Exchange 2013 with Outlook 2013 - Not getting pop-up or mail tips for attachments exceeding max size

Question

Our environment is Exchange Server 2013 CU3 and Outlook 2013 in cached mode. We have a transport rule that sets the max attachment size to 20 mb.
If someone sends an attachment larger than 20 mb they receive an NDR letting them know the message wasn't delivered because it exceeded the max attachment size. We would like for the user to be prevented from sending the message at all or to at least
get a mail tip before they try to send the message. The Outlook pop-up message that says "The file you're attaching is bigger than the server allows. Try putting the file in a shared location ..." isn't being generated for us. Not sure if that's
because we're running Exchange or not. If that pop-up isn't going to work it would be nice if the user could at least get a mail-tip warning them that the attachment exceeds the limit. But it doesn't look likes there's a mail-tip for attachment size, only
for message size. And, I've found that the message size mail-tip only works if the limit is set on the user. It doesn't seem to work if the limit is set via a transport rule.
Has anyone else gotten Outlook to present the pop-up or a mail-tip when exceeding attachment size? Any help you can offer would be greatly appreciated.

Answer 1

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.