Dean McDermott is once again facing jail time for failing to pay his ex wife.
Now Mary Jo, the mother of Dean's son Jack, 18, is preparing to take him back to court -- where a judge could order jail time, reports Page Six.
And this isn't the first time this has happened.
Back in March, Dean narrowly avoided jail time for failing to meet his obligations. He faced eight counts of contempt of court for failing to pay thousands of dollars in support going back to last October. He was read his Miranda rights before his ex withdrew the complaint (they privately worked out a new payment plan at the last minute).
Back in August 2015, Dean was also served papers after Mary Jo claimed he owed a significant amount of money for back child support for Jack, then 16.
"It's crazy that all this is over $1,500 [a month]. He could get a job at the Gap and pay that off every month," an insider told Page Six.
Dean, however, has denied the latest drama is over back child support. He took to the comments section of an Aug. 31 Instagram post to tell fans it's over delinquent alimony.
"My ex says it was for child support to make me look bad. I never missed a child support payment, and I paid for 12 years of private school and now I'm paying for his college and his rent," Dean wrote. "They don't mention that in the news now do they... There are 2 sides to every story. Unfortunately they don't tell my side."
Tori and Dean have made headlines for their financial troubles in recent years. In addition to Dean's support issues, he and Tori have failed to pay back taxes and have been sued by multiple creditors over unpaid credit card debts and bank loans.
In April, Page Six reported that the IRS had drained the couple's bank accounts, adding that in 2016, the couple were hit with a lien over $707,487.30 in unpaid federal taxes for their 2014 bill alone.
A source close to Dean told Page Six that he warned his ex his August payment would be late and that he made a payment on Sept. 1.
"It's not like it came out of left field," said the insider. "It was late because Dean was paying their son Jack's first-month rent, security deposit and several other college expenses, which Mary Jo would not contribute to."
On Aug. 19, Dean posted an Instagram photo of himself surrounded by purchases from Ikea he said were for Jack. "Getting Jack set up for College. Thank god for #ikea but it almost killed me!!! Now I have to set it all up!! I've definitely earned some #swedishmeatballs," he joked.
Amid Dean's money woes, he and Tori have been vacationing with their five kids at the luxurious Four Seasons resort in Punta Mita, Mexico.
Both have been posting photos from the trip on Instagram showing the children releasing sea turtles, getting their hair braided and posing for family photos.
"#selfielife in @fspuntamita #familyvacation #canwemovehere?" Tori captioned a pic of their whole brood on Sept. 1.
"With my 2nd to last baby watching the sun set in Mexico! I ❤️ this man so much. Proud of this guy that just turned 5. #finnfive @fspuntamita," Tori captioned another shot of herself and son Finn the same day.
After facing criticism on social media, Dean defended himself in the comments section of an Aug. 31 photo post, claiming he's "entitled to take my kids on a vacation before school starts."