exit node enabled for both pfSense and NAS

CLIENT

• iOS 18.4 RC
• Tailscale 1.81.193 via TestFlight

[elvisimprsntr]

1.82.0 is released with some MagicDNS fixes.

Changelog

I manually updated my NAS docker container.

tailscale update
reboot

Give it a few days for a FreeBSD package to be available.

Freshports

[jacobhall]

@elvisimprsntr I'll give it another try once that version makes it to Google Play, but at first glance this appears to be an unrelated bugfix. I have been experiencing this issue using a v1.82.0 client on Linux, which should include the patch you mention. My pfSense box is currently running 1.80.3, so maybe it's worth testing 1.80.3_1 in case that makes a difference.

I agree with @Soloam above that this is likely an issue only experienced by headscale users. Regardless, I think it's the pfSense package that requires fixing as my other exit nodes running Linux have not had any issues. I don't have the time right now to delve into the Tailscale, FreeBSD, and pfSense codebases at the moment, but I hope to support this bugfix however I can.

I am hopeful someone on this forum can help contextualize this issue in terms of pfSense's DNS system and point us (me) in the right direction for contributing a fix.

[elvisimprsntr]

I upgraded 2.7.2 CE to TS 1.82.0

No issues so far.

[Defiling2063]

@jacobhall

I was on the stock version (pfsense community 2.7.2) of tailslcale connecting to headscale.

I upgraded tailscale client on pfsense to 1.82.5 while leaving headscale unchanged. I was able to reproduce the problem -- my android tailscale client cannot resolve dns when using the tailscale client on pfsense as an exit node. If I disable "Use tailscale DNS" on my android client, internet connectivity works.

I am going to leave it broken for now, if anyone wants me to try different things. Thanks.