It might be fine if Dark Web stuff is popular in relevant countries such Russia, and the prospective spy can pretend that he was only trying to buy drugs or something, but I think the interesting thing would be to leverage mainstream websites, i.e. big things-- Google, news.bbc.co.uk, etc.
I guess the dark web has been fairly battle tested though by assorted criminal types. Normally it seems to just involve downloading tor browser and typing in an address.
When it was just used for drugs, yes, but when you have a war it's easy to switch to a mode where anyone whose internet connection involves possible Tor traffic is immediately arrested and shot within the hour.
This kind of thing apparently happened in Iran due to western intelligence groups making terrible and very obvious websites for communicating with them.
If you are somebody-- an expert at the Moscow radio-technical institute or drone designer or something it wouldn't be strange for the government to impose a 'no strange internet use, please, you understand why' and to enforce that brutally.
The way to do this right is to have something on big websites, and use SSL to hide what is being done. Cloudflare would also be a good choice. Computer games would be another reasonable choice.
It might be fine if Dark Web stuff is popular in relevant countries such Russia, and the prospective spy can pretend that he was only trying to buy drugs or something, but I think the interesting thing would be to leverage mainstream websites, i.e. big things-- Google, news.bbc.co.uk, etc.
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