Office 365 - Outlook error message when sending an email

Error Message: "The operation failed. The message interfaces have returned an unknown error. If the problem persists restart Outlook." By simply recreating a new email with the same message I am able to send. In most cases there are a lot of
attachments that I must search for because I cannot copy & paste attachments from the old email to the new. I have other goofy problems with Outlook but want to deal with this first as it is very time consuming rebuilding these emails.

Hi,
Please create a new Outlook profile for your account to check whether the issue persists. If it works well in the new profile. The issue should be caused by Outlook Data Files corrupting. To create a new Outlook profile, please refer to:
http://support.microsoft.com/kb/829918/en-us
If the issue continues in new profile, please restart Outlook in safe mode(Start > Run > Outlook /safe) to check whether the issue is caused by any third-party add-ins.
Regards,
Winnie Liang
TechNet Community Support

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