https doesn’t completely hide the destination, only the contents. And if he was using https to connect to a site purely for the purposes of obfuscating activity

https doesn’t completely hide the destination, only the contents. And if he was using https to connect to a site purely for the purposes of obfuscating activity, that would probably be squashed under the same rules. If he was using an encrypted remote drive to communicate with others that would also be a breach. You can’t “well, technically” your way out of obvious breaches of clear court instructions.