At midnight, the group set off for the flagpole with a namesheet with contact information (pirate names of course). When we arrived, the flagpole was inaccessible because the access hatch which allowed us to lower the flag was locked shut. Although we immediately wanted to abandon this, AndreyShur produced a lockpick, and the plan went along. However, it was not until 30 minutes later did we open the hatch and lower the flag. We briefly checked that the flag was upright, and then raised the pirate flag just under the American flag.
What was interesting afterwards was that AndreyShur noticed that we couldn't close the access hatch properly without picking the lock again, so it would have been the first instance in which a lock was picked in order to lock it.
Unfortunately, there was no wind the next day.