Dear John Dang,
Thank you for reaching out to the Microsoft Q&A forum. I understand you are having problem with Outlook on the web where typing in Notes randomly switches into overtype/overwrite, and pressing Shift or Insert does not resolve it. I am happy to assist you.
Please note that Outlook on the web does not provide an overtype setting in its options; this is generally controlled by the input mode/keyboard state and can be influenced by the browser environment. Since you already tried the key toggles, please follow these steps:
- Confirm whether the issue is Outlook.com-specific. Open any other website with a text box and type for a minute. If overtype also happens there, the issue is at the browser/OS input level rather than Outlook.com itself. If it only happens in Outlook.com Notes, continue to step 2.
- Test with a different supported browser (same account). Sign in to Outlook.com using a different supported browser and test Notes again.
- Disable browser extensions that can interfere with Outlook.com. Some browsers can have problems working correctly with Outlook.com when ad blockers or pop-up blockers are enabled. Temporarily disable those extensions (or run the browser with extensions disabled) and re-test typing in Notes.
- If it only happens in one browser. If the issue is gone in another supported browser (step 2) or after disabling extensions (step 3), keep using the working profile, then re-enable extensions one at a time to identify the specific add-on triggering the behavior.
- If all steps fail. Use Outlook.com Help (Help on the menu bar, search the issue, then use the “Still need help?” path).
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