Time to Move from Mail to Outlook on the Mac?

Hi All,

I’m getting frustrated with Mail on the Mac. Specifically, the search in Mail is terrible (I have to go to the gmail web interface for reliable search) and I hate that I have to rely on a 3rd party app to get Mail to do what I want (SmallCubed).

Is it time to move to Outlook?

I’d love to hear from those that have made the jump as to pros and cons or people that use both.


Careful what you wish for.

My wife uses both as old macOS version of Mail (on non-upgradable MacBook) doesn’t work with new Microsoft Exchange at her university. She notices no differences, but is not looking for them.

Perhaps if you have search problem with mail, rebuild the mailboxes? I’ve never noticed searching fails with Mail. Perhaps as you appear to be searching a Google mailbox this has something to do with the issue? I have a vague recollection they use their own version of IMAP (others can comment on that).

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Outlook for Mac just became a free application: Outlook Mac for All - Microsoft Community Hub

Edit: reading the comments i see: “The new Outlook for Mac is free to use, and ad-supported when using a non-licensed account.” … :frowning: … could be a reason to avoid it when you do not have an Office license/ M365 subscription.

Personally, i do not like the integrated mail, calendar, to-do concept of Outlook. I need to use Outlook for work, and it is feature rich, but i prefer the web interface.

Since Ventura Apple Mail search improved the experience a lot for me.


It really depends. If you’re using an Exchange email account then I think it’s worth switching. I’ve used both mail.app and Outlook and they both have plusses, but you can do more with Outlook than you can with Mail. And mail doesn’t seem to refresh the inbox as quickly as the new Outlook does.

If you’re using Gmail, I’d say neither. Take a look at Mimestream. It’s pretty awesome, it gives you pretty much the full gmail functionality but in a local Mac app. I now use Mail.app for iCloud and Fastmail (my personal accounts), Outlook for the office account, and Mimestream for all my gmail accounts (I’m a board member at a bunch of institutions and they all want us to have email accounts that they host for security reasons.)

It’s kind of annoying not to have a single client, but it does help me keep straight what role I’m in as I’m interacting with folks by the various email services.


I prefer Apple’s Mail app because Outlook feels very cluttered to me, but search is so bad (tried rebuilding mailboxes and every other “fix” under the sun that I could find) that I will often use Outlook just to search.

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I agree, it has many options and they can easily overwhelm. The new Outlook does have a cleaner interface and looks rather nice I think. But still Apple Mail has a cleaner interface and is more integrated in the OS.

I noticed that Outlook for Mac now also syncs calendar items for iCloud accounts, it did not do that before out-of-the box which is a nice addition.

Mail uses Spotlight to find messages so the problem is probably local, especially if the needed emails are older than a day or two.

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Thanks. I had that recollection also. Then maybe next step might be to rebuild Spotlight index. Can’t hurt.

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I’ve switched to Outlook… my company account is Microsoft 365, but I also load my personal Gmail account into it and my iCloud calendar. All work very well.

It’s helpful to have the additional Office 365 mail functionality, like presence indicators, quick reactions, server-side rules and priority. Search is excellent. Having my agenda on the right hand side of my mail is very useful. The focused/other inboxes works well and I fine tune that as I go.

They need to improve integration with Microsoft To Do, but it works well enough.

Overall, if you use Microsoft 365 I’d recommend giving it a spin.

Not directly related, but I recently discovered Microsoft Power Automate, which I’m using to automatically save email attachments received by my 365 account to OneDrive, which are in turn imported by EagleFiler. There’s lots of clever automations available there.


Power Automate is great! I’ve created a number of flows to move data around. For example, I have a flow for notification emails that creates a task in Microsoft To-Do with the corresponding information and deletes the email. I also have a flow that updates a Microsoft List that I trigger with a Siri Shortcut.

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).


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).