Mac Mail vs. Microsoft Outlook: The dirty truth

Erik Eckel takes a look at how Mac Mail performs next to Outlook for Mac. Which do you prefer and why?


Sometimes, I find myself wanting to become an Apple fanboy. It would be easier, after all, within the hectic, ever-changing IT industry to just know I can trust what the manufacturer tells me. But years of technology consulting have taught me that vendors are evil.

Yes, it’s true. I’m sorry you had to read it here. But that's the way it is in the real world, where the consulting firm I operate services hundreds of different commercial businesses and organizations. Vendors will promise you the world and assure you its mail client (or other product) is the best. However, your experience may differ.

Even before I began offering IT services to others, family and friends purchasing new Macs would frequently ask which email client is the best on OS X. I’ve always been partial to OS X Mail, which should make Apple developers happy. They’ve earned the accolade. The app is integrated within the OS, loads quickly, boasts a basic but attractive interface, possesses clean and well-laid elements, and proves to be easily navigable. Composing messages, replying to email, and sorting the inbox are painless tasks. Creating rules or email signatures within Mail doesn’t induce knee-knocking anxiety, the way doing so might in, say, Microsoft Outlook. Mail is simple and not that complicated, and the resulting lack of complexity makes it more approachable.

Microsoft’s older Entourage applications, of course, earned little popularity. Rightfully so. Many Entourage users complained of database corruption and slow performance. Microsoft wisely replaced Entourage with Outlook. With Outlook for Mac 2011’s release, I was hopeful that a new standard was in hand. But I’ve been disappointed. Outlook takes longer to open (my scientifically invalid, non-double-blind testing shows Outlook requires 23 seconds to open, whereas Mail requires only five), regularly encounters synchronization delays, and often simply doesn’t update my Exchange mailbox with changes as accurately or rapidly as does Mail, at least in my experience.

Ultimately, I use both Mail and Outlook for Mac, if for no other reason than to stay current with both platforms. I’ve configured the Macs in my home and business to connect to POP3, IMAP, and Exchange accounts, too, and I access mail, contacts, and calendars using Outlook and OS X’s built-in Mail, Contacts, and Calendar. Apple’s unending efforts to improve Mail, including message integration within Notification Center, iCloud reliability improvements, and Conversation views are encouraging and continue to make Mail a favorite application.

However, Mail isn’t perfect.

Outlook, ultimately, gains an edge due to the clean manner in which it successfully integrates contacts and calendaring. Opening shared calendars, in particular, is easier within Outlook, in my opinion, than within Calendar. And Outlook consistently displays HTML email messages, specifically marketing messages that I’ve requested to receive, properly.

Mail stumbles on that front. Marketing messages that are sent by large, well-known firms you would recognize (ThinkGeek, Barnes & Noble, and NPR are a few examples) and may also receive within your inbox, regularly fail to format properly within Mail. That’s frustrating.

So, it’s a tradeoff. If you want the ease of use and generally acceptable performance Mail provides, you can save hundreds of dollars per Mac leveraging Mail instead of Outlook. But if you operate within an enterprise environment, you may well not have time for workarounds and simply find Outlook the best fit. But if you or your users also need Word, Excel, and/or PowerPoint, Outlook’s almost certainly going to be included with the license your organization purchases, and firing up Outlook becomes a no-brainer. Just be sure to give Outlook time to open and then sync changes with Exchange before exiting the program.

Which do you prefer: Mac Mail or Outlook for Mac? Share your opinion in the discussion thread below.


You forgot to mention that OSX (Mavericks) Mail randomly deletes email.

Yes... stuff that I want to save is gone on a daily basis... what a piece of junk!


Here are some pluses and minuses

 I some secondary e-mail addresses that are connected to my domain name.

CPanel seems to generate A connection to outlook very easily.

I may contact my website hosting company to see how connection to Apple Mail would work.

That said I may use both......... Apple Mail for my critical Business e-mail

Outlook for noncritical business and personal E-mail addresses

One last note about Microsoft my Mac never crash until I installed Microsoft office

there is an annoying Microsoft Word Control center background that doesn't seem to want to go away.

For that reason I may just cancel the trial or subscription and stick with Apple mail

Apple Mail really has become more elegant and how it handles conversations you can highlight and bring forward parts of a conversation and respond to them individually

I am wondering if and when Contacts Will link directly to A list of e-mails from a particular contact

perhaps that fancy feature will come later

I preferred Mail for several years. Mavericks has changed that. It's finally Gmail-friendly with 10.9.2, but Mail on my iMac still taxes cpu like a madman, fails to display approximately 50% of new messages in the inbox unless I leave/return to the inbox, and resurrects many previously-deleted emails.

Outlook -- Is there a way to turn off those insidious tooltips? They actually cover up what I'm attempting to read. Search Google to see how annoying this is in Mac and Windows versions. Microsoft has had YEARS to fix this obvious oversight -- at least give us the option of turning tooltips off. That's problem #1 of a long list. Outlook does a few things extremely well. You can move an email to any folder in any account just as quickly as you can in Mail with the awesome Mail Act-On utility. Finding and opening that folder -- different story. It's difficult to believe that anyone in Redmond actually uses Outlook 2011.

My most reliable email application is Mail iOS. I have tried numerous Mac applications since getting Mavericks. Like Outlook, most do a few things well, but have enough problems to make the app unreliable, annoying, or both. Anyone who creates a reliable, easy-to-use email application for Mac will be quite rich very quickly.


I was a bit of a power user in Outlook for PC before switching to a Mac. The 1st drawback of OL for Mac was the font incompatibility - perfect-looking messages show up in the recipient's mailbox looking like they were written by a 3rd grader. But that's a platform issue rather than an Outlook issue. 2nd drawback was that the functionality in terms of formatting emails isn't as broad in the Mac version and I missed that ability. 

The kicker, and why I'm using Mail even though I preferred Outlook was that Outlook crashed. Badly. I lost about 14K messages, which had all been organized in folders. I had to reinstall Outlook and re-download everything. In fact, I had to reinstall my entire OS. Then it happened a few more times. So, once it was corrupt on my MacBook I spent countless hours trying to fix it with tech support and then gave up. I have since migrated to using IMAP, which of course would have helped but it was a very bad experience. I also learned that you need to back up your Outlook outside of time capsule, which won't properly restore outlook for Mac. 

Hope this saves others the heartache I experienced. 


Recently switched to a Mac from a Windows 7/Outlook 2010 environment. Company uses enterprise Gmail, so Outlook was using the Google App Sync. I was relatively happy with Outlook in that environment, but when switching to a Mac I really wanted to avoid running a Windows VM if at all possible, and stick to a pure Mac environment. 

Setting up Mac Mail 7.2 with multiple Gmail accounts was relatively easy, although I wish I could have specified how much data I wanted to download locally. I am a pack rat so it took a while to download all of my email, and I'm sure a significant amount of space.

I had to make some adjustments to the SMTP servers after the fact, like changing the port numbers and my user name. The wizard didn't set that up properly for me. However, once it started working I have been extremely happy with the Mail application. Especially helpful is the Junk mail feature. Getting that to work in Outlook in a Gmail environment is nearly impossible. In comparison, I am easily able to filter Junk email with the Mail 7.2 application.

About the only thing I am missing is a 3rd party WebEx plug-in for the Calendar application to automatically create WebEx meetings as part of my calendar invites.

So far I am loving Mail 7.2 and my Mac, especially the Spotlight search which searches EVERYTHING, including Mail. When Microsoft stopped including emails in their global search (Windows 8/Office 2013) I stopped upgrading my OS and Office from Windows 7 and Office 2010. Now that I'm on a Mac again after about 20 years of being away I'm loving it.


Outlook does not support iCloud Calendars and Contacts - a big negative for Outlook (since I use iCloud). On the other hand, Mail does has some glitches with Exchange calendar invites, exchange mail syncing, and rules.

Outlook Pros:

• Seamless Exchange support

• Advanced calendar invites and scheduling

• Customizable categories

• Integrated task list with email message flags (To-do, completed, etc.)

• Better email attachment 

Mail Pros:

• Cleaner design

• Calendar interaction & multiple source support

• Seamless iEverything integration

• Exchange support

• Auto event creation directly from mail messages and Safari (just click date text)

• OSX Notifications integration

I've flip-flopped between them many times, but I am ultimately stuck with Outlook because my office is on Exchange and the items in the pro list supersede the Mail pros. I wish I could get all the Outlook features I like in Mail!


However, apple mail is giant player for the functioning of speedy & reliable mail service but Outlook 2011 is well know for its enriched features. Most of guys are loved Outlook 2011 for ease functioning. In case, anyone is interested to migrate from apple mail to Outlook 2011 then easily can be done through Microsoft certified stellar apple mail to Outlook 2011 converter available.


I've been a jumping jack for quite a while and I have had the oppty to use all the three....MS Outlook, Thunderbird ,OWA and OSX Mail . 

I definitely would vote for MS Outlook.

Let me share the main issues using OWA, Thunderbird, Mail etc :

1. The fonts and formatting is a pain in the ...! I format it so carefully as it is all for business and I see that my font varies from time to time .It never had the consistency . Mail default font is Helvitica and most of the users may not have that and it shows in Times New Roman, which definitely is old fashioned and looks weird with the signature being in some xyz font.

2.Mail receiving and forwarding in Mail and thunderbird is little time consuming and you wouldn't know if the attachment is there or not. In outlook and owa you can see that there are attachments attached under the subject box.

3.Sending calendar invites is little difficult in owa, mail and thunderbird. In Gmail and MS outlook you have the insert option/invite option on top which is very easy.

will be thankful if any of the mail users can share their best experiences in using mail and tips to make my MacBook mail experience better.

Thanks in advance .

Cheers :)



My answer is- NEITHER.  I moved to the Mac platform for much the same reason as you- to move to a single-vendor, controlled platform, and for the most part it's been...OK.  I guess I was hoping for the heavens to open up and bestow the wisdom of the late Mr. Jobs upon me.  Still waiting for that.

However- the mail experience has been horrific on both fronts. My firm uses Exchange, recently moved to Office365 (the same thing but 'out there'), for a remote worker there's no effective difference.  Do you want to know what I need to do to be "mail functional"?  I have to have Parallels and use MS Outlook 2013 in a windows VM, or, if I'm online, I find it even easier to RDP to a VDI workstation in my office and run Outlook there.  Outlook 2011 is awful and a resource hog.  It's also not fully baked in with Exchange 2010/2013.  OSX Mail is a clean app, but definitely made for the gmails/imap/pop accounts of the world, NOT enterprise messaging apps.  

I've even found OWA in safari or chrome to work better than the two.  I'd advise Microsoft to take their OWA app for iOS and port it to OSX and I think I'd live in that!  (Hey, M$, you listening??  Do THAT.)

My two pence.  Which is worthless since I'm American. ;)


Thanks for sharing, Erik. I wouldn't say that adding contact details is as seamless as you say, though adding calendar events is nice.

I switched back to Mail after Outlook for Mac 2011 significantly slowed my Macbook Pro (late 2008.

I would like to keep MS Excel open without all the rest of the background processes and sync processes running, but haven't figured that one out.

Oh yea, and Outlook 2013 for PC was horrible. 

Claire Higgins
Claire Higgins

Having used Entourage for many years, I recently purchased a new laptop and rather than purchase Outlook was pursuaded to give Mail a go.  I'm not getting on at all well with it.  One of the main problems I have is when sending image attachments it seems to randomly embed the image into the email despite checking the box for windows friendly attachments. Has anyone found a way around this problem?


Quote: "So, it’s a tradeoff. If you want the ease of use and generally acceptable performance Mail provides, you can save hundreds of dollars per Mac leveraging Mail instead of Outlook. But if you operate within an enterprise environment, you may well not have time for workarounds and simply find Outlook the best fit."

This sums up my experience as well. Although it is possible to cobble together a workplace solution from Apple-developed applications, they are nothing like the connectivity that Microsoft products provide out-of-the-box for business use.

For those whose core applications require running another OS (Mac OS or Linux, for examples), I have found running Office in a "winebottle" created by CrossOver, for example, to be an effective and easy to maintain solution.


I make extensive use of Outlook Tasks functionality (in Windows). I have not found anything in the Apple (or Android) ecosystem that comes close in functionality and lets me share task info with my windows machine. For that reason, it's Outlook in Windows for me.


Outlook undoubtedly has the best Exchange support so it gets my vote.


I find myself in Thunderbird more than any other mail client. My big issue is that I develop cross platform apps and find myself mostly on some flavor of linux, alot on Macs and occasionally on Windows.  Tbird behaves the same.  I use imap on my servers and the University uses Exchange.  

I don't really disagree with anything the author said and Mail and Outlook do work but only on some of the systems I work with.


I am speaking from an experiential point of view in having had to provide Tech Support for many email issues with MACS, IPads, & IPhones for the last few years so I am well acquainted with the downside of email clients on Apple devices as well as windows based devices. I freely admit I have always been more of a Windows guy than an OSX guy and have a built in prejudice favoring Outlook. Having said that I would like to make a few observations that may be of interest. One is my surprise at the large percentage of die hard MAC users that actually preferred Outlook to OSX Mail that I encountered while providing tech support. The main problem with Apple Mail or Mac Mail is as with any client there are times one is forced to remove an account and reinstall it to correct problems and when you do this you lose everything. Any saved emails are history. While that can happen with Outlook usually if you remove an account & reinstall it your saved emails are still there. The other big negative I encountered was when Apple came out wit the iOS6 upgrade it pretty much bricked everyone's email accounts on their I-Phones and I Pads and the only solution we ever found was to remove  the account and re-enter it on the device. Most small businesses have saved emails they do not want to lose but if they weren't archived on the server they were just SOL.

Larry Levine
Larry Levine

Everytime I try to stop using Apple Mail I keep finding my way back to it.  Thunderbird, Postbox, Outlook, they all have their pros and cons.  But I'm a mail purist.  And gives me the least hardship with a task I have to do all day and night.  I don't want a lot of integration with other things when it comes to a mail client BTW - so I may not be your best person to ask :)


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