Yes, if even the simplest obfuscation technique is employed, this system falls flat on its face. (Shh don't tell the regulators)
https://www.bluecoat.com/products/dlp
“Blue Coat DLP allows you to easily create policies that analyze the data source, content, destination and more.
…
accurate data “fingerprinting” capabilities, in addition to powerful keyword, pattern, and regular expression support, so you can create precision policies to effectively secure your data while minimizing false positives.”
Sure, the every HN reader might have questions about this but I'd bet a LOT of C-level executives are receptive to this.
I certainly agree that if you have a requirement to watch outbound data like this, having a system to selectively capture it is much better than simply attempting to record everything.
Notes:
1) Modern DLP solutions have some pretty sophisticated obfuscation detection tech. Like almost all of these kinds of technologies, they're looking for the 80% case, not the 99% case.
2) Tunneling out encrypted tunnels is subject to traffic analysis techniques. It's not as uncommon as one might suspect to detect out-of-band ex-filtration of many different types this way.
Automatic analysis to statistically detect hidden channels is a research topic, it can be used to put bounds on the exfil rate but not reliably detect it.
Yes, but what are those controls? You check every packet to see if it contains any information from one of your databases?
What if the person sending the data just applies a simple obfuscation technique to the data, or just tunnels through some other encryption scheme?
Edit: downmods? really?