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

[Tim Dickson]

On 29/04/2021 10:22, Steve Dondley wrote:
> 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)?
>
built in calander integration.

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