Thanks but I performed all of those trouble shooting prior to posting to the forum. But, I have found the answer!

After referring to this article;

http://technet.microsoft.com/en-us/library/bb124345(v=exchg.150).aspx

I removed the 10mb default limits from the organization config and chose to set the attachment and message size limits in our environment via transport rules instead. That is the only way you can actually set an attachment size limit.

I had read this article several times searching for an answer;

http://support.microsoft.com/kb/2813269#appliesto

The key is here;

"If you are using an Exchange Server account, the 20-MB attachment limit for Internet email accounts is not used by Outlook 2013. Instead, Outlook uses the limit that is configured on your Exchange server. To modify the setting that is used to control the size of a message that is sent through an Exchange Server account, follow these steps."

The steps that follow are for Exchange 2010 but they show setting organization limits not server limits. And note that it says the size of a message, not the size of an attachment. Since mail-tips for message size are not displayed when the limit is set via the transport rules I thought it was possible that the same inconsistency might apply to the attachment pop-up warning. I set the organization limits and voila! The pop-up now displays when an attachment that exceeds the message size limit is added to a message.

This is exactly what I wanted. Now users won't fill up their sent items trying to send large attachments that just bounce anyway.

It would be wonderful if Microsoft would provide information about what features of Outlook are affected when you apply message size limits at the various levels. 

• Marked as answer by Boudicca0308 Tuesday, April 08, 2014 4:51 PM

Thanks but I performed all of those trouble shooting prior to posting to the forum. But, I have found the answer!

After referring to this article;

http://technet.microsoft.com/en-us/library/bb124345(v=exchg.150).aspx

I removed the 10mb default limits from the organization config and chose to set the attachment and message size limits in our environment via transport rules instead. That is the only way you can actually set an attachment size limit.

I had read this article several times searching for an answer;

http://support.microsoft.com/kb/2813269#appliesto

The key is here;

"If you are using an Exchange Server account, the 20-MB attachment limit for Internet email accounts is not used by Outlook 2013. Instead, Outlook uses the limit that is configured on your Exchange server. To modify the setting that is used to control the size of a message that is sent through an Exchange Server account, follow these steps."

The steps that follow are for Exchange 2010 but they show setting organization limits not server limits. And note that it says the size of a message, not the size of an attachment. Since mail-tips for message size are not displayed when the limit is set via the transport rules I thought it was possible that the same inconsistency might apply to the attachment pop-up warning. I set the organization limits and voila! The pop-up now displays when an attachment that exceeds the message size limit is added to a message.

This is exactly what I wanted. Now users won't fill up their sent items trying to send large attachments that just bounce anyway.

It would be wonderful if Microsoft would provide information about what features of Outlook are affected when you apply message size limits at the various levels. 

• Marked as answer by Boudicca0308 Tuesday, April 08, 2014 4:51 PM

I'm looking for this prompt or warning when email is to large to send. I have two users that don't get this when sending over sized emails. Out of 40 Users I have only 2 that don't get this warning. Everyone else does get this prompt when sending. The email sends without warning but is deleted at the server without warning. So I need to know why these Users are NOT getting the warning. We host but not on an Exchange server. The Users are all setup as IMAP accounts and all on Windows 7 Pro Outlook 2013.

Did you check the registry entry as discussed in this article;

http://support.microsoft.com/kb/2813269/en-us

Yes but it doesn't apply in this situation. We have a 11mb size limit on our server and the default for Outlook is already 20mb. So the user trying to send the 14mb as an example should be getting the message from Outlook.

I did get this from the support people of the software we use.

If the sending agent (Outlook) supports this SMTP extension (ESMTP SIZE ), then MDaemon will determine the message size prior to its actual delivery and will refuse the message immediately. At this point, Outlook should have generated a delivery failure notification (using FROM address of Administrator@yourdomain.com).

If the sending agent does not support this SMTP extension then MDaemon will have to begin acceptance of the message, track its size periodically during transfer, and finally refuse to deliver the message once the transaction has completed (this may be why you are not seeing any notifications).

At any rate, the messages are refused, and MDaemon does not generate any notifications to the sender as RFC states that he sending agent is responsible for the NDRs.

So I am now trying to understand the ESMTP and if there are settings I can change to have Outlook send the message. The first paragraph above explains what is happening but they won't tell me how to fix in Outlook or if there is a fix. Any help on this would be appreciated.