On Wednesday, TMZ reported that T-Pain’s production company, Nappy Boy Productions, is suing Lil Wayne’s Young Money Records for $500,000 over (you guessed it) non-payment.

The suit is just the latest in a long history of Cash Money-related claims of missing dough, dating back to the early 1990s. Adding to the complication is the fact that Wayne claims Young Money itself has been cheated out of tens of millions of dollars over the years by its parent company.

T-Pain is claiming that he never got paid for producing his 2008 collaboration with Weezy, Tha Carter III’s “Get Money.” He co-produced the track alongside Play & Skillz, and was told that he would receive royalties in return. The same goes for T-Pain’s artist Young Fyre, who produced “How to Hate” from Tha Carter IV. But no such royalty checks were forthcoming, and T-Pain estimates that between the two songs, his company is out half a million dollars.