Has been working fine for a year...

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Outlook version
Outlook 2013 32 bit
Email Account
I've been using an MS Outlook 2013 account (32 bit, Professional; Windows 7) just fine for a year and it has suddenly stopped sending emails on a POP3 account with MS Word attachments of about 2MB and larger. The thing is, the other email accounts on the same instance of Outlook, including two other POP3 ones, are working just fine. Some additional oddities:
  • The emails go in my Sent folder but the receiver does not get them (tested on multiple recipients; true);
  • The emails send fine from the web service back end, so the issue does indeed appear to be with Outlook itself;
  • Attachments under ~2MB go through just fine; and
  • The file format appears to matter -- only MS Word documents as attachment are not making it through (well, at least large size PDFs and large MS Excel workbooks are making it out properly).
I'm uncertain what may have occurred in the past week. No new programs installed. Thoughts? I've disabled all the .COM add-ins and tried safe mode (yes, lots of closing and re-opening Outlook, too). I'm starting to lose my mind here... Help, please?
What antivirus software do you use? Problems sending larger message is often caused by an antivirus scanner - its takes too long to scan larger attachments and the send times out. It sometimes helps to increase the time out, but honestly, you don't need to use an antivirus scanner on outgoing email. (Or on incoming mail for that matter.)
Diane: Thank you for your response. I'm using Norton Security Suite. I disabled the outgoing email scan (which hadn't previously posed a problem, nor is it affecting my other Outlook accounts) and, regretfully, the same issue still stands. Additional thoughts?
I assume all large attachments, not just email, is affected? Are you sending from word or Inserting the attachment in Outlook? Can the other account send large messages? If so, it could be the server - try changing the time out in File, Account Settings, double click on the account. Click More Settings then Advanced tab to increase the timeout.
Only MS Word documents ~>1.5MB attached to emails crafted in MS Outlook are affected. This is specific to just one POP3 account within Outlook; the other POP3 accounts are operating just fine. I increased the timeout to no effect.

Emails post to the Sent folder in less than 30 seconds (before and after the adjustment above).

The issue remains...
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