For some reason Outlook won't send *.jpg files.  Five (5) 2 mb pix would not transmit ... it stayed in my outbox for 20 hours.  In Windows Explorer I attempted to move the picture file to a new directory ... it would not ... got the message the file was open in another program!  I had to delete the email before I could regain file access.

Attempted to send One (1) 2 mb pic, and the same thing happened.f

Launched my gmail account, attached the same pic, and it went straight through.

Hello,

• Is Outlook appearing any error message related to this issue?
• What type of account do you use in Outlook IMAP or POP?

Solutions:

• Do you have any Anti-Virus program that plugs into Microsoft Outlook? Disable that plugin and try to sending it again.
• Close MS Outlook >> Press Window Key + R (Combination) >> Type outlook<space> /safe & try to send the attachment.
• Enable Clean-boot & then try to send attachments using MS Outlook.

Thanks & Regards

Clark Kent

Hi Tammy,

Which type of email account are you using? IMAP, POP3 or Exchange? Can you send out emails which have smaller size of attachments? Please first contact your mail ISP to confirm if they have a limitation on the maximum size of the attachments.

Does this issue happen with other types of attachments? Such as Word documents or a PDFs?

Please also try cleaning out the Temporary Outlook Files folder and then check if this issue persists. We can find the folder location in the OutlookSecureTempFolder registry key from the following path:

HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook\Security

Please let me know the result.

Regards,

Steve Fan
TechNet Community Support