Outlook autodiscovery

[daychilde]

SYSTEM INFORMATION
OS type and version	Ubuntu 22.04.5
Virtualmin version	2.202

I’m finding some old topics but nothing that seems to apply to this issue. There was a topic from 2020 where someone worked on this, but basically I’m trying to ask if there’s something I’ve missed somewhere on my setup.

I’m new to Virtualmin, but I’ve been a cPanel user since around 2002 and had my own dedicated since 2004. So I’m a newbie in some ways, but been around a little in others.

So the issue is I’ve spun up a new server. I’ve created an email account on a domain that points to the server - a propagation checker website confirms that everyone should be seeing the domain pointing to the server. And locally it all points to the new server (ping, website loading with new content added on new server).

When I try to add the email to Outlook 365 (the Desktop Outlook application), it prompts for the password, then says it has to sync, and then fails. Manually changing the config isn’t seeming to work.

I can absolutely verify that I am using the password I’ve set up.

I am using the full@email.address for the one I created; I also tried adding the main user which says it has email setup (by default) and I did notice the username was just the username, so I did update that when I tried to add that one.

Is this a known issue? And for IMAP, what are the preferred settings for a manual setup to make Outlook happy?

Now that I’ve asked my question, I just want to say that as cPanel kept raising its prices, I spun up a server last year and tested another panel and… it was good, but not good enough. As I was looking around for options again with this price increase, Virtualmin kept popping up as a suggestion, so I thought I’d give it a go.

WOW.

So far, I am so incredibly impressed. So many things I’ve WANTED in a panel that are there. I love love love it so so much. So many options I longed for that are included!

And a tiny breath of fresh air that you’re using Discourse for your forum, which also makes me happy because as a long-time redditor, I’m a sucker for markdown.

Anyway, thank you for letting me express exuberance while I ask my question.

[jimr1]

Have a look at the mail server logs & see what is happening at the time outlook tries to connect, there are various ways of doing this you can use

1. webmin->system->system logs & select the correct service to monitor (postfix@-.service)
2. webmin->system->system logs RS and choose mail.log
3. from the command line in a terminal tail -f /var/log/mail.log or
   journalctl -u postfix@-.service -f --no-hostname
   and post the data back here if you don’t see an immediate error, if you do that please just post the relevant sections of the output & not the whole output

[daychilde]

Thank you most kindly for the reply.

Well, the good news is that my created mailbox is now working - I had to go try to connect again since I now have time to look at this again. And it worked. So perhaps just a matter of propagation or something.

Still can’t connect to the account - using user@domain or just user, though. I reset the admin password just to make sure it was correct.

When I look at the postfix@ log mentioned, I don’t see my IP address listed, and I definitely - based on timestamps - am seeing new activity, although not so fast that the last 100 lines isn’t enough, it’s about the last couple of hours, and I refreshed after I connected.

Oddly, I still don’t see my IP address after the successful addition of the createduser@domain, so I’m thinking that maybe Outlook must connect from its servers or something.

So I’m looking at lines like this:

Nov 16 01:36:04 one.nullusanxie tas. com postfix/smtpd[1342884]: connect from unknown[141.98.10.83]
Nov 16 01:36:07 one.nullusan xietas .com postfix/smtpd[1342884]: warning: unknown[141.98.10.83]: SASL LOGIN authentication failed: authentication failure
Nov 16 01:36:07 one.nullusan xietas. com postfix/smtpd[1342884]: lost connection after AUTH from unknown[141.98.10.83]
Nov 16 01:36:07 one.nullusan xietas. com postfix/smtpd[1342884]: disconnect from unknown[141.98.10.83] ehlo=1 auth=0/1 commands=1/2
Nov 16 01:37:21 one.nullusa nxietas. com postfix/smtpd[1341898]: lost connection after EHLO from unknown[52.125.136.4]
Nov 16 01:37:21 one.nullusanxi etas. com postfix/smtpd[1341898]: disconnect from unknown[52.125.136.4] ehlo=1 commands=1
Nov 16 01:37:25 one.nullusanxi etas. com postfix/smtpd[1341685]: connect from unknown[52.125.136.4]
Nov 16 01:37:44 one.nullusanxi etas .com postfix/smtpd[1341685]: lost connection after EHLO from unknown[52.125.136.4]
Nov 16 01:37:44 one.nullusanxi etas. com postfix/smtpd[1341685]: disconnect from unknown[52.125.136.4] ehlo=1 commands=1
Nov 16 01:39:02 one.nullusanx ietas. com postfix/anvil[1340651]: statistics: max connection rate 5/60s for (smtps:52.125.136.6) at Nov 16 01:33:19
Nov 16 01:39:02 one.nullusanx ietas.com postfix/anvil[1340651]: statistics: max connection count 4 for (smtps:52.125.136.6) at Nov 16 01:33:19
Nov 16 01:39:02 one.nullusanxi etas. com postfix/anvil[1340651]: statistics: max cache size 6 at Nov 16 01:32:33
Nov 16 01:39:33 one.nullusanxi etas. com postfix/smtpd[1343963]: connect from unknown[141.98.10.83]
Nov 16 01:39:37 one.nullusan xietas. com postfix/smtpd[1343963]: warning: unknown[141.98.10.83]: SASL LOGIN authentication failed: authentication failure
Nov 16 01:39:37 one.nullusanx ietas. com postfix/smtpd[1343963]: lost connection after AUTH from unknown[141.98.10.83]
Nov 16 01:39:37 one.nullusan xietas. com postfix/smtpd[1343963]: disconnect from unknown[141.98.10.83] ehlo=1 auth=0/1 commands=1/2

That should cover the timeframe I was connecting, I think. But none of that is my IP. And I can’t tell the user that it was trying to connect as…

I’d love your advice on how to proceed from here.

I can verify that my virtual server user has, accoridng to the user edit page, email access along with the others - Database, email, SSH, and FTP access. So in theory it should work, I’d think.

Thank you for your patience with me

preposting edit: oof, I understand the link policy, but I just had to go through the logs and break up the “link” that I didn’t really want to linkify anyway. meh. lol. Good for spam, pain for pasting. lol

[jimr1]

try connecting through usermin (which uses port 20000, unlike webmin on port 10000) and see if you can log in correctly with all users, you also can auto login to usermin as any user from virtualmin → edit users → user

[stefan1959]

Failed connections can cause a block in fail2ban so beware of that.

Add your IP in the ignoreip list so it won’t get banned.

[ID10T]

@daychilde

And for IMAP, what are the preferred settings for a manual setup to make Outlook happy?

I wish they would put the ‘show email client settings’ in usermin.

This will put a block on an address until removed or the firewall is restarted. It will help clean up the logs when looking.

firewall-cmd --add-rich-rule="rule family='ipv4' source address='52.125.136.0/24' drop"

Looks like this was finally added to the interface. Thanks @Ilia ?

Have you checked to make sure autodiscover is in you DNS record? I think it is an option you have to choose during setup.

[Ilia]

@ID10T

Have you checked to make sure autodiscover is in you DNS record? I think it is an option you have to choose during setup.

This can be enabled on the “Email Settings ⇾ Mail Client Configuration” page.

[daychilde]

Sorry it’s taken me a while to get back here, I have been dealing with health issues. Whee.

So I realized something: There is no option in the latest Outlook to change the IMAP username.

You can change the SMTP username, which is what I was doing. (Didn’t notice that subtlety until today)

But Microsoft forces you to use the email address for the username for some inane reason, with no option to change that even in advanced/manual setup.

Here’s an article I found on it: Redirecting

So this is an unsolveable issue for this email client, which is incredibly frustrating. I’ve been a Windows geek since 3.1 days. I’ve used Outlook since 1997.

But I can’t use it for this email account, for NO GOOD REASON AT ALL.

I suppose I can forward email to another email account that will use user@domain-style username.

How stupid.

Thank you all for the support.

No thank you to Microsoft on this one.

[stefan1959]

Just to be clear, this is the free Outlook app (new), the paid Outlook versions should edit fine or am I wrong there?

[daychilde]

Paid Outlook Windows application. In the past few months they were pushing folks to the latest “new” version - but this is the standalone app, which is part of the office 365 home subscription I have.

Can post screenshots if wanted.

[stefan1959]

Paid version is call Outlook or Oulook Classic app, I think your using the free one that is a bit limited.
In search do you see 2 versions on your PC.
“Outlook new” is the replacement for the Windows 10 / 11 Mail

https://answers.microsoft.com/en-us/outlook_com/forum/all/new-outlook-vs-outlook-in-microsoft-365/e367b524-b637-49ac-8405-3d801af343c1

What version of Outlook do I have? - Microsoft Support

[daychilde]

Whatever you want to call them, I can run both, and neither allows me to change the IMAP username.

To be clear, this is a frustration with Microsoft, not Virtualmin.

[stefan1959]

on the page there is a video on how to change, about a minute in you will see email address is editable

Change or update email account settings in Outlook for Windows - Microsoft...