Connection to smtp.office365.com timed out in Thunderbird

General system Applications
1

Hi,

I have my work e-mail set up in two computers: my personal laptop and my work desktop.
In both I use thunderbird and I have set it up to work my work e-mail. Everything worked fine until a couple of weeks ago, where on my desktop thunderbird refuses to send e-mail, issuing the following message:
The message could not be sent because the connection to Outgoing server (SMTP) smtp.office365.com timed out.

The weird thing is that on my laptop, which uses Arch, I have the exact same settings as on my dekstop using endeavouros, but it just works. Hence, I am sure that settings-wise I have everything correct, that from the server side, eveyrthing is correctly set up to work with e-mail clients, and I am just lost even in trying to debug the issue.

I have tried to delete the passwords and even the whole account on thunderbird with no success.

Any idea how to investigate this?

Thanks

2

Perhaps try:

ping -c 4 smtp.office365.com

Is there anything different about the way your two systems connect to the Internet? For example, is one using a VPN?

It seems you have probably done this, but do make sure the SMTP port matches too.

3

No VPN. At work I have both cable and wifi on the desktop, and I am usually on cable. I just tried with and without it, I get the same issue and in both cases I can ping the server:

11:36:34 âź© ping -c 4 smtp.office365.com
PING ZRH-efz.ms-acdc.office.com (40.99.201.210) 56(84) bytes of data.
64 bytes from 40.99.201.210: icmp_seq=1 ttl=240 time=1.41 ms
64 bytes from 40.99.201.210: icmp_seq=2 ttl=240 time=1.47 ms
64 bytes from 40.99.201.210: icmp_seq=3 ttl=240 time=1.42 ms
64 bytes from 40.99.201.210: icmp_seq=4 ttl=240 time=1.82 ms

--- ZRH-efz.ms-acdc.office.com ping statistics ---
4 packets transmitted, 4 received, 0% packet loss, time 3004ms
rtt min/avg/max/mdev = 1.410/1.529/1.819/0.168 ms

I don’t have my laptop here to check that the ping output is the same.

What do you mean by the ports match? In the Thunderbird settings? If so, they match.

4

Yeah, the Thunderbird SMTP settings was what I meant.

In Thunderbird, go through the process of adding a new account, but use the same username. It’ll hopefully auto config the settings and test. It’ll be interesting to see if that does, or doesn’t work.

5

I have specific instructions on how to set it manually from my IT department. Nevertheless, I have tried to remove my account and re-added it, asking for the automatic identification of the server. I also have removed the save password, so that it would trigger the 2FA.

By letting Thunderbird discover the server settings automatically, it gets them correctly, it prompts me for password and 2FA, but the problem persists: when I try to send an e-mail it times out the connection.

I have also tried to see whether there was some debug/verbose CLI option when launching Thunderbird, but I couldn’t find it. I was hoping to get some more info on this time-outs…

6

You could try launching Thunderbird from the command line and see if it provides some useful output there.

I hadn’t intended to suggest removing your existing account, I hope that hasn’t caused an issue for you.

7

No problem in removing the account and adding it back. I wouldn’t have done it if it was troublesome.

I tried to launch it from the CLI, but it provided no useful information.

8

maybe start with a complete new profile?

It happens with thunderbird profile get corrupted somehow

9

Yeah, that happened to mine, presenting as nuisance issues. It was at that point I transitioned to Betterbird instead.

10

Ok, today I brought my laptop to work as well, and I does not work either. So I though it was about the network, but if I connect to my phone as a hotspot it does not work for either the desktop and the laptop.

However, I may have updated thunderbird on my laptop just these days, and so it could be a problem with the new update.

Nevertheless, I tried betterbird, and it works, so I may just switch to that permanently.

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11

Actually, I just reinstalled Thunderbird 128 on my desktop, when opening it, it told me that my profile is incompatible with this older version, I created a new one, added my work e-mail and now it works.

By the way, I forgot to say it in my last message, I did try a new profile in the latest Thunderbird (version 136) and it didn’t work.

So it seems to be a problem related to Thunderbird.

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12

I’m also using Betterbird. Because the devs fixed things, devs from Thunderbird didn’t for a long time. Betterbird is not perfect but it works for me. :wink:

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