Using Classic Outlook on Windows for personal email, calendar, and contact management
The behavior is caused by a bad/invalid entry in the Outlook AutoComplete (nickname) cache. Because the cache is corrupted or the UI no longer shows the delete “X” for that entry, Outlook keeps forcing the wrong address even after clearing the list once.
Use these steps that are supported in the provided documentation:
- Verify AutoComplete is enabled
- In Outlook, select File > Options.
- Select the Mail tab.
- Scroll to Send messages and make sure Use Auto-Complete List to suggest names when typing in the To, Cc, and Bcc lines is checked.
- Clear the AutoComplete list from Outlook (classic)
- In the same Mail options page, under Send messages, select Empty AutoComplete List.
- Confirm by selecting Yes.
- Close the dialog and restart Outlook.
- Send a few test messages to the correct address so Outlook can repopulate the cache with the correct entry.
- Remove the bad entry directly from the suggestion list (where supported)
- Start a new message.
- Type the first few characters of the problematic address in To.
- When the wrong suggestion appears, hover over it until it is highlighted.
- If an X appears next to it, select X, or press Delete on the keyboard while it is highlighted to remove it.
- Next time, type the full correct address; it will be added back to the AutoComplete list.
If the AutoComplete feature is enabled and the incorrect suggestion still appears after clearing the list, the AutoComplete cache is considered corrupted and must be deleted/reset as described above. Outlook will then rebuild the cache from new messages that are sent.
Note: Some recent Outlook builds have reduced or removed the ability to manage individual AutoComplete entries (for example, the missing X icon). In those builds, only clearing the entire AutoComplete list is available, and individual bad entries cannot be permanently removed beyond that.
References:
- AutoComplete not working correctly in Outlook 2010
- Outlook does not add recipients to the Auto-Complete cache
- Outlook replies or forwards cause non-delivery error “Your message did not reach some or all of the intended recipients”
- Fix NDR error code "550 5.1.1" through "550 5.1.20" in Exchange Online
- Outlook 365 Classic Autocomplete gone strange - Microsoft Q&A
- Unable to remove autosuggest email from Outlook - Microsoft Q&A