AjM said:
There is no error message. Sometimes mail will go, other times it won't.
There's probably something I'm missing.
This problem is why I switched to Outlook Express in the past.
This seems to only occur when I attempt a reply to an e-mail.
If there were no error dialogs, Outlook got no errors from connecting to and
using the mail server specified in the e-mail account(s) defined in Outlook.
Turn on the troubleshooting log to see if you can any errors (but if there
were any then you would've seen an error dialog).
Send a test mail using Outlook and another using Outlook Express. Send them
to a webmail account, or use the webmail interface to look at the mails
instead of a local e-mail client. Compare the headers to see how they
differ (not necessarily by order but what headers are present or missing
between them).
Are you using a template in Outlook (or in Word used as the e-mail editor)?
Could be you are sending LOTS of e-mails with the same template, or other
users are using the same background or template, and your mail server's
anti-spam solution sees them all as essentially the same or nearly the same
message and figures according to the volume that they are spam.
What happens when you disable the e-mail scanning feature of your anti-virus
program?