Mostly your second answer. It can be regarded safe against most, if not all, non state level attackers, when used cautiously. If you use Tor Browser and HTTPS a

Mostly your second answer. It can be regarded safe against most, if not all, non state level attackers, when used cautiously. If you use Tor Browser and HTTPS and check how identifiable your browser is on https://panopticlick.eff.org/ https://panopticlick.eff.org/ you should be safe against employers, coffee shops, university administration and so on. At least as long as you don't make a mistake which reveals your identity (email reuse, etc) of course. It get's a bit more complicated for other services besides web browsing. torsocks works well to send traffic trough tor, but providing anonymity means you have to be really sure that no identity related information is leaked.