This time, the actor is taking ex-wife Denise Richards to court, asking that his child support – which totals $55,000 thousand per month – be reduced, TMZ reports.
According to the report, Richards has been receiving the same amount since 2009, but since Sheen's income "has drastically declined," he can no longer afford to pay that each month.
Earlier this month, the former Two and a Half Men star filed court docs, obtained by PEOPLE, asking that his child support to ex-wife Brooke Mueller – who also receives $55,000 per month – be reduced for the same reasons.
In the paperwork, Sheen, 50, outlined his monthly expenses, revealing that he's gone from once making $613,000 per month to currently averaging $87,384 per month.
VIDEO: Denise Richards Knew Charlie Sheen Was HIV-Positive: Source
In an interview announcing that he was HIV-positive, Sheen also told Matt Lauer that he was extorted for $10 million by people threatening to make his diagnosis public. He also added in the documents that he spends about $25,000 per month on medical costs not covered by insurance.
"We came up with a number a long time ago and I had a great job and everybody was living large and that's not the case right now, but there's still that expectation to still keep paying this kind of money," Sheen told Dr. Mehmet Oz about the child support he pays to Richards during a February appearance on The Dr. Oz Show.
He continued: "At some point you just can't justify it, especially when there's no gratitude behind it. None. I would send somebody flowers every hour if I got that kind of dough tax free."