Deleting all email from Smart Mailbox

In Apple Mail v.16, I created a Smart Mailbox called, “Daily Delete” which contains all of the daily email crap (news, advertisements, notifications, etc.) that I don’t want/need to keep beyond today. When I go into this mailbox, select all, and delete, all of the email is removed from the mailbox as expected. However, it’s only removed for a few seconds, before it’s returned to the mailbox and not deleted. There are currently several hundred emails in the folder, which I can delete individually by hitting the delete key on my keyboard repeatedly, queuing up 100 emails for deletion. However, as mentioned above, selecting them all and hitting delete, which should work, only does so for a few seconds, before the mailbox is repopulated with the same email.

Any ideas on what’s going on, and why I can’t bulk delete them? I’ve been able to do this over the years with other mailboxes, but not this one.

Is it a Smart Mailbox? Can you exclude Trash in the Smart Search and see if that helps?

The Trash and Sent folders aren’t included in the mailbox, so it’s (hopefully) only looking at my Inbox(es).

A smart mailbox is not an actual mailbox. It’s just a saved set of search criteria. The messages still belong to the original mailboxes they came from.

I don’t use Apple Mail, so I don’t know what options you have, but if your delete operation doesn’t delete the original message from its original mailbox, then it is going to reappear the next time the smart mailbox updates itself. Just like how iTunes/Music Smart Playlists and Photos Smart Albums work.

With iTunes/Music, typing the delete key in a smart playlist temporarily deletes the track from the playlist, but the next time the playlist updates (whether automatically or manually), it will re-appear if it still meets the playlist’s search criteria. To delete the original track from your Library (getting rid of it from the app altogether), you can hold down Option while typing the delete key. Or locate it in the Library and delete it from there. The app will warn you about what you’re about to do, and after confirmation, it will delete the track.

Maybe you can try that with Mail? With any luck, the engineers developing Mail will follow the same convention, causing option-delete to delete the underlying message and not just remove the message from the smart folder.

Are those other mailboxes normal ones or smart ones? If they’re normal (not smart) mailboxes, then that would explain it.

If they are smart, then I don’t know why it isn’t working. Go take a look at each smart mailbox’s search criteria to see what the differences are. Hopefully the answer will present itself.

Yep, I know that the original emails aren’t being moved from their mailboxes. The “smart” mailboxes are just pointers/aliases to the original email.

The other mailboxes are “smart” as well. I have one called “WaPo & NYT”, which aggregates all of my emails from the Washington Post & New York Times in to one “smart” mailbox. I can easily select all of these emails, and delete them.

[You probably know this] Smart Mailboxes do not refresh automatically. I need to point to another mailbox and come back to the mart one to see any changes that have happened.

[New Stuff] However, even then, the updates for the last few items still haven’t taken. If I am very patient and wait several minutes, they finally seem to register. This seems to get a bit worse with every system update.

I use smart folders to delete mail once a year. Little bit foggy about how right now. Instead of hitting delete, try to select all and drag them to trash. I haven’t got my mac here just now, but I think there is a contextual menu (right click) that you can use also?

Yep, I’d tried dragging the emails to the Trash from the Smart Mailbox, but that didn’t work. I’ve just manually deleted all of the emails, but am mad curious why I couldn’t select all and delete.

I know when I do a search for old emails and do a full select and delete, they show up again, but are in the Trash Folder. There may be a way to not search in the trash. In Preference General there is a check box on the bottom on Searches. Do you have Trash selected there? What happens if you turn it off?

Yep, when I created the Smart Folder, I ensured that Trash and Sent were both unselected.

Not really the same issue, but tangentially, whenever I delete emails from my Trash folder (plain old Trash, not Smart Folder, and in Monterey it has become “All Trash”, but same issue) I always have to do it twice. They delete, but then reappear a second later. The second time they delete for good. This always happens, every time.

This hasn’t always been the case, only in macOS 11 and 12. Both with Intel and Apple Silicon. It’s not so big a deal I’ve ever tried to correct it; I’ve just accepted it’s yet another odd bug. I just thought I’d mention it because you never know if it’s a sign of some underlying bug that’s causing both symptoms.

Whoa. That’s really weird! Apple Mail has always had some really screwy issues.

In Mailbox > Edit Smart Mailbox, what are the specified conditions?

“Who am I going to believe, @Shamino or my own eyes?” Well, generally, @Shamino, but I’m at a loss to explain what I’m seeing.

I have a smart mailbox that shows anything that is unread and that Mail has placed in a Junk mailbox (in any of multiple accounts). When I select a message in the smart mailbox and delete it, it is gone from its original Junk mailbox and in the appropriate Trash mailbox. That’s what I want, and it seems to work.

More explicitly, the two smart mailbox rules are “Message is unread” and “Message is in mailbox All Junk”, with “Include messages from Trash” unchecked and “Include messages from Sent” unchecked.

Take a look at the settings on the Smart Mailbox…if it’s set to look at All Mailboxes then moving them to the trash doesn’t really change the All Mailboxes rule.

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Nothing out of the ordinary. I have many other rules similar to this, and they all seem to work, and I assume, allow deletion by selecting all.

A smart mailbox is a saved search, as I wrote.

What I don’t know (since I don’t use Mail), is what the delete operation does when applied to a message in a smart mailbox. If it is supposed to delete/move the message from its original folder, your observation sounds completely correct.

If the delete operation is supposed to work as it does in Music when applied to a smart playlist, then it would only remove the alias from the smart mailbox, but leave the original message in-place. Which would cause it to come back after the smart mailbox updates itself. But, again, since I don’t use this app, I have to rely on others to know how this operation is supposed to work.

Does it make any difference if you use Command-Delete (the shortcut for Edit > Delete) instead of just the Delete key?

To me, the odd thing is that the OP can apparently delete the messages individually but not en masse. If I understand the subsequent discussion of Smart Mailboxes (and if I didn’t miss anything), no one has addressed this disparity.

@TallTrees - I understand your frustration and am not sure how to address the Smart Folders deletion issue directly. I’ve tried using Smart Folders and basically gave up on them because A.) They never seem to follow standard email rules (as you have unfortunately experienced) and B.) They don’t sync across all of my devices (iOS devices don’t display Smart Folders).

Like you, I have a ton of stuff that I want to delete daily. Newsletters, bulletins, etc., that are informative but unworthy of keeping. I decided long ago to manage them by setting up aliases and filters in the iCloud Mail configuration. I have an address that’s and then a filter/rule set up to move all of those to a (real) folder that I have called Newsletters.

This offers several advantages:
• The mail is filtered according to the rule before it even reaches Mail on my devices.
• All mail addressed to that alias is available in the Newsletters folder on any of my devices.
• When I delete them from that folder, they are truly deleted.

I’m not trying to change your workflow and if you choose to continue using your Smart Mailbox, good luck. I’m just saying that my needs are similar and I’ve taken a different approach that seems to work really well when considering both Mail’s capabilities and limitations.