Advice for Apple Mail rules needed

Hi there, I’m currently trying to get some sanity into my emails and wanted to use rules to help me with some of the repeating stuff. I’m using Apple Mail with iCloud mail and currently have no plans for switching, so I would want to work with Apple Mail rules as best as possible.

So far I have tried some rules that would automatically move mails into certain subfolders (mailboxes I guess?). However what I have in mind does not seem to work?

Let’s take Amazon as an example: I receive multiple emails from Amazon - when I ordered, when package has been sent, when package will be delivered and so on. My idea was to first move all Amazon emails from the inbox to a subfolder/mailbox. Then with a second rule check if the received date is 3days or more and Mail is send/delivery notification move to Trash and just keep the order confirmation.

Problem seems to be, that the second rule never triggers and hence I have to manually delete those notification emails?! I think I read somewhere that each email only gets considered once by the Mail app and there is no „monitoring“ as with let’s say Hazel?

If my idea is not possible - same kind of handling idea goes for other emails as well, not just Amazon - do you have and ideas on how to achieve my goal/sanity with emails and rules :blush:?

Thank you so much in advance.

You are correct that youc an only run the apple mail rules once. The only way I can see to make your systme work is to have one rule that moves the order confirmation go into a single folder and then another that takes all the shipped, delivery etc ones into soemthing else and then periodically go i an by hand sort that by date and delete what you don’t want. It will take some careful crafting of the intial sorting rules to get them to work consistently.

I have had a problem recently in that my 100+ different Apple mail soritng rules got lost in the conversion from Catalina to Ventura. So my pro tip on creating rules is have each rule onky habdle a single type of email. Label the rules accurately (in your case I mihgt have rules Amazon-Order_Confirmation, Amazon-Order_Delivery_Info) and then be sure they are in alphabetical order in the rules pane. That makes it MUCH easier to find one that is misbehaving and edit it.

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Mail stops applying rules to a message when it encounters the Stop Evaluating Rules action, or when a message is transferred to another mailbox by rules used on a mail server or computer or device synced to your computer.

From Use rules to manage emails you receive in Mail on Mac – Apple Support (UK)

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I’m interested in this since I just got my renewal for Sanebox, and I’m not sure I’m getting the use out of it that warrants the price.

I’m wondering if you can combine Mail rules with Hazel. I’d have to go back and see how/if Hazel deals with mail.

To address my own suggestion, it doesn’t look like Hazel can act on mailboxes. Darn!

I use the smart mailboxes. You can see set very specific criteria and then move the emails in one go.

Actually smart mailboxes can be used as a saved search so you could save yourself the hassle of moving your emails around and just archive them.


Thank you for the recommendations and ideas so far. I’ll take the advice to better make more but simpler rules in order to hopefully be able to find out what’s working or not. And I take that Mail is fine with handling 100+ rules?

I also like the idea of maybe using smart mailboxes - at the moment I don’t use them at all …

Three more questions:

  • Am I correct that the rules sync across your Macs but they are deactivated by default?
  • What happens if I create a rule in iCloud online, would subsequent rules in the Mail app still run?
  • Am I correct that non of those features (rules, smart mailboxes) are available on iOS/iPadOS because the Mail app there is as dump simple as it gets?

Today I really feel I don’t understand the mail app. I tried to create some smart folders to dial down on some emails I can probably delete from time to time. Problem ist the Smart Folder doesn’t show the emails in question.

I started of doing a search from the little popover at the „from“ field which allows you to add them as contact, VIP or perform a search.
I did the search and got results as expected. I then copied the email address from the search field and put it into the Smart Folder rule: from is (or contains) email address. This gave no results. I tried to specify the mailbox that those emails are in but still empty. I tried a different email with a different email address and this time the Smart Folder worked as expected?

I came across several email addresses that did not show up in any Smart Folder combination. I tried to set a header field and even grabbed some fancy email address from the all header information of the email (something with random numbers and bounce) but that would also not trigger the Smart Folder.

Am I doing something wrong here? Does anyone have an idea why those emails refuse the Smart Folder rules?

Doesn’t answer your question directly, but I usually skip the ‘from’ field and just use the ‘entire message’ field. Works much better for me, unless I need something very granular or need complete accuracy, which is not usually the case