How To Auto-Capitalize “I” In Mail, iCal, And All Of OS X
One thing I deeply missed when I started using a mac as my main system was the auto-capitliazation of the letter “i”. When I was typing an email, or document it was almost second nature to just type “i” because I knew that Word would have me covered and auto-capitlize that puppy into “I”. I wouldn’t have to worry that I might look like a fool when I shot off an email or document with lower case i’s in it. Well, hello OS X, the dream OS with funny commercials. Low and behold the all-mighty mac doesn’t auto capitalize i. So when I went to write emails or documents, I had to always remember to go back and capitalize the i’s so I didn’t look a lazy teenager when I sent stuff out. I googled a couple times to find a solution, but nothing stood out as a simple fix. Until I found the ‘Text Substitution’ option which is an OS X option, prebuilt into almost any area where one could type text.
- Right click (or control click) anywhere you don’t actually have text
- Select “Substitutions” -> Show Substitutions.
- Click “Text Preferences”
- Click the + sign on the lower left, and add the substitution i and I.
- Then on the Substitutions window select “Text Replacement”
There you go. And the beauty is that you can do this in almost any area where text is available: Textedit, Mail, Addressbook, iCal, Web Sites, etc.

I have been trying to figure this out since I left Entourage… thank you!
now if someone could provide me a similar fix for initial caps I would be thrilled.
@MikeV: Yes! When I found this I was so happy. Saves me so much time.
@MikeV you mean, where MSWord would autocap a word if it came after a period? That is a great feature, and I’m still looking for a solution. Let me know if you find anything.
yup, that is what I am looking for (in addition to the ‘i’ fix you found)…. If I find something I will be sure to post it up.
Thanks and keep up the good work!
Mike
this is really great. I’ve been trying to figure this out for a while now and just tonight decided to give it another shot.
thanks. I’ll let you guys know if ‘i’ find a cure for the autocaps.
I recently switched from Entourage to Mail and have had the same frustration. This program does auto caps, auto correct, and many other things. I am installing the free trial today! Licenses cost $30-40, depending on which functions you choose.
Spell Catcher
http://www.rainmakerinc.com
Nice. Thanks @Sid. I will try that also. I’m very pleased with the autocap of i. But it would also be nice to auto cap after every period, and other things like i’ve, i’m, etc. (although this can be done with the method above). Thanks for the post.
I must be doing something wrong. THis (Substitutions) doesn’t seem to be available in Mail for me. Oh, and note the double cap in “THis” in the previous sentence. That is an outo-correct I really miss. I’m running 10.5.8
I am also not able to find \Substitutions\ in mail – can any one help please?
Thanks Barry
I am also not able to get to the SUBSTITUTIONS OPTION IN MAIL.
Can anyone help please.?
Thanks
Barry
For autocap: look up WordSerivce from http://www.devon-technologies.com/
It’s free and what it does is to add an option in the service menu to cap all letters after period.
Thanks, @Jonas, I will give WordService a try. BTW the downloads page is:
http://www.devon-technologies.com/download/index.html
To find Substitutions in Mail:
1. start a new email
2. right click in the message body
3. select Substitutions > Show Substitutions
4. select Text Preferences (make sure Text tab is selected)
5. click the + sign in the bottom lefthand corner
6. add whatever you want, such as replacing “i” with “I”
Sadly Substitutions does not work in my scenario – OSX ona Mac book Pro about 6 months old.
It doesn’t even come up!
Is it an option you have to instal please?
Thanks
Barry
I have followed your instructions religiously, and have checked every possible drop down menu in Mail and I definitely do not have a
Substitutions option anywhere. Am I nuts? Or does OSX not have this pre loaded?
Any guidance appreciated thanks
Barry
Hi Berry, I’m not exactly sure why you’re not seeing the options. Here’s a couple things to try:
1) Another way to get the option is to start a new mail message and go to the menu bar, click on “Edit” and down towards the bottom of the list of options you should see “Special Characters”, “Speech”, “Transformations”, “Substituions”. Click the Substituions option and you should then be able to follow these instructions.
2) It could be that your version of OS X or Mail doesn’t have this option. What version of OS X are you running? Feel free to email me [russds . at . gmail.com] if this doesn’t work out. I can also send you a screen shot of the “Transformations” option as it appears to me. (10.6.2) Thanks!
as far as I can tell, this functionality (Substitutions) is only available with Snow Leopard.
I am operating OSX 10.5.8
I definitely do not have Substitution on the edit drop down – it just ends with special characters.
I have found a suggestion that I have to turn this on manually through entering instructions in Terminal some where called Macosxhints but I dont know how to enter teh code into Terminal which comes up with logged on barrysack etc
So I am a little lost!
Any help would be appreciated greatly
Thanks Barry
Barry Sack
Hi Barry, I have found the same as Jack, that this is a feature only in Snow Leopard (10.6). Your best bet would be upgrading. it’s not very expensive, and does give you more hard disk space, I would recommend upgrading. According to Apple this is a feature/enhancement in leopard: http://www.apple.com/macosx/refinements/enhancements-refinements.html