A lot of sex offenders have some condition of probation or release that requires them to have monitoring software set up on any computer they use.
So why not just use a fax machine instead? Anyone who wants to communicate with them can get one of those Internet-based fax numbers where you submit a PDF or whatever and it faxes it; and you can in turn receive such documents faxed to you via that number.
To keep these communications private, the sex offender can just throw sensitive correspondence into a Level P-4 crosscut shredder (which only costs like $200; if he's rich, then he can throw down for the Level P-7 shredder, which costs closer to $2,000). https://www.shrednations.com/2018/11/what-are-different-shredder-security-levels/
It's also handy if the SO has a fireplace, because he can just throw these documents into the fire if his probation officer knocks on the door, and achieve even greater security.
The fax machine can probably be configured to refrain from logging faxes, for additional privacy. When the probation officer is around, the machine can be disconnected from the phone line to prevent faxes from coming in during that time.
Anyway, by this means, sex offenders can ask their friends to google stuff for them, and receive the results via fax, and avoid having their every online activity screencapped. I suppose the phone company could be subpoenaed to see what activity has gone on via that phone number, and then the Internet fax company could be subpoenaed to find out who the customer is on the other end, but that's a lot of legwork and probably wouldn't be done just to catch someone committing a technical violation like associating with convicted felons; probably they'd only do that if criminal activity were suspected.
I've never heard of any sex offender having a condition of release regulating their use of the phone, fax, or mail (and it's not clear such conditions would be upheld by a court, since the real concern seems to be that predators will try to download CP or contact children by means of the Internet; I've never heard of a case involving trafficking, grooming, or seduction being done by fax), so I think this could be a pretty good loophole.
• ( https link ) How to Send and Receive a Fax Online