Can't reply or forward email in Outlook

  • Just to qualify this, I'm new to pfsense and running 1.2.3. I have it working well with a static WAN address and DHCP on LAN. Port forwarding is working fine. The issue is that with Outlook when replying or forwarding messages that have a web link in the body, they are returned to me with the error that the email address is unreachable. I have read on a couple other topics where this is a known issue and no one seems to have the solution. Does anyone else have an idea why this is happening? I use port 465 SSL for outgoing and 110 for incoming. I have tried creating rules for that port but no luck.
    thank you,

  • Doesn't sound like anything pfSense could be responsible for, particularly if it works with other emails. You should instead look at the mail server you're using and check it's logs.

  • I should also add that I only seem to have this problem when I trade email with a location that is also using a pfsense firewall. It is displaying the same issues as mine is. It receives email no problem but it won't reply or forward on either end. I'm not sure where to look for the logs on my hosting services (aplus net) web site but I may not be able to. The other pfsense firewall is using godaddy for email hosting. When I remove my signature (which contains a link to my web site) I can reply and forward with no problem. Very strange.

  • Rebel Alliance Developer Netgate

    Do you both have snort enabled with blocking? Perhaps you're tripping some kind of alert in snort. Could also be an MTU issue if you're seeing it with attachments, though that isn't quite as common.

    Check the firewall logs, any package logs you have enabled (snort, squid, etc) do a packet capture on the LAN side and WAN side of the attempted e-mail transaction, it could be pretty much anything. Though I can't say I've never heard of that particular issue.

  • Thank you Cry Havoc and Gimp. I don't know why but email is working fine now. I wish I knew why that ws happening but I can't even reproduce it to try checking things. I guess it's just one of those "ghost in the machine" things. Thanks again!!

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