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Outlook for Mac: So Close!

Outlook-iconI spend most of my working day reading, writing, sending, and managing email — so the tool I use must be as efficient as possible. When I was on Windows, I was an Outlook power-user. I really came to hate Windows back then so switched over to Mac. I loved everything about my new Mac experience… except I missed Outlook.

So I embarked on a year-long project to find an Outlook replacement. I tried many different calendar and email options on the Mac, and I finally had to conclude that Outlook for Mac is the best thing out there.


The way that email and the calendar are two sides of a single app is THE way to work, and as far as I’m concerned, nobody does this as well as Outlook. It is very convenient to have your contacts/address book integrated with your email and calendar as well, but so far I still use the native Mac Contacts app. This is a bit inconvenient, but since my computer use blends across multiple devices, I must stick with what will translate across devices… which is where things get just a bit complicated.

iDevices do Outlook too

I use Outlook on my iOS devices — an iPhone and iPad. It’s great, but I think it’s only great because I have all my email accounts set up as IMAP.

However, because I do not have an Exchange account, running Outlook on multiple devices only coordinates my Email. Calendar items and contacts do not sync between devices (at least not that I’ve been able to figure out, and not for a lack of trying). I decided that I can live with having my calendar only on my laptop, but I can’t have that for my contacts: so my Contacts are not in Outlook.

Outlook nits that still need work

So even though I recommend Outlook for use on a Mac, there are still issues that I wish Microsoft would address:

  • The Mac version doesn’t have the same power with rules that the Windows version does — but it’s still just as good as other Mac email apps out there when you take ease-of-use into consideration.
  • Dragging files into folders doesn’t always work. This is inconsistent. Usually it works fine. But sometimes, after a few tries I give up and use the right-click menu to choose a folder which is far less efficient. (This frustrates the heck out of me!)
  • The Outbox is only visible/accessible when there is something in it. (Yes, there ARE reasons to want to be able to access it all the time!)
  • The Sent, Drafts, and Outbox folders are positioned at the BOTTOM of your folders list (I wish this was configurable).
  • When I delete reoccurring meetings from the calendar, they mysteriously reappear a day later (although I hear Windows users are suffering from this one as well). This has been a HUGE problem.
  • Often I cannot rename a folder: I must repeatedly try it 5-6 times before it finally lets me edit it.
  • Anytime I exit the application, when I go back into it, I must reactivate. (This obviously is an Outlook365 issue, however note that my other Office365 apps don’t do this to me — only Outlook.)

And for Pete’s sake Microsoft and Apple! When are you two going to play together so that Outlook content will synch to my iDevices!?