SMTP Notifications not working anymore

tapufd

On the 18th of August, my ISP had an outage for several hours, and the problem was only fixed the next day.
Since then pfSense can't send out anymore SMTP Notifications.

This is the error message I get when doing a test:

Could not send the message to myemail@domain.something -- Error: Failed to connect to smtp.office365.com:587 [SMTP: Failed to connect socket: Operation timed out (code: -1, response: )]

I use Office 365 settings, and they worked fine.
In fact the same settings keep working in other tools.
I rebooted everything already of course (pfSense Plus VM, cable modem, ...) but nothing helps.
I did a "Test Port" on smtp.office365.com:587 and the reply is ok.

Any help on how to troubleshoot this further?
I'm stuck...

Br T

Gertjan

@tapufd said in SMTP Notifications not working anymore:

Any help on how to troubleshoot this further?

Ask pfSense ?
Do what pfSense does :
SSH into it (or console), option 8, and :

[23.05.1-RELEASE][root@pfSense.bhf.net]/root: telnet smtp.office365.com 587
Trying 2603:1026:c0a:1883::2...
Connected to ooc-g2.tm-4.office.com.
Escape character is '^]'.
220 PA7P264CA0437.outlook.office365.com Microsoft ESMTP MAIL Service ready at Thu, 31 Aug 2023 08:06:10 +0000

then type 'quit' to exit the connection.

edit :

This test shows several things.
I used a host name, aka "smtp.office365.com".
What really happens is : the host name is 'translated' into a usable IP address, like, in my case :

2603:1026:c0a:1883::2

This implies a very important step : DNS works ....

tapufd

I was reading some other community topics about slowness of Package Manager and Update, which I was also experiencing.
They were saying that via ipv4 it was quick but via ipv6 it was slow... tested it, and indeed, ipv4 quick, ipv6 slow.

My config was using DHCP for both ipv4 and ipv6 on the WAN interface, and I got for both an ip.
My LAN interface was only configured to use a static-ip for ipv4 and none for ipv6.
This config worked for many months/year(s).

I decided to disable ipv6 also on the WAN interface, and suddenly all is working fine again: Package Manager and Update quick again and my SMTP Notifications work again.

So my questin now: is this a bug on ipv6 or something?
Or was my orginal config with only ipv6 enabled on WAN, wrong in the first place?

Thx!
/J

Gertjan

@tapufd said in SMTP Notifications not working anymore:

I was reading some other community topics about slowness of Package Manager and Update, which I was also experiencing.

smtp.office365.com has a zillion local access points, so there is always one 'nearby' (Microsoft is a big company).
For me, all nearby IPv6 is working well.

If IPv6 is suspected, go Ipv4 mode :

telnet -4 smtp.office365.com 587

and test the other one also

telnet -6 smtp.office365.com 587

If you actually use IPv6 (have a working IPv6 connection).

edit : ah, ok, didn't saw your latest port.
Yeap, it is probably an IPv6 issue.
Where are you ? Where is - as far as you know - is the smtp.office365.com for you ?