Can AppleScript provide my desired functionality (as described) to Mac Mail?

I would like to be able to shutdown my last Windows 10 computer and go 100% Mac - but there are a couple of email functions I rely on that only seem to work in Outlook on Windows that I can't seem to do in Mac Mail. Since I have a Microsoft 365 subscription I have tried Outlook for Mac, but it doesn't even come close to being useful (either the feature starved NEW version or the Classic version).


I have no AppleScript experience, but am prepared to tackle the learning curve it if I can get some positive encouragement that it won't be a waste of time. Hence the question: Can AppleScript provide my desired functionality (described below) to Mac Mail? If AppleScript can't do it then there is no sense in wasting a lot of time trying to learn how to use it.


First Problem - with Mac Mail Forwarding Rules and Functionality:

I use a dedicated Gmail account and Outlook for Windows rules to filter for a private chat group before they are passed to a cloud based email list server. The list service is restricted to non-commercial uses, like our group of ~50 friends. This email list service is fully automated, reliable and cheap, but limits the size of attachments to keep operating costs down. To get around this, all our new thread messages are sent to the Gmail account I set up for this purpose. An Outlook rule forwards smaller messages (smaller than the maximum size limit) directly to our email address on the list server. Further conversation (generally always simple text replies) continues on the list server. This works because any replies back to the group remove the original attachments and so far nobody has ever replied back with an oversized attachment. A second Outlook rule forwards larger messages (over the maximum size limit) directly to each of the same group of ~50 members. My problem is duplicating the following functionality that is not available in Mac Mail:

    1. The large emails forwarded directly to group members by Outlook are sent without exposing the full list of addresses. As if the addresses were placed in the BCC: list instead of the To: list.
    2. The large emails forwarded directly to group members also set the Reply To: address to our list server address , where all subsequent email conversation is exchanged. Note that setting the Reply To: address is done as a global setting for the dedicated email account and not as part of an Outlook rule.


2nd Problem - Editing the Subject line in Received Message Prior to Filing:

I use a heirarcical folder structure in my primary Email account to file messages I want to retain. To simplify retrieval later, I frequently change the Subject: of received messages prior to filing. Outlook on Windows allows me to edit a message for both subject line and body content. Mac Mail does not support editing for any messages that are not new messages been sent or received messages being forwarded. A Mac Mail suggestion in a Forum was to start forwarding the message, edit the Subject: then exit and save the message as a Draft. The Draft message with the modified subject line can then be dragged to the intended folder for filing. This works for the subject line but the original From: address is lost and replaced by my address as though I had actually forwarded it.


So, any opinions would be appreciated about whether these two functional requirements could be implemented with Applescripts from Mac Mail rules or some other invocation mechanism

MacBook Pro 16″, macOS 14.1

Posted on Dec 3, 2023 12:54 PM

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2 replies

Dec 3, 2023 1:59 PM in response to BobzMac

AppleScript is not an appropriate choice for pretty much anything that doesn’t involve directly scripting GUI apps. And I’d not really want to have to GUI-script anything close to the complexity likely involved here.

The first requirement is seemingly writing your own custom front-end list server for an existing list server. If the gmail rules can’t filter this with your existing design using gmail as an intermediary, then you are probably going to be scripting an IMAP server.


The second is scripting the mail store, and trying to use mail as a database. Apple Mail isn’t inclined to allow user’s messages ro be modified. Your own mail store could do that, or forwarding the message with a different subject as was referenced.


In aggregate, you’re seemingly incrementally backing your way toward creating a customer relationship management (CRM) system, or toward a list server that you yourself are running. The latter could be hosted in your own instance somewhere. Downside of running mailing list servers (particularly running those locally) is dealing with bounces, and getting reported for spam, or getting reported for illegal content.


One of the “write me an app” services around the ‘net might be a possible approach here too, though you’ll want to work on the specification for what you want before soliciting bids. Or keep running tools such as Outlook that are better suited for your requirements, obviously. Or hosting your own list server.

Dec 3, 2023 2:19 PM in response to MrHoffman

This is a really good answer and exactly the kind of information I was looking for. Running a list server is not a viable solution for me. I know all about the bounce, spam and copyright issues and just don't want to go there. Same reaction to operating my own IMAP server. Too complicated for this casual group of friends to carry on a chat group.


So, although it's not the elegant solution I was hoping for, keeping a Windows system running with my current Outlook rules solution is certainly an easy option.


Thank you for your thoughtful advice. I will act on it.


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Can AppleScript provide my desired functionality (as described) to Mac Mail?

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