Judge Emmet Sullivan of federal district court in Washington, D.C., was not prepared on Wednesday to rubber-stamp the $298 million settlement between Barclays Bank and the Justice Department to resolve allegations the bank violated government sanctions in processing financial transactions with countries that include Cuba, Iran and Sudan.

Sullivan of the U.S. District Court for the District of Columbia pressed the Justice Department about why no individuals — and no person from senior management — was being held criminally liable for the actions of the London-based bank. Sullivan called the charges “shocking.” But at the end of a hearing that lasted more than an hour, Sullivan approved the deal.