Exchange Online Basic Auth Deprecation

We’ve been hit by MIcrosoft disabling basic authentication for their Exchange service. I’m aware this is a well intentioned security issue and I’d love for all of our old machines to be replaced to accommodate the new requirements but sadly this isn’t going to happen any time soon.

We’re stuck in a position where most of our users can’t log in to their email service. Post Mojave systems are OK but we have several older.

Interestingly, Apple says Mojave is the earliest system which uses Modern Authentication BUT we have one Sierra system which works fine whilst other Sierra systems don’t. Can anyone submit why this Sierra system might be working or how I could make the others work?

We have the option of using and webmail but the users are screaming they want their mail clients to work.

I’m sorry to hear that this is inconveniencing you. IMO it’s an unfair and unnecessary imposition by Micros~1. I don’t share the enthusiasm for OAUTH2, which I frankly consider to be a racket that mostly benefits the service operator. I’m glad Apple never implemented it (they have their own “Apple Token”, but only for their own client apps for single sign-on).

On the face of it you’ll have to explore using a client proxy that turns traditional authentication into OAUTH2. Something like this. Needless to say, you’ll probably need to hold hands, if you aren’t needing hand-holding yourself.

I’ve updated a few machines to Mojave and they’re now fine. We’re buying a few new Mac Minis (we’ve been waiting patiently for the M2 version) so that will resolve a few more.

The puzzle for me is still why some older machines are still working. We’ve found a couple of Sierra machines and even one Yosemite machine which seems to be managing just fine. We have one machine which has three accounts and two of them work and one doesn’t.

Finally, Outlook sucks rocks (IMHO).