That isn't my impression of how the web works. The second your bits leave your LAN, they begin traveling over infrastructure that is owned and operated by another private entity. They could rescind your access at any time, especially if the government orders it so.
Eh, TikTok could set up some proxies on non-China non-US controlled shared infrastructure, and with modern https the US network carriers wouldn't be able to tell if the traffic was to them or someone else. The degree in invasiveness needed to enforce this policy via ISPs (prohibiting effective encryption) would probably end up violating the first amendment.
1. TLS is not the impenetrable black box it is made out to be. Every year there are about three papers published at the top tier computer security conferences about identifying applications within TLS. Check out the NDSS proceedings.
2. The EO prohibits conspiracies to evade the ban. This means anyone caught knowingly helping to evade the prohibitions would be subject to legal penalties.
1. Yes - but a law requiring US carries to perform cutting edge research to detect who you're talking to is... unlikely. It's also much more likely to violate the constitution than a law prohibiting trade.
2. Sure, but the entities involved in evading the ban wouldn't be US entities.