Am 15.05.2013 um 20:46 schrieb "Mr. Parkis" <scottpar...@yahoo.com>:

> pfsense newbie here -
> 
> Is there a way to block users from sending attachments via webmail (HTTPS)  - 
> I do not want to block access to personal mail accounts. Just the ability for 
> users to send attachments via.
> 
> so all users can access their gmail, yahoo, aol, hotmail... or whatever 
> personal site they have (bluehost provided webmail account....)
> 
> they can send email but I would like to block attachments. Any way I can do 
> this


No.

Sorry for the short answer, but intercepting and filtering https-communication 
is not possible with pfsense (nor is it with most commercial software).
It is very difficult to lock down a network in such a way that no "undesired" 
packet leaves it.

There is for example software that will create a tunnel through your firewall 
just by DNS - it will be slow, but it will be enough to remote-control a 
workstation and transfer files.
It's professional pen-testers favorite tool to stump their clients...
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