Office 365 - Legacy Applications That Don't Support SMTP over TLS

[FN-GM]

Hello,

 

We use Office 365. We have a full blown Exchange server here that is delivering emails for a single legacy application. The said application doesn't support TLS so we can't use the Exchange Online SMTP relay.

 

I was looking at Stunnel. This could be installed on premise, accept messages that are not secure and forward them on to the Office 365 relay via TLS.

 

Does anyone else have any other possible solutions please?

 

Thanks

[free780]

Bring the mailboxes back on prem. Yes you've still got IMAP/Pop3 traffic within your network. In October MS will stop legacy authentication apart from SMTP to Office 365.

[CHiLL]

Have you looked at using Windows Server's SMTP server feature? I have it configured on one of our servers, though both it and the Office 365 relay are both configured with TLS. I haven't tried it with the on-site relay without TLS.

[andy_b]

We have a small Ubuntu VM running postfix for such things.

[FN-GM]

Yes you've still got IMAP/Pop3 traffic within your network.

 

No we don't

[free780]

No we don't

Sorry I meant in the context of this announcement.

 

https://techcommunity.microsoft.com/t5/surface-hub/basic-authentication-retirement-for-legacy-protocols-in-exchange/m-p/871839