> You think surreptitiously spying on a child’s rule-breaking online activities is a better parenting approach than direct conversation about what’s going on?
Please show me halochos that say that being direct with people is always the right thing to do.
Kids are also people … So, if direct conversation works – gezunte heig. But let’s say the parent tried it 3 times already and the kid just evades it, gets a different VPN, for example (kids don’t read this). Then, yes, let them have their innocent fun and monitor for the signs that something bad is happening. Are you afraid that this violate R Gershom herem on reading letters? Then, just monitor IP addresses or inform the kid electronically as businesses do: “this device (network) is subject to monitoring”.