Why does Apple make it impossible to apply rules to sent mail?

Why does Apple deliberately make it impossible to automatically apply rules to sent mail in Mail.app?

Posted on Apr 11, 2025 3:11 AM

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Apr 13, 2025 7:50 AM in response to 100 Watt Walrus

100 Watt Walrus wrote:

That's exactly the problem. It makes no sense to have rules, but have them apply only to the inbox. I shouldn't have to manually drag around every single message I send. I want all mail related to Project X to go in the Project X mailbox — not just incoming Project X mail. But for some reason, Apple hasn't bothered to make that possible, even though rules for sent mail have been a common feature of email apps for 30 years.

I'm just wondering if there's some reason I don't know about that Apple thinks this is OK.

Maybe I'm just not understanding your issue and I'm sorry for that. Smart Mailboxes might be what you can use:: Use Smart Mailboxes in Mail on Mac - Apple Support (MD)

I use several email apps and have done so for decades in a project oriented environment and I have never run into the issue you are describing. What email client does what you need? Why not just use that email client?


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Apr 11, 2025 6:56 AM in response to 100 Watt Walrus

100 Watt Walrus wrote:

Why does Apple deliberately make it impossible to automatically apply rules to sent mail in Mail.app?

Not sure what it is you are trying to accomplish. Rules are applied to email as they arrive to the inbox not to the outbox. Please provide more details and context regarding what it is you want to do.

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Apr 13, 2025 3:34 AM in response to BobTheFisherman

That's exactly the problem. It makes no sense to have rules, but have them apply only to the inbox. I shouldn't have to manually drag around every single message I send. I want all mail related to Project X to go in the Project X mailbox — not just incoming Project X mail. But for some reason, Apple hasn't bothered to make that possible, even though rules for sent mail have been a common feature of email apps for 30 years.


I'm just wondering if there's some reason I don't know about that Apple thinks this is OK.

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Apr 14, 2025 9:21 PM in response to BobTheFisherman

There are literally no good email clients for Mac. Every single one has insurmountable shortcomings, so I'm always trying to panel-beat one or another into a shape that makes them do any of the things I really need. At the moment, I'm so frustrated with the others in my rotation, that I'm back to Mail.app, hoping to find workarounds for its myriad shortcomings. So that's why I'm not using another client...at the moment.


Smart mailboxes are OK, but there's no way to group them or collapse those groups. If I were going to use them for everything Mail's filters fail to do properly, I'd have dozens of them.


In this case, I want any mail I've sent containing "Project X" to be automatically files in my Project X mailbox. It's absurd that I can make a filter routing all incoming "Project X" mail to that mailbox, but if I want all my sent "Project X" mail in that mailbox, I have to drag it there myself.


Postbox could filter sent mail — Postbox could to everything — but it's abandonware. eM Client can filter sent mail, but it's buggy. Thunderbird-based apps can filter sent mail, but are otherwise awful. I think the Pro version of Canary can too, but it's riddled with other dealbreakers. There are others (I'd have to check my extensive notes comparing apps), but again, dealbreakers.


I genuinely don't understand how anyone can work with all their Sent mail chucked into one Sent box unless they move every single message by hand. But I guess I'm in the minority — and I guess I'm just out of luck.


Thanks for trying to help.

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Apr 15, 2025 6:34 AM in response to 100 Watt Walrus

100 Watt Walrus wrote:

There are literally no good email clients for Mac. Every single one has insurmountable shortcomings,

No offense intended at all but, if no email client ever meets your needs, it's likely that your needs are not typical.


Notion has a new email client. I haven't played with it much as I'm very happy with Readdle's Spark. But it's new enough that you may not have tried it yet.

I genuinely don't understand how anyone can work with all their Sent mail chucked into one Sent box unless they move every single message by hand.

I search my sent box if I need something. My goal is to avoid saving emails in most cases, though.

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Apr 17, 2025 1:39 AM in response to IdrisSeabright

Thanks for the NotionMail tip. That was not on my radar. Although it looks like it's more an email service than an email app. There's no download that I can see, just a login/create account.


My needs probably are atypical, but I'd suggest that has a lot to do with people not knowing what they're missing. For example, once you've experienced keyboard navigation and keyboard filing, it's pretty hard to give them up. The time and hassle they save is exponential.


As for the sent-box thing, I want conversations to stay together, 100% of the time. Every part of a conversation should be in the same mailbox. I shouldn't have to search my sent box for a particular email. It should be right there with the rest of the thread. If for no other reason than to save time having to search. :)

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Apr 17, 2025 7:09 AM in response to 100 Watt Walrus

Just a shot in the dark and a guess, sorry.

What if you sent the email to yourself (BCC) when you sent out an email containing the keywords needed to activate the rule you wish to run?

So if you send an email with "Project X" to someone and include yourself in the BCC address field would the rule for incoming email work?

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Apr 17, 2025 7:12 AM in response to 100 Watt Walrus

100 Watt Walrus wrote:

Thanks for the NotionMail tip. That was not on my radar. Although it looks like it's more an email service than an email app. There's no download that I can see, just a login/create account.

There is a download. The button is at the bottom right corner of the web interface. One caveat, I technically have a paid Notion subscription (it's actually free because I work for a university). It's possible that's required but I don't know.

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Why does Apple make it impossible to apply rules to sent mail?

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