Outlook for Mac Autocorrect Bug Fix – Outlook 2011 in OSX Mountain Lion

Outlook for Mac Autocorrect Bug Fix – I use Outlook for Mac 2011 where I work, and I recently upgraded my machine to OSX Mountain Lion.  I hadn’t noticed any problems until today when I tried to type a contraction that started with the letter I…it couldn’t be done.  I would type “I’m” or “I’ll”, but it would automatically capitalize the letter right after the apostrophe and completely lock the email that I was writing.

I'll or I've >> I'Ll or I'Ve

The menu bar would grey out and the computer would beep at me each time I pushed a button.  It was easily the most bizarre problem that I’ve ever encountered on a Mac.  But, after some Googling, I found the problem…

The Problem

Apparently, it is a bug in Outlook for Mac 2011 that didn’t surface until Mountain Lion was released.  The underlying cause?  Autocorrect.  If you’re having this problem too, there’s an easy way to fix it, although you’ll have to do without some autocorrect features until Microsoft releases an update.

The Fix

The fix (though it’s not really a fix…more of a workaround) is to get into your Outlook Preferences, click the AutoCorrect icon, and uncheck the option for “Capitalize first letter of sentences.”  At least, that’s what worked for me.  I’ve read other people who had to uncheck “Correct TWo INitial CApitals.”  So, you may have to see which one solves the problem for you.

Uncheck this box to fix this Outlook bug

Did this work for you?  Did you have to do anything different?  Please let me know and help each other out in the comments.

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About Luke

My name is Luke, and I'm the Online Media Manager for a technology company, photographer, husband, and father. You can see a snapshot of some of my work at LukeCoburn.com. I cheer for the Red Sox and am completely in love with my wife and four little princesses.

39 Responses to “Outlook for Mac Autocorrect Bug Fix – Outlook 2011 in OSX Mountain Lion”

  1. Lisa Welchman September 5, 2012 at 9:20 am #

    Thanks for this. I was contemplating contraction free writing. Weird.

    • LukeCoburn September 5, 2012 at 11:13 am #

       @Lisa Welchman No kidding…I went through the same process.  Thankfully it was a pretty simple solution, and hopefully Microsoft will release an update soon that solves the problem.  We’ll all just have to be attentive to when that happens so that we know that we can change our autocorrect settings back.

  2. xcmom49 October 5, 2012 at 8:05 pm #

    Thanks!  My IT people thought I was crazy when I described the problem.  I had already started to do contraction free writing.

  3. AdamBeaupeurt October 10, 2012 at 1:55 am #

    Thanks for the workaround. I’ve found the simplest workaround is actually as simple as Command+Z. Give it a shot – it unlocks it too.

  4. btmspox October 31, 2012 at 2:11 pm #

    This appears fixed on 14.2.4

    • theanorak November 16, 2012 at 4:55 pm #

      Nope, it’s still not fixed in 14.2.4. I still get the problem when outlook autocorrects two spaced hyphens to emdashes, for example.

      Very annoying.

  5. kmarrs December 2, 2012 at 12:32 pm #

    Thanks. I have also noticed that about 1 time in 5 it will auto-correct “will” to “ail”, and again sends the cursor off the page . Not every time, and I can’t figure out why it does this or if there is a pattern. I tried typing “will” over and over in a long string, and saw that about 1 in every 5 “will”s auto-corrected to “ail” while I was watching myself type the word! WHY ?!?!?!

    Related to the main post above, before i used the fix / workaround suggested (which is working just fine) I noticed when it did the contraction error, it also jumped the font to Consolas, even though that is not a font I use. Everything typed after that was in Consolas, giving it an “HTML off” look, unless I corrected the whole e-mail. Just something to note as another piece of this puzzle.

    • Sandro June 17, 2013 at 4:45 am #

      Have you kmarrs or anyone else found a solution for the problem of “will” and “wil” often (but not always) autocorrected into “ail”?


  6. CGN December 17, 2012 at 9:40 am #

    Turning both “Correct two initial capitals” and “Capitalize first letter of sentences.” off and then on seems to correct the problem, at least temporarily.

  7. Matt February 13, 2013 at 8:42 pm #

    Yes this fixed my issue using Office 2011 14.3.0…
    Currently getting the 14.3.1 update (see if it fixes it)
    Also, CGN method above also does the trick if you would like to leave it on.

    • Luke February 14, 2013 at 11:27 pm #

      Thanks, Matt. Glad this helped.

  8. DMMSquared February 20, 2013 at 12:13 pm #

    I have 14.3.1 and was still having the problem, but after following CGN’s suggestion, it’s currently working correctly. Let’s hope it stays that way… Thanks all… This has been very annoying to me.

    • Luke February 28, 2013 at 8:54 am #

      Awesome. Glad to see that another reader was able to help!

  9. JoshA February 27, 2013 at 9:07 am #

    LOL…Glad you had this post. I am just starting out on a Mac Book Pro for the first time and my immediate thought was. “Damn you Jobs. I’M going to use a contraction and you can’t…can not stop me!”
    Thanks again for sharing.

  10. kmarrs February 28, 2013 at 9:08 am #

    Is anyone having troubles cutting & pasting? Many times, if I cut or copy a sentence out & try to paste it in a desired location somewhere else in the e-mail, it inserts the sentence somewhere else of its own choosing! This is getting very annoying – how can copy / paste NOT work????

    • Luke February 28, 2013 at 6:46 pm #

      I can’t say that I have this exact same problem, but I have had a different problem where when I highlight a chunk of text and then begin to type (overwriting the previous words), sometimes the first letters just overwrite each other. Or pasting a chunk of text onto a highlighted chunk of text will only overwrite some of the highlight part. I hadn’t linked those issues to this autocorrect issue. Do you think they’re related?

  11. Ben Stratton-Woodward March 4, 2013 at 10:21 am #

    In the Compose preferences ensure you UNTICK the option to ‘…reply using the origin format of the message’ for both Plain text and HTML.
    This worked for me and I did not need to unstick and spellchecking which is useful.

    I am guessing that this imposes your formatting preferences at the point at which you edit it.

  12. Sarah MCN March 7, 2013 at 9:44 am #

    This worked! VERY crazy!! I too was thinking of writing contraction free! Thank you for curing my months long headache sans drugs!

    • Luke March 7, 2013 at 1:03 pm #

      Glad to hear that you were able to solve your problem, Sarah!

  13. Susie March 7, 2013 at 8:07 pm #

    On the I’m to I’M situation, you can go to autocorrect and put I’m in the Exception list. that way you don’t lose all your auto correct stuff.

  14. Will March 11, 2013 at 1:19 pm #

    i was able to fix this adding an exception to the rule. From “Autocorrect” window in Outlook Preferences, click the “+” and add “I.”


    Seems to have worked for me. Also still capitalizes “IMDB” and other I-CAPS words.

    • Luke March 15, 2013 at 3:16 pm #

      Thanks for this, Will.

      Everyone else: His link is safe to click. It shows a screenshot of what he’s talking about.

  15. Spencer March 18, 2013 at 11:51 pm #

    If you reply to someone’s email and use a colored font within the body of that email to differentiate responses from questions (or for any other reason), it can get a bit messy. If you add font changes, too, then it becomes hilarious.

    When an apostrophe is auto-corrected to a smart apostrophe, for instance, everything can change format. When I write “change format” I mean: the fonts can change (if there are different fonts in the letter) and the font color can change. By “everything” I mean all the text (original and new) going back to the last line break. The breaks between the changes appear where autocorrections occur. So, the first part may be black until the first lowercase “I” that was autocorrected to a capital “I.” Then the second part may be red until the first autocorrected apostrophe, and then back to black. Each new autocorrect will change the sentence in a fun new way!

    No sense trying to correct the colors and fonts until you’re finished the whole reply. Otherwise, any autocorrect will send the whole thing right back into chaos.

    • Luke March 28, 2013 at 8:45 am #

      Wow, thanks for that, Spencer. I rarely reformat the text and hadn’t noticed this. Do you know whether or not there is any type of fix for this or if it’s a bug that has been filed with Microsoft/Apple?

  16. Pema April 6, 2013 at 4:12 am #

    Wow! Thanks so much for this!! I was beginning to think I was losing my mind. For me, contractions work fine if I compose a new email but only get the autocorrect to I’M or I’Ve etc. when responding. Weird!! Before reading your article, I avoided contractions if it was an important email and with friends and colleagues I stuck a space in after the apostrophe (e.g. I’ m) so it looked less ridiculous. So frustrating. I ended up creating exceptions for these contractions. Thanks!!

  17. glyphic June 1, 2013 at 2:36 am #

    This was helpful. The bug was driving me crazy. Thanks!

    • Luke June 12, 2013 at 12:57 am #

      Glad to hear.

  18. Anand June 24, 2013 at 9:19 am #

    Thank you!!! This was becoming so frustrating! I just unchecked the Correct TWo INitial CApitals, and it seems to have resolved the issue!

  19. ALAN June 25, 2013 at 5:01 pm #


  20. Jason July 1, 2013 at 5:57 pm #

    Thank you!! This was driving me crazy. For me, it was only doing this when responding to someone who sent the email in a text based email; HTML format emails worked fine. I was going crazy trying to work around this. Thank you!

  21. David July 2, 2013 at 7:12 pm #

    Actually I found a slightly different workaround – I just added the letters [I’] to the ‘exception’ box in the correct initial capitals after dialogue box. This allows you to leave the general autocorrect rule in place.

  22. Jon July 29, 2013 at 7:22 pm #

    Looks like the latest Microsoft Update resolves this issue.

  23. Jill August 15, 2013 at 2:01 pm #

    I’ve had to progressively uncheck more and more items in AutoCorrect. Each time I do a Mountain Lion update this problem seems to resurface, either with the contractions, or with dashes. I’ve now got TWo INitials unchecked, as well as first letter and names of days. Hope they get this fixed before we run out of boxes!

  24. Maggie September 25, 2013 at 7:16 am #

    Thank you so much. It had been driving me crazy.
    I note Jill’s comment above, and wonder if microspft is aqare of the problem?
    Thanks again.

  25. Jeremy Smith November 5, 2013 at 12:09 pm #

    What worked for me was simply going to Preferences –> AutoCorrect and unchecking, then re-checking “replace text as you type”. I didn’t have to create any exceptions or leave other boxes unchecked, I simply unchecked and rechecked that box. A gentleman posted a video about this on ScreenCast here (http://screencast.com/t/uPld24YT8FU), but you can try my solution first without clicking on the link if you are concerned about viruses.

  26. BCSouthCampu March 10, 2014 at 9:06 am #

    Thanks, I appreciate it, the first option worked for me.

  27. Jan Oldenburg August 23, 2014 at 12:10 pm #

    I’m so grateful to have found this thread, as I, too, thought I was going crazy. For me it was only “I’m” that was screwed up and adding the exception worked.

    If we’re talking about Outlook for Mac upgrades, thought, how about something that correctly syncs contacts and calendars with Mac contacts and calendar? I’d also really like an option that would allow me to put a meeting or plane flight in with a different starting and ending timezone as Outlook for Enterprise allows….

  28. Brad Scott November 11, 2014 at 1:49 pm #

    I have every single autocorrect settign disabled, and when I type something_like_this in outlook, what do I get? somethingLIKEthis with LIKE in lowercase italics. Fucking insane.

    I hate this thing. I was given it a year ago, it is the bane ofg my existence. I despise everything about the macintosh and mac culture. I want to grind this thing into fine powder and sprinkle it on my food so I can have the pleasure of shitting it out day after day.

    • Scott February 15, 2016 at 12:38 pm #

      Hey Brad Scott – the _like_ is a shorthand way of doing italicized text. I’m a coder and often send variable_names_like_this – when it italicizes the stuff just immediately hit command-z to undo it.

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