Updated 8:43 p.m. | A politically connected contractor made a $500,000 contribution this spring to a pro-Trump super PAC the day after it received a payment of almost the same amount as part of a Department of Defense contract, a watchdog group said.

The Campaign Legal Center flagged that contribution and a $50,000 contribution from another company to a super PAC supporting Florida Gov. Rick Scott’s Senate campaign, in separate complaints to the Federal Election Commission filed Wednesday afternoon.

The donations represent rare violations of a 75-year-old ban on campaign contributions from federal contractors, said Brendan Fischer, director of the federal reform program at the Campaign Legal Center.

“This seems like a brazen violation of well-established law,” he said. “It’s possible that both of these entities are ignorant of the federal contractor ban. But it’s also possible that they expect that they can make large contributions to fed super PACs and get away with it because the FEC has been so reticent to enforce the law.”

Federal campaign finance law prohibits companies that are bidding or hold contracts with the federal government from making federal political donations. Individuals can make unlimited contributions to super PACs.