Update on Apple Mail issue

leftcoaster wrote:

I've been working with an Apple rep for a couple of months now about a recent change in behavior with my Apple Mail app and wanted to post an update.

With a recent upgrade, Apple Mail no longer prompts with a previously used folder when I click on an email with a recognized sender and/or choose the Move drop menu. This previously worked fine on my laptop but then stopped; it continued to work fine on my iPhone.

Try the Drag & Drop is the go to way...

Mail User Guide for Mac - Apple Support

You can submit your user feedback directly to the product team—

you can submit your Apple Feedback: https://www.apple.com/feedback/mail.html

leftcoaster wrote:

With a recent upgrade, Apple Mail no longer prompts with a previously used folder when I click on an email with a recognized sender and/or choose the Move drop menu. This previously worked fine on my laptop but then stopped; it continued to work fine on my iPhone. I tried a number of suggestions, including re-setting up the email accounts (more later on this) and THREE complete and erase and installs of Monterey ... The latest wrinkle is that I had to delete and re-install the Gmail account on my iPhone and now it no longer prompts with a previously used folder as well.

I don't see that issue on Monterey -- I think it works properly for most users. The question is, what is unique to your setup that might have led to this.

(An aside: deleting and reinstalling the account on the iPhone probably removed the history information as well that enables that prompting for the folder. I agree with you, it is nice to have this feature.)

You might try several things (these are all easy and non-intrusive to try):

Boot into Safe Mode. My guess is that Apple already suggested this, but if not it's worth a try. Safe Mode removes caches, which might have some of the faulty "history" that is needed for this feature to work.

Boot into Recovery and then run Disk Utility and have it repair the disk. In principle, this is already done when you boot into Safe Mode, except from Disk Utility you can see the messages and whether it worked or not.

Create a new user, then see if Mail behaves properly under that user. If it does, then that narrows the cause of the issue to something specific to your original account/user.

Run Etrecheck and post the results here using the Additional Text button below. This works best if you grant Etrecheck full access to your entire Mac and disk. You can unguent that after it completes. Etrecheck provides anonymous information about your setup and what is installed. There is an off chance that some old installation or software is causing the misbehaviors you are observing.

The phone may be a separate (possibly related) issue, perhaps post that question in the iPhone Discussions area.

Moving everything to the "new" account is doable but depending on the complexity of what you have installed, might be easy or a bit of a hassle. If ALL your email is there on the "new" account (that would be the case if you are using Exchange, GMAIL, IMAP and don't have "On My Mac" stored emails; but you should check that first), and you don't have complex installations under your "old" account, that migration might be simple. You will have to take some care to move over all your bookmarks and favorites and the like from your browsers. If you have something like Adobe CC installed, it might be available for all users on the Mac, but any presets/settings would need to be shifted to the "new" user.

Have you tried using Mail in safe mode on the original account? If it works right, then it is definitely else that is installed under the "old" account, Etrecheck might suss it out. In fact the fact that it works under the "new" account means something installed (or some setting) under the "old" account is causing this. Again, Etrecheck might help here.