I hate asking questions like this, because I always worry I missed something simple.
I have, several times, setup a simple pfSense install, and every time something in pfSense steps in and kills the sending of attachments in GMail over a certain size (~400k+). Now, to head off the “pfSense can’t do that” comments, yes it can. I have the same issue on a base install, on an install with or without Suricata/Snort, with or without Squid, etc… However, I have never had this problem (on the exact same box on the same network with the same attachment(s)) with Untangle, OPNSense, ipFire, Sophos, Meraki MX, etc…
There must be a simple switch I am missing somewhere, but it is driving me up the wall. I really want to swing a lot of sites over to pfSense but this is a deal breaker.
Any concrete advice would be greatly appreciated. This issue seems to have been around for awhile, but the fixes seem to be extremely varied (depending on version).
I am running the latest stable version.