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Hi,
This is Joyce, an Independent Advisor and a Microsoft user like you.
I'm sorry to hear about this issue taht you are having in Outlook. You mentioned that this only happen to specific email? Maybe, the auto complete list on your Outlook is corrupted. You may want to remove that email address from your auto complete list,then type the email address manually instead when sending the message.
To remove an enrty or email address from the AutoComplete cache, follow these steps:
Open a new email message.
Type the first few characters of the AutoComplete entry that you want to remove.
When the entry appears in the list of suggestions, move your mouse pointer over the suggestion until it becomes highlighted, but don't select it.
When the "X" icon appears next to the highlighted suggestion, click X to remove the entry from the list, or press the Delete key on the keyboard.
Selecting X will prevent that entry (name) from appearing in the AutoComplete list again but won't remove it from your account. This entry may still appear in other areas in Outlook (such as search boxes).
Note: If you send a person a new email after you’ve removed their name from the AutoComplete list, their information will be added back to the list.
Hope this helps. Let me know if you have any questions.
Warm regards,
Joyce
*This is a public forum and I do not work for Microsoft nor do I have access to any user accounts.
*My answer will be translated to your language and it might not be precise. I will be posting it in English and hope it helps.