The other thing that I have noticed is that it doesn’t work with Outlook.com. So if you have plugins (like Mailbutler) that work fine on Apple Mail, it is not supported on Outlook because (as of now) you can’t use “Microsoft Cloud” with Outlook.com (only GMail).
I use the Mail.app for browsing, reading and sending mail. But switch to the Gmail app for searching. I don’t search as often as I write and read emails, so this is a good compromise for me.
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Thanks, I do use Mimestream strictly for listserv emails. My original intent was to test it with these emails and if it was good, I’d replace Mail. I’m not super impressed with Mimestream. Just doesn’t do it for me.
I went ahead and made the jump and I was testing Outlook this morning (I have Microsoft 365). The interface seems cleaner and more modern than Mail.
My big gripe right now is I can’t find a way to schedule emails to send at a later time (for instance, tomorrow at 3:08pm) and I can’t find a way to delay send for lengths greater than 20 seconds (via Undo Send). I think if there’s a reliable way to delay the sending of all messages by a few minutes and a way to schedule emails to send some time in the future, I’d be all in.
I’m a daily “power” (4 accounts) Outlook user and love it. But if I were a gmail user I’m pretty sure I’d be using something else.
That said, Outlook on macOS has the send later option for me. After you’ve composed a message, instead of clicking the send button, click the arrow next to send and “Send Later” appears. You can then schedule it for whenever you want. The message is stored (for Exchange accounts, at least) server-side, so it will send even if your computer is turned off. Come to think of it, that makes me wonder if it’s an Exchange only feature that doesn’t work with gmail accounts?
I recently moved to Outlook because of many missing features in Mail and sync issues with Exchange and Apple Calendar (my devices were never in sync!).
So far, I’ve been really happy. I can finally trust all my devices as the calendar is always in sync, the interface is faster than Mail, especially when updating the Inbox, and I can book rooms and view the availability of my colleagues when scheduling meetings. All these things were not possible with stock apps.
I’ve also been pleasantly surprised with the rich ecosystem of add-ons - these have great integrations with Zoom, Dropbox, and many other services.
I also find the search is much more reliable than Mail.
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How do you deal with links to specific messages?
So far, it’s the only thing that’s keeping me in Mail.
I’ve never needed links to emails, so I don’t know if it is supported.
If you use MS apps, emails are automatically linked to tasks and events. Tasks in ToDo are automatically linked to flagged emails, and emails appear in the Calendar when you create an event from an email (the entire email thread appears in the event).
I just checked and send later is only available on my Exchange account, not Gmail (presumably because it’s done server-side on MS servers).
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This isn’t possible, except within the MS ecosystem as @Rob_Polding describes.
Hookmark has a rather basic workaround, as currently the ‘new’ Outlook doesn’t support AppleScript. The good news is that AppleScript support within Outlook is due very soon (possibly this month, if the roadmap is accurate), so that should open up options for linking (and for single-key email archiving to EagleFiler and similar application).
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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. 
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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…
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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.
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