What imap ssl/auth settings work best with MS Outlook?

[Steve Dondley]

On 2021-04-29 01:45 AM, @lbutlr wrote:
> 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.

I'm not sure. It's fairly recent though.

Some more nuttiness: I bit the bullet and downloaded a trial version of 
MS 365 and downloaded the Outlook desktop. On my mac, at least, there 
are two different interfaces/version of Outlook: the "old" Outlook and a 
"new," more minimalist version. You can switch between the versions 
easily.

On the "old" outlook, I was able to get things set up without issue. But 
with the "new" outlook, I couldn't send email or set up a new account.

It turns out I had to enable the smtp_tls_wrappermode setting to get it 
working with the "new" Outlook. See 
http://www.postfix.org/postconf.5.html#smtp_tls_wrappermode

I thought the wrapper setting was just for the long dead Outlook Express 
mail client. But now I'm wondering if I need this setting for some 
versions of Outlook.


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

I'm not conspiracy theorist, but I can't help but come to the same 
conclusion.

I am totally unfamiliar with Exchange servers. What do they offer, 
exactly, that dovecot/postfix does not (besides a revenue stream for 
MS)?