[MlMt] Enabling SMTP-Auth for Office365

Charlie Clark charlie at begeistert.org
Thu May 22 13:57:21 EDT 2025


Hiya,

I've recently had the fun of trying to get MailMate working with 
Office365 so that I have to use Outlook for Mac as little as possible 
– BusyCal does a good job with the calendar but can't show shared 
calendars, sigh. Benny has done a great job of getting things to work, 
but Microsoft does an even better way of breaking them and in my case, 
SMTP-Auth is disabled. :-(

If this is the case, the error message will at least point you to the 
right page for help:

https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission

But the page is both misleading and inaccurate. MailMate is registered 
for working with Office365 but SMTP-Auth has to be explicitly enabled. 
Luckily, I'm admin but unluckily, there is no option for users to enable 
SMTP-Auth for individual users. I suspect there is a global setting 
__somewhere__…

Fortunately, PowerShell for Mac is pretty easy to install and use. It 
has awful default colours so you will probably want to set up a special 
terminal profile with a dark background if you want to see what you're 
doing. After that install the relevant modules and then it's pretty easy

```
Set-CASMailbox -Identity 
charlie.clark at ifyoulikeitsomuchwhydontyoulivethere.com 
-SmtpClientAuthenticationDisabled $false
```

And, hey presto!

PowerShell is also great for setting mailbox delegation, especially if 
you **don't** want these added automatically to desktop clients. But 
basically, using Outlook and Exchange makes me want to cry. I've 
recently moved one mail account to OpenXchange (on mailbox.org) but I 
can't test the features that ~~losers~~ users will need most such as 
sharing and delegation.

Charlie

PS Benny, can you bump the maximum e-mail size so that we can send 
high-resolution screenshots more easily?

--
Charlie Clark
Sengelsweg 34
Düsseldorf
D- 40489
Tel: +49-203-746000
Mobile: +49-178-782-6226
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