FreeNAS email notifications blocked by pfsense

Hi all,

Been running a FreeNAS server at home for several years now without issues. Just installed a pfsense box up front and it has blocked my daily reports outbound from FreeNAS to my google email address. I’m sure it is something simple, but I have been unsuccessful thus far. I’ve opened port 465 (SSL) to no avail. What am I missing?

not sure what you are missing, make sure the FreeNAS can get out to the internet. By default pfsense doe not do any egress filtering.

Isn’t Gmail port 587 for SMTP?

@ manipulate: I am using SSL on port 465 and have been successfully for years.

So, when I ping from FreeNAS shell as root, I can ping inside the network fine. I can ping fine. When I try to ping, I get an error:

ping: cannot resolve Host name lookup failure

I assume that it is something with DNS… pfblockerng settings perhaps?

Interestingly enough, I can access my Owncloud instance running within a freenas jail from my phone on Verizon 4G. It just seems very odd to me that I can get in from the outside, but not out from inside…

Sorry for my noob questions with pfsense. I love tinkering, but my wife has little patience. I taught myself FreeNAS and am quite comfortable with it. Running a few simple jails for Owncloud, Minecraft server for the kids, urbackup, and syncthing. We moved to a new state and my new IP was getting hammered (as indicated by my freenas security logs). pfsense was my answer… I’m determined to learn it as well (if my wife will hang in there long enough).

If you can ping from inside a jexec jail session, then you’re problem is most likely the jail network config in FreeNAS. Being able to get in to the jail from the outside is pfsense dependent, getting from the jail out, is dependent on the jail config and pfsense not blocking outbound.

Try looking at the network config from inside the jail. Shell into the jail, then run an ifconfig make sure that info is accurate. Then try a cat /etc/resolv.conf That will list what dns servers the jail is using. You can then modify it if it’s wrong (probably so), and re-test.

Either make pfsense the dns server, if it’s set up, or use whichever server(s) you want.

If you want more info on that file, or anything else, man pages are your friend. :wink:

I was actually pinging from the main Freenas shell as root. Not from inside a jail. All of freenas worked fine until I switched out my netgear nighthawk for the pfsense box. I will check / modify where freenas is pointed to for dns servers. Where should it point to?

Ahh… Drop to main FreeNAS Shell. then jls to see what jails are up and their number. Then jexec # csh to get a shell ‘inside’ the jail. That should get you going with troubleshooting jails.

As to the DNS issue, if your running correct DNS on pfSense, then all interfaces should be listening. So, point the DNS Server entry to whatever ip the freenas interface is on. Example, if your NAS is on a , than set dns to

You could also point it to,, etc… whatever you wanna use if not your pfSense box.

Make sure you check and reset the ip info on FreeNAS itself and the jails to be sure it’s all good.

It was not the jails I was having issue with. They seem to function fine which puzzles me. My issue is that the freenas smart notifications via email don’t work anymore. That is why I started pinging to see what was going on. My freenas emails have been set up and working for years with using SSL on port 465. That is where this thread started. I do appreciate the dns schooling. I will look into that however.

In your first reply, you stated that trying to ping failed. That’s a dns issue and if the email server can’t be resolved, it will fail.

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