Appeal to basic human envy and greed. Give small shiny gifts to whoever has access to the west. Fund smuggling operations, assist in setting up black markets.

Appeal to basic human envy and greed. Give small shiny gifts to whoever has access to the west. Fund smuggling operations, assist in setting up black markets. Send in films and the means to play them. Doesn't matter if they get taken away from the people you give them to, so long as someone over there ends up with them. No need for overt propaganda. Simply, "here are shiny things, here are people enjoying shiny things, everyone else has this stuff and you don't." And, more basic level: "see how people can live, what can be taken for granted. Food. Light. Toilet paper. Supermarkets." Then wait. They'll overthrow the regime themselves. It worked for the Soviet Union, though it took a while. It'll work here, too.