Smoothwall SWG is very suitable in companies where there is a lot of staff and power to distribute the bandwidth by areas and give priority to the staff that requires better service. It's also well suited for business that require protection of their data and services as it is constantly monitoring the network and does not let them enter dangerous sites.
Sophos Secure Web Gateway works perfectly for any SMB/Enterprise environment where the IT Admin wants to control the internet. With that said, I can not think of an organization that doesn't need to control or audit the usage of their internet.
Real-time IP filtering is very favorable. That helps limit and restrict prohibited content.
Elaboration of personalized reports of the activities or pages that users visit to make new blocking rules to the pages most visited by users that may damage the functioning of the servers.
Administrator Permissions: There's not enough granularity on the administrative side. We ran into an issue where we wanted to restrict junior admins from being able to see traffic per user. But in doing so, it also prevented them from adusting some other settings they had to have access to, like setting exceptions for sites.
CA Database: I occasionally run into issues where the list of certificate authorities in the appliance is not up to date, and I have to manually add a CA. These aren't rare, never-heard-of authorities, either, but they are usually subsidiaries of one of the major ones.
Feedback: Sometimes it takes some good detective skills to track down why a legitimate site isn't working. It's often because of content hosted elsewhere (images, for example), but the reports aren't always clear as to what actually gets blocked. It takes some trial and error sometimes to unblock something that should be okay for our business.
Smoothwall SWG has many tools similar to pfSense but in my opinion I like the graphical environment of smoothwall swg more. It is more didactic and simple to use for new users. Also pfSense lacks the tools for monitoring in real time and the elaboration of reports that helps to perform statistics on sites visited.
I had experience in the past with Barracuda and WatchGuard. Barracuda was fine, although I found it harder to configure and administrate. Less intuitive, but possibly more robust. WatchGuard was a nightmare, it either blocked too many things or not enough, and the rules were too complex. I would pick Sophos over either of these, both for ease of use, and for cost.
This software helps a lot and is very economical, since it is free and it can be installed in equipment with low performance. That is of importance to companies with little budget or who are just starting out in the market.
We have not had a single instance of malware since installing Web Gateway. We have other ways to prevent infections and attacks, of course, so this is just one tool in the box, but we had a handful before this from people visiting sites they should not have. Web Gateway has prevented those, at least.
There was some pushback initially as users had to deal with some business sites not working (usually due to CA problems). After the initial growing pains, however, we've seen very few other problems.
The appliance updates itself, in the middle of the night, so that reduces some overhead and planned downtime.