Fifty-four years ago, one of the most suspicion-wracked and contentious international relationships (next to the U.S.’s with the Soviet Union) heated up when the United States and Cuba ended formal diplomatic ties and closed their embassies in Havana and Washington D.C., respectively.

The years following the break were marked by accusations of sabotage and attempted assassinations, proxy wars, and nuclear near-misses. That icy tension thawed a bit on Monday, July 20, 2015, if not completely, as both nations have opened their embassies once again. This news comes on the heels of renewed diplomatic talks and the lifting of embargoes and a decades-long travel ban.

The diplomatic dance has begun anew, and for those in the intelligence community, there are sure to be mixed feelings. Although access to the country has eased, lingering questions, concerns, and doubts, given our history, likely remain.

So after almost 55 years of trying to penetrate the inner workings of the tiny island that has proved to be a big policymaker nightmare, how might past events stack up for or against future U.S. intelligence operations in the region?