Time to Move from Mail to Outlook on the Mac?

You mentioned earlier you use Mimestream. If you are a Gmail user why not use the web client? Both it and the Gmail iOS app offer scheduled send.

I run my Google Workspace account in Google Chrome and use Edge or Safari for everything else. I normally keep two browsers, thunderbird mail (for backup purposes only) and multiple other apps open on my 8GB MBA without any problem.

I just switched from Outlook on Mac, iPhone, and iPad to Apple Mail, and prefer Mail. On my Mac, I’m using six IMAP accounts, and on iOS I also have a Gmail and Yahoo account (I use Safari for the web interfaces of those on my Mac).

It was easier to review messages in the messages pane in Outlook, and attachments were not inline and awkward. Outlook on iOS pushed messages to my phone continually while somehow using less battery.

But otherwise I like Mail better. For me, search is much better with Mail. (Although, in fairness, I sometimes can’t find messages because they’re buried in threads and I’m still trying to learn how to navigate how Mail does threading.) Also, it’s easier to move messages to folders based on projects.

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Mail could do so, too!

Why do you not integrate them with Mail on the Mac?

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My experience is search in Mail.app is miles ahead of search in Outlook. But that could be my personal setup.

I ditched Outlook as soon as our company moved to a cloud based setup, mainly because Mail app is much quicker and less prone to bloat. And I include traffic bloat in that… Man does Outlook phone home a lot (= to MS, not to my email servers)

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You’re right. The gmail web interface is good in terms of functions but there’s something about a nice clean UI. Their UI just doesn’t do it for me.

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I use Spark. Apple Mail, and Outlook for the Mac which, at least on the desk top, is restricted to my work accounts for focus. I do have all my email accounts on the mobile outlook version.

My biggest issue is the inability to move a message between accounts. I have an old gmail address that is my catch all when I have to sign up for access and have concerns about privacy/marketing. I don’t need to see every special offer in my work flow. However, there will be something that comes in that I want to route to work but can’t drag it over to the appropriate folder.

New Outlook also suggests where to search when I want to attach something instead of take it me to Finder. I wish that I had the option to move back to the older Outlook (the software update no longer made it optional). The new format, imo, is not as professional in appearance. I don’t need to see everyone’s icon.

I will continue to use Outlook for the Mac but I am not giving up mail or spark.

I understand. I’m the opposite, I normally choose function over form. Maybe because I started with a command line interface. :older_man:t2:

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I don’t understand why in Mail attachments get inserted all over the place. Like literally between words. Makes no sense.

Another advantage to me of Outlook is the keyboard shortcut to move emails into folders. As far as I know, there is nothing similar in Mail unless you are maybe using something like Keyboard Maestro.

What I like the most about Mail is the integration with Siri. If I have an email open on my phone, I can just ask Siri to “remind me about this” and the email gets added to Reminders.

I may have more time to explain, but I find Outlook for Mac (which I must use for work) very frustrating. I wouldn’t install it for my personal use even if you gave me a new maxed-out Mac Studio with a Pro Display XDR to replace my mid-2014 MacBook Pro…


I use Outlook for work, but mostly use the web interface because searching in Outlook does not work properly for me. The web interface is a lot better in that regard (and to be honest in every other regard also). With the recent updates on Mail.app search works fine for me also and it is also my experience that it is better than Outlook. It might be related to types of account used in Outlook.


On Hookmark’s website, we published some info about Outlook , AppleScript and linking: Using Hookmark With Microsoft Outlook – Hookmark. It’s their

  • Feature ID: 88537
  • Added to roadmap: 12/8/2021

Personally, I’m happy enough with Mail.app. As we learned on a MPU podcast, Apple have expressed their commitment to AppleScript.

Personally I would put AppleScript in the same category as Apple Remote Desktop. Software that still exists long after Apple has lost all interest in it. ARD sells for $80 and has been receiving mainly 1 star reviews for the past 10 years.

Apple eliminated the position of AppleScript product manager in 2016.

they don’t look keen on extending it. But at least they’ve been fixing issues with it.

A quick plug for Mailmate, which I see I’ve been using for almost exactly 10 years… and its search capabilities are a big part of the reason I stick with it. (Another is that I like writing messages in Markdown).

For example, in addition to just typing words into the search box, you can use an abbreviated search syntax based on single letters.

If I want to find my messages from Christine, I enter f christine. If I want messages with ‘cambridge’ in the subject, I say s cambridge. And if I want messages to Phil with ‘mac’ in the subject, I can type t phil s mac.

Once you get used to this, it’s really fast, and it searches my third-of-a-million messages in an instant.

There are lots of more sophisticated examples like:
foo f !smith t (smith or joe) d 2y
which will find messages containing ‘foo’ that aren’t from ‘smith’, and are addressed to ‘smith’ or ‘joe’, received in the last two years. But no, I don’t normally go that far!



Thanks, Ulli! I tried integrating them both. Gmail has worked out well. I no longer use the web interface for most things now.

Yahoo did not go so well regarding the handling of spam (I couldn’t whitelist a sender and put their message back into the Inbox once it was put in the Spam folder). I still use that on my Mac through the web, but on my iPhone and iPad with Mail.

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I use Yahoo very seldom today, but I could not remember to ever had a problem with that.
I have within the Mail Settings of the Yahoo Account the setting for Spam set to the Spamfolder on my Mac.
Also if I want to Whitelist someone, I normally put that address into my Adressbook.
Additional I use SpamSieve since a longer period of time, and with some very annoying Exceptions, it works very well in handling my Spam with all my different Accounts.

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I actually did move to Outlook. This is much to my surprise since I have always tried to avoid MS software.

I gave up on Mac Mail many years ago when it had problems with gmail, and even though those problems have been resolved, I never went back to it. Also I moved away from gmail to fastmail so it is sorta moot anyway. I have used several email clients along the way including Postbox (which I liked but moved on from several years ago because it was eating too much battery) and Mailmate (which I also liked). I started pondering an alternative Mailmate last year – I fancy myself as a power user in general, but I decided that I didn’t really need all the power of Mailmate although it did do some neat things.

I decided to tinker with Outlook and was surprised to find that it was an acceptable solution. My main email account is IMAP (fastmail) which it handles just fine, and I have two exchange accounts for outside organizations that I work with. I find the Applescript support to be excellent which is important to me.

There are a few things that I don’t like about outlook – it doesnt integrate well with Apple contacts, for example. I have to import them into Outlook. But overall the experience has been pretty good.

(I did try thunderbird for a while, first, and it was fine except for the lack of Applescript support. I probably would have stayed with that otherwise).

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I use SpamSieve and love it. :slightly_smiling_face: Right now my only Mac is a MBP that I bring back and forth to the office. One of my main goals in getting a Mac desktop (probably waiting for the M3) is to have a machine running SpamSieve all the time so I won’t see spam on my iPhone and iPad when my MBP is not online.

Can’t stand the ms silo on mac.

Mailmate in my opinion is the best mac imap power user mail app on the planet :grin:

I have tried a zillion mail clients. Always falling back to Apple Mail, because it works.
Searching also works 100%. (However, I don’t like that they changed the behavior in Ventura – After doing a search, you must empty the search field to go back to “non search”).