> On 22.05.2025 at 17:47 Paulo Pinto via mailop wrote:
>
> 
> Well ... because TLS "may" as in it is not mandatory and the plain text 
> fallback is still (even today) a valid (user choice ) reality ?
>
> When we reach the stage of "no plain text communication is acceptable" that 
> would be OK. As we are today it is not.
> It's unsecure ? Obviously. Is it still accepted as per RFC? Yeap, so deal 
> with it.
>
> Follow the standards and stuff will fall into its correct bucket. It's not 
> that hard ( well, unless it's M$ ... )

There is RFC8314 which recommends to use TLS instead of cleartext connections 
(with or without STARTTLS upgrade). I have not encountered an email service 
provider that offered email submission or mailbox access without TLS in the 
last couple of years.
Trying to access mailboxes via IMAP on port 143 is similar to browsing the web 
on port 80: You won‘t get very far.

I cannot tell whether the issue with proxied Outlook connections is caused by 
TLS, as I don’t use that service for obvious reasons. However in case the 
connection fails because the client side supports only TLS secured connections 
and the server side on the other hand supports only cleartext or STARTTLS 
connections, then there is not much discussion about which side must adapt.

—
BR Oliver

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