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Outlook errors: "This is not a valid file name" and "Cannot send this item"
Date Added: 11/9/2021

Outlook errors:
1) "This is not a valid file name"
2) "Cannot send this item"
These errors can occur while typing a reply to an email and Outlook either tries to save the email as a Draft or you click the Send button. When the error happens, you will lose all the content you've typed with no way of getting it back, so if you're experiencing this problem, you'll want to write your text in notepad and then copy/paste that into Outlook until you get it fixed.

Cause:
Outlook bug as of 11/9/2021. Outlook has some problem with the content of the email you're working on. Probably a very long URL in a link.

Solution:
Convert the email to Rich Text, and/or remove links from the email, especially any very long links. In my case, I just erased the older emails from the reply chain below my response. Once you have removed the offending content, the email will send with no problems.

Reference:
https://support.microsoft.com/en-us/office/outlook-error-cannot-send-this-item-when-replying-to-an-email-9346c0cd-06c8-4491-b5bf-0b91909c377d



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