> On 18.07.2023 at 16:21 Benoit Panizzon wrote:
>
>> As far as I know Microsoft never officially supported or advertised STARTTLS 
>> for its mail submission services. Given that RFC8314 "Use of Transport Layer 
>> Security for Email Submission and Access" basically deprecates STARTTLS in 
>> favor of implicit TLS for submission services, I wouldn't expect that 
>> STARTTLS is coming back if it's currently broken.
>> Maybe Michael Wise can shed some more light on this.
>
> They definitely advertise STARTTLS as a supported CAPABILITY, check
> yourself:

By „advertised“ I was referring to the documentation, where STARTTLS support is 
not mentioned.
Their IMAP service on the server is obviously broken, I just have low hopes for 
the mentioned reasons that STARTTLS support is going to be restored.


> Weird... if somebody could point me to what I'm doing wrong...
>
> Our Postfix:
>
> Jul 18 08:04:53 asterix postfix/smtp[81902]: Untrusted TLS connection 
> established to hotmail-com.olc.protection.outlook.com[104.47.51.33]:25: 
> TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
>
> Is very capable to STARTTLS with Microsoft...
>
> So trying again:
>
> $ openssl s_client -starttls smtp -connect 
> hotmail-com.olc.protection.outlook.com:25
> [cert validation stuff]
> 250 SMTPUTF8
> ehlo example.com
> rset
> quit
>
> => Nothing!

I think you’re mixing up MTA to MTA connections and email submission.

If you want to deliver messages to hotmail.com for local recipients:
hotmail-com.olc.protection.outlook.com:25 with optional STARTTLS

If you want to submit emails from a MUA:
smtp-mail.outlook.com:587 with mandatory STARTTLS

If you want to fetch emails via IMAP:
outlook.office365.com:993 with implicit TLS

You cannot interchange those hostnames or ports.

—
BR Oliver

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