dovecot - Apr 2021 - What imap ssl/auth settings work best with MS Outlook?

I repeatedly have a hell of a time getting clients' Outlook software 
working well with Dovecot. It's hard for me to test myself since I don't
have Outlook and it would be impossible to keep up with all the 
different versions anyway.

I've got the following settings, currently:

disable_plaintext_auth = yes
auth_username_format = %Ln
auth_mechanisms = plain login
ssl = yes

service imap-login {
#  inet_listener imap {
#    port = 143
#  }

  inet_listener imaps {
     port = 993
     ssl = yes
   }
}

service imap {
   client_limit = 1
}

It always seems to be hit or miss with outlook as to which encryption 
setting to use, which port to try, etc. With a recent client, I couldn't 
get them successfully logged in no matter what manual settings we tried. 
If someone can give me some tips on how to get most versions of Outlook 
cooperating well with Dovecot, I'd appreciate it.

On Wednesday, 28 April 2021 13:49:03 CDT Steve Dondley
wrote:
> I repeatedly have a hell of a time getting clients' Outlook software 
> working well with Dovecot. It's hard for me to test myself since I
don't
> have Outlook and it would be impossible to keep up with all the 
> different versions anyway.
> 
> [snip]
> 
> It always seems to be hit or miss with outlook as to which encryption 
> setting to use, which port to try, etc. With a recent client, I
couldn't
> get them successfully logged in no matter what manual settings we tried. 
> If someone can give me some tips on how to get most versions of Outlook 
> cooperating well with Dovecot, I'd appreciate it.
> 
Your best bet to make Outlook behave better as an IMAP client is to configure a
mail "profile" via
Control Pannel --> User Accounts --> Mail, and set all the particulars
there. Recent versions of Outlook have a stripped down configuration interface
that offers no flexibility. For example, from Outlook itself it's not
possible to set an IMAP login name that's not an email address.

-- 
Greg

On 2021-04-28 02:49 PM, Steve Dondley wrote:
> I repeatedly have a hell of a time getting clients' Outlook software
> working well with Dovecot. It's hard for me to test myself since I
> don't have Outlook and it would be impossible to keep up with all the
> different versions anyway.
> 
> I've got the following settings, currently:
> 
> disable_plaintext_auth = yes
> auth_username_format = %Ln
> auth_mechanisms = plain login
> ssl = yes
I think my problem might be here. Instead of %Ln, maybe I should have 
%L%n?

On 28 Apr 2021, at 12:49, Steve Dondley <s at dondley.com>
wrote:
> I repeatedly have a hell of a time getting clients' Outlook software
working well with Dovecot. It's hard for me to test myself since I don't
have Outlook and it would be impossible to keep up with all the different
versions anyway.
How old is the version of Outlook they are using? Office 2010 is a disaster, and
if I recall correctly 2014 has many issues as well.

Even so, it's terrible software that is designed to 'encourage'
users to use Exchange Servers for mail instead of real email servers.

-- 
Think of how stupid the average person is, and realize half of them
	are stupider than that.