Originally Posted by
SoCal App
Usual reason for mail stuck in the Outbox unsent is due to not being able to to connect to the SMTP server. Especially so if you tried to force the send and it still remained in the Outbox.
It might have been down temporarily.
Usual reason on a POP/SMTP service and Outlook, when the message appears bold but not in italics, is due to an issue with the addressing or (more rarely) a corruption within the message body or attachments.
Remedy is to check the recipients and re-hit SEND, then check for sending, and if the problem still arises then cut&paste the message body to a new email, address it and add attachments, and re-try sending.
If the above fails again, delve deeper into configuration issues, including telnetting to port 25 of the receiving SMTP server and manually sending emails using SMTP commands.