No Auto-Capitalization in Outlook for Mac since updating to 16.108

The issue has been fixed in the latest release - Version 16.108.2 (26042616)

Dear @Brodsky, Alaina @ Corporate Communications, 

Good day, and I appreciate the clear explanation of your concern. As a forum moderator, I genuinely wish I could directly access your account or delve into the backend systems to diagnose and fix this for you. However, our role here is limited to providing general guidance and solutions that can be applied by users.  

I attempted to reproduce the issue in a test environment and encountered the same behavior. In Outlook for Mac version 16.108, the first letter of sentences is no longer automatically capitalized. I also found that multiple Mac users have reported similar behavior, which suggests this may be a broader product issue rather than an isolated configuration problem.

Given the nature of this issue, I recommend contacting Microsoft Support directly for further assistance. You can do this by navigating to Help > Contact Support within the application.

I also recommend asking the Global Administrator in your organization to create a service request with Microsoft Support. A technical support engineer can perform a remote session to investigate the situation, verify the backend configurations, and run any necessary synchronization tools to resolve the problem. If the issue requires further attention, they can escalate it to a specialized team for deeper analysis. For detailed instructions on how to get support, please refer to Get support - Microsoft 365 admin. If you don't know who your IT administrator is, please refer to this article: How do I find my Microsoft 365 admin? - Microsoft Support 

For additional assistance, use this link to find the appropriate contact number from your region: Global Customer Service phone numbers - Microsoft Support 

I know this isn't the answer you were hoping for, and it's disappointing when the solutions aren't straightforward. Please know that as a forum moderator, directing you to the correct, specialized support is the most effective help I can provide from my position.

I truly hope this helps point you in the right direction and that the issue is resolved soon. Should there be any updates on this matter that I’m able to share, I’ll be sure to do so here.

Thank you for your patience and understanding. Wishing you a wonderful day.

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Version 16.108.1 is not auto-capitalizing anymore. This most probably is a bug. However, if you type the word and wait for a second, you will be prompted to auto capitalize. Not an ideal solution but i find it better than manually auto-capitalizing letters at the beginning of every sentence.

New Outlook for Mac Version 16.108

You have hit a known bug. No fix. Just lots of people suggesting solutions that aren't for New Outlook for Mac or that don't work. You can try Microsoft Support, but the reports I've seen don't indicate that they can help either.

https://learn.microsoft.com/en-us/answers/questions/5861502/outlook-not-capitlizing-words

https://learn.microsoft.com/en-us/answers/questions/5863910/capitalise-first-letter-of-sentence

In new Outlook for Mac, sentence auto-capitalization is controlled by the Editor settings, not by the old AutoCorrect dialogs. After the 16.108 update, the setting may have been turned off or reset.

To re-enable auto-capitalization in Outlook for Mac:

1. Start composing a new email (or reply/forward) in Outlook for Mac.
2. On the message ribbon, select Editor.
3. Choose Editor Settings.
4. Turn autocorrect and auto capitalization back On using the toggles.

Autocorrect and auto-capitalize are available for English in Outlook, and these Editor settings are separate from Word’s, so they must be enabled directly in Outlook even if they work in Word.

If the options are already on but capitalization still does not work, toggle them Off, close the message, then open a new message and toggle them On again to refresh the setting.

References:

• Autocorrect, auto capitalize, and auto format your messages
• how to disable "auto-capitalize first letter of sentence" on OUTLOOK.COM email please? - Microsoft Q&A