Alexandria, VA (CNN) A federal judge on Thursday questioned whether there was enough evidence to uphold two guilty verdicts in a foreign lobbying case that stemmed from the Russia investigation and ensnarled a business partner of former Trump aide Michael Flynn.

At a procedural hearing in the Eastern District of Virginia, federal Judge Anthony Trenga grilled the prosecutors who successfully took Iranian-American businessman Bijan Kian to trial this summer. Kian was convicted of illegally acting as a foreign agent and conspiring to hide his work from the Justice Department — fallout from pro-Turkey lobbying he did with Flynn in 2016.

The judge repeatedly asked tough questions and pressed prosecutors for details proving that the Turkish government was "directly involved" in Kian's lobbying campaign and said some evidence presented at trial suggested there was "a lack of direction or control" by Turkey. The judge's questions got at the core tenets of the foreign agents laws that are in play in this case.

Defense attorney James Tysse said "no reasonable jury could ever conclude" that Kian was directed by Turkey and urged Trenga to toss both convictions or, at the very least, order a new trial. Trenga said he'd make a ruling "as soon as I can."

Sentencing is scheduled for October 18.

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