What began as a simple fee fight pitting Winston & Strawn against a former client—albeit one with nearly $500,000 on the line—has morphed into a technical dispute over what judges should do when a litigant misses a court deadline.

The U.S. Court of Appeals for the D.C. Circuit heard arguments on Thursday in Winston & Strawn’s lawsuit against James McLean Jr., who hired the firm to represent another individual, Edward Warneck. The firm says McLean never paid any of the bills, which totaled $494,760 by the time Winston & Strawn stopped doing work for Warneck in early 2013.

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