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Citing his cooperation ahead of his initial sentencing in December 2018, prosecutors did not push for prison time. At the sentencing, he decided to postpone the proceeding so he could testify against a former business associate, Bijan R. Kian, in hopes of getting the most lenient punishment possible.

But Mr. Flynn’s cooperation took a stark turn. He fired his well-respected lawyers and hired Sidney Powell, a truculent former federal prosecutor, who embraced right-wing conspiracy theories suggesting Mr. Flynn had been a target of a politically biased F.B.I. cabal and accused prosecutors of misconduct in his case.

Mr. Flynn then changed his story on the eve of Mr. Kian’s trial, where Mr. Flynn was critical to the government’s case. Though a jury convicted Mr. Kian, a federal judge later threw out the charges, saying prosecutors failed to make a strong enough case. Mr. Flynn “ultimately hindered their prosecution,” according to the government’s sentencing memo.

And Ms. Powell asked a judge to dismiss the charges against Mr. Flynn.

The efforts were risky and possibly self-defeating, and Mr. Flynn’s gambit ultimately failed. Judge Emmet G. Sullivan rejected Mr. Flynn’s many claims against prosecutors late last year, effectively ending his chances of getting his conviction thrown out, something his supporters had hoped would happen. Still, some hope that Mr. Trump will pardon Mr. Flynn, whom the president has said was treated badly.

Mr. Flynn’s lawyers, led by Ms. Powell, say he has fully cooperated with the government.

But in their memo, prosecutors pointed out his “apparent failure to accept responsibility” and “his failure to complete his cooperation in — and his affirmative efforts to undermine” the trial of Mr. Kian, who was charged with violating foreign lobbying laws.