Hi Christina,
Welcome to Microsoft Q&A.
In Outlook.com, typing in the To/Cc/Bcc box doesn’t always search your Contacts “live.” It relies heavily on a Suggested recipients / auto-complete cache built from people you’ve emailed and saved suggestions. If that cache gets cleared, corrupted, or blocked by browser site data/extensions, you can type A–Z and still see nothing, even though your contacts are safe in the People tab.
For reference: Manage suggested recipients in the To, Cc, and Bcc fields in Outlook
Fix 1: Force-reset Suggested Recipients
Because the standard steps didn’t help, try a full reset + toggle. Menu wording varies by rollout, so use whichever path you see:
Path A (common in current Outlook.com rollouts):
- Outlook.com > Settings (gear) >General > Privacy and data
- Under Suggested people, select Clear data
- Toggle “Suggested people” OFF, wait ~10 seconds, then toggle it ON again
- Sign out of Outlook.com, close the browser tab, reopen, sign back in, and test.
Path B (some layouts show it here instead):
- Outlook.com > Settings (gear) > Mail > Compose and reply
- Look for Suggested recipients / autocomplete and clear/reset options (if shown), then sign out/in and test.
Note: The OFF/ON toggle isn’t an “officially guaranteed” step, but it’s a practical way to force Outlook.com to rebuild the suggestions connection when clearing alone doesn’t stick.
Fix 2: Quick workaround to send mail right now
If suggestions still don’t appear while typing:
- In the compose window, click the word “To” (it’s clickable)
- Use Add recipients / People picker to search and select your contact(s)
This picker is the reliable fallback when a name doesn’t show in suggestions.
Fix 3: Rule out browser/site-data issues (fast test)
Try Outlook.com in an InPrivate/Incognito window
Or test a different browser (Edge/Chrome/Firefox)
Temporarily disable ad-block/privacy extensions for Outlook.com. If it works in Incognito then it should be site data or an extension.
Please let me know if this proves useful to you, or if you would like assistance in navigating Microsoft's support channel.
I'm looking forward to your answer.
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