Byju's executive Vinay Ravindra and ally Rajendran Vellapalath face $25,000 daily sanctions for contempt of US court.
Delaware federal judge found they failed to explain their role in stripping assets from Byju's US businesses under court supervision.
Vellapalath's company Voizzit violated court order by attempting to seize Epic! Creations and Tangible Play assets through Indian lawsuit.
This marks the third time a US judge found members of Byju Raveendran's inner circle violating court orders in the $1.2 billion lender dispute.
Previous sanctions involved Raveendran's brother Riju Ravindran and hedge fund founder William Morton over $533 million missing loan proceeds.
Judge Brendan Linehan Shannon noted these contempt circumstances as "certainly rare" in US bankruptcy court.
US lenders seek to liquidate Byju's US education software companies purchased for $820 million.
Indian business court restored lender agent Glas Trust Co. to the creditors committee, ordering investigation of their previous removal.
Vellapalath claimed from Dubai that Voizzit owns Epic! and Tangible Play due to $100 million loan to Byju's, deemed "not credible" by judge.
Once valued at $22 billion, Byju's faced legal troubles after its US arm filed for bankruptcy following allegations of hiding $500 million.