Newly emerged Microsoft / Apple Mail conflict

You’ll probably want to acquire some local IT help for maintenance and archiving, and for explaining.

Microsoft is moving to more modern connection authentication for their mail servers.

Apple and various other mail providers have also moved to more modern authentication for mail.

Here is the Microsoft statement:

https://support.microsoft.com/en-us/office/modern-authentication-methods-now-needed-to-continue-syncing-outlook-email-in-non-microsoft-email-apps-c5d65390-9676-4763-b41f-d7986499a90d

Basically, Microsoft are requiring better security for mail.

This authentication change will not disallow access from the Apple Mail app, nor from other recent mail clients.

To upgrade to the newer mail connection security, remove the Microsoft mail account from Apple Mail app, and re-add it.

This remove-and-add will not affect mail on the server, and will not affect mail stored on the client.

Per the linked Microsoft article: “Apple Mail supports Modern Authentication by default when you setup the account as Outlook.com”. Steps for migrating common mail clients re included, too.

If you want to migrate your mail to another mail provider or hosting provider, a tool such as imapsync can be useful for migrating mail to a different mail server, though simply downloading messages to a working mail client and then re-uploading to another mail server or archiving locally is probably the easiest and most common choice.

Paying for mail hosting is one way to get better support than is available from free services, if that is of interest. Free hosting services don’t have support. Not past the usually-limited value of scraping your data, that is.

I would most definitely and emphatically not suggest running your own mail server.

As for archiving your important data, that’s a whole ‘nother topic. And a large and ever-changing topic.

Here’s an older US Library of Congress government website with an intro to that topic: https://www.digitalpreservation.gov/personalarchiving/

Mail is not where I’d store any important information you want or need other folks to find, having assisted somebody with this. Wading through ads and spam and newsletters and the rest of the ephemeral detritus of life with email — looking for unknown nuggets or for important info — just isn’t going to happen, or it’s going to be rushed at best. (Not unless you’re a particularly notable person, or archiving your correspondence is legally required, that is.) As I’ve told more than a few folks running businesses and organizations, mail is where you bury your important organizational information. Mail is not where you preserve it.

More generally for Apple services, if you have not set up Recovery Contact and a Legacy Contact, go start there.

[been pondering whether to post some videos on these and related topics, but that’s all fodder for another discussion.]

anne1111 wrote:

Hi all,

I've found a solution that worked for me (see wlow)and posted my response on a more general thread on the topic

New protocols for using Apple Mail with H… - Apple Community

Thanks again for all of the thoughts and approaches here already!

The solution is to remove and re-add the email account.

That creates a connection using the currently-available connection security.

Any “conflict” here is patently false.

“To upgrade to the newer mail connection security, remove the Microsoft mail account from Apple Mail app, and re-add it.

This remove-and-add will not affect mail on the server, and will not affect mail stored on the client.“

Okay, so how do you do that? I mean, very detailed step-by-step for iPhone and iPad. My main email account is hotmail and I need to access it. I have no freakin idea how to do this stuff.

Princess Bob wrote:

Okay, so how do you do that? I mean, very detailed step-by-step for iPhone and iPad. My main email account is hotmail and I need to access it. I have no freakin idea how to do this stuff.

Here is how to: Add and remove email accounts on iPhone - Apple Support

Here is how to: Add and remove email accounts on iPad - Apple Support

Here are the official Microsoft directions: https://support.microsoft.com/en-us/office/modern-authentication-methods-now-needed-to-continue-syncing-outlook-email-in-non-microsoft-email-apps-c5d65390-9676-4763-b41f-d7986499a90d

You will need the credentials to your Microsoft account.

Whatever conflict may exist with your Mac and some Microsoft service is not clear to me, but what is clear is that Microsoft wants to compel everyone to use their products. In the case of Microsoft email services in particular, they always have had their own non-standard way of doing things. That means Microsoft Outlook and the rest of their "office" products, for which they will want money in exchange for the elite privilege of using them.

Earlier this year I went to the trouble of migrating ALL my emails (sent and received) to the "On My Mac" folder in Apple Mail, with subfolders mirrored from the server-stored system I had.

If you want to preserve email messages, that's the way to do it. Otherwise they will be forever held hostage by whatever servers host those messages, which could conceivably be made irretrievable, inaccessible, or simply lost at their whim. They won't care. No one will care about your email messages but you. Leave them to fight their Titanic battles among themselves. You don't have to participate.

Personally, I delete old emails.

I keep all receipts downloaded into a folder on my Mac. Same with other attachments.

You don’t need to feel obligated to anything or anyone.

When you delete, you take the power away from them, keeping you in control of your digital life.

Take care! 👋🏼😉

I completely understand and agree with your concerns. Overreliance on any one particular technology or service is the antithesis of a robust system. The systems we have grown to rely upon today are incredibly fragile. All you can do is prepare for its collapse: be autonomous, to whatever practicable extent you can.

It's a bit off topic but Crowdstrike Falcon is nothing compared to what could happen. I got an email yesterday from one of my clients expressing appreciation for the fact I recommended that they do not use that particular Microsoft service. They avoided what would have likely been a multi-million dollar bitter pill to swallow. The so-called experts who characterized its failure as "ironic" completely miss the mark. It's not ironic for anything — whether it's an intentional coordinated attack or a pervasive, near-universally installed system intended to prevent such an attack — to result in the exact same outcomes.