I have a user who sent an attachment to 500 users (different emails) in BCC.
About 20 of them are missing the attachment. This user sent this message
with attachment to different recipients located in gmail, hotmail.com,
msn.com, caramail.com.....
But this user can send this email with the attachment file to those
recipients one by one and the email reaches the recipient with the attachment
file.
Sometimes, he experiences the issue when he sent an attachment to 50 emails.
We use Windows 2003/Exchange 2003 (SMTP)/Oulook 2003 Pro SP2.
This sender has not a send message size restriction.
Have you any idea which causes this issue and where can I look for it?