Outlook 2010, "The Operation Failed" Sending emails

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Hugo Escobar

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
I have a user who is receiving the error, "The Operation Failed" when sending emails to external contacts. I can fixed the problem by going to File -> Options -> Mail and click on the "Empty Auto-Complete List". I believe it's something with the email address format. When she copy\paste an email address on to a new email and tries to email it, she gets the error. If I empty auto-complete list again and types in the email address she is able to send emails without any error. I can copy\paste the email address to a notepad and then copy\paste the email address to a new email and works perfectly. Has anyone encounter the problem with copy\paste an email address and get the error, "The Operation Failed". Thanks.
 
Yes, only new copy/paste messages. It still happens after Windows profile is deleted.
 
This is exchange, right? I know some imap servers have a problem with the single quotes outlook sometimes puts around an address but it should not affect exchange. what format is the address in? Any odd characters or unusual formatting? (like smtp=alias@domain)
 
Yes, this is Exchange 2010. SMTP. No add simple alias@domain format. What I did end up doing was editing the Cut. copy, and paste. Under File -> Options -> Mail -> Editor Options -> Advanced -> " Cut, Copy, and Paste". I change the pasting between emails when style definitions conflict to: Keep Text Only. Not sure if that was fix, but waiting on the user.
 
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