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Yep, pretty sure it's easier these days with machine learning and voice recognition. Back in the day it was loads of manual labour.
There's old and story that when my grandfather was being watched, they returned home one day, earlier than they should've and found somebody sniffing around in their apartment. The person escaped climbing to a balcony of another flat. Then they knew the KGB was on to them.
I've got a friend from Belarus who is advised not to return just in case they've got something on him. He hasn't been home for more than 3 years even though his family lives 100 km from Vilnius.
It's funny we have memes about FBI spying on us through our front cams but there's slight difference - we don't risk going to jail even if we're actively anti government.
The beauty of democracy. Which is also a double edged sword when freedom of speech is absolute but it's another issue.
I know people with family in Russia who tell me that their relatives have been told their phones and internet use were being monitored by the FSB to ensure they're not anti-government. The name of a lot of the instruments of oppression have changed, but the methods haven't; they've just modernised.