In a good sign he's hardly planning to rubber-stamp Portland's police reform settlement agreement with the US Department of Justice, US District Court Judge Michael Simon on Friday submitted a detailed—and difficult—list of questions to the four main parties in the case: the city, the feds, the Portland Police Association, and the Albina Ministerial Alliance Coalition for Justice and Police Reform.

Read together, they show Simon was listening intently to outraged community members during a day-and-a-half hearing last month on whether the proposed settlement is fair and reasonable. And they show he's serious about getting the city, the feds, and the police union to consider making changes in light of that testimony. Simon—tasked with deciding either to approve or reject the deal—was politely rebuffed at the end of that so-called "fairness" hearing when he asked if either of those parties maybe needed some time to prepare, submit, and haggle over amendments.

It's possible if he doesn't like the answers he's looking for, or if his questioning doesn't produce changes, he'll reject the deal. In 13 questions entered into the court file Friday, Simon touched on some of the most controversial flashpoints in the agreement.

He reacted to the revelation that planned mental health crisis centers are merely "aspirational," a subject the Mercury explored after the hearing. He's asked the parties to explain why the volunteer board that hears appeals in police misconduct cases will only have 21 days to do its work.

He's probing for creative ways to expand his own oversight of the deal, provided he accepts it. He wants to know why officers haven't be required to wear body cameras. He also has asked for an explanation of why police officers need 48 hours, in cases when criminal charges aren't pending, to discuss a force incident detectives as part of an internal review.

Dan Handelman of Portland Copwatch says he sees the judge's questions as a means of triple-checking with the city, police union, and feds about whether they really and truly don't want to seek a few changes that might address community concerns.

"He's asking them, 'are you sure?'" Handelman says. We really want to see those changes made. But it's nice he's going to at least force them to respond."

It's a short document, which you can review here (pdf), and it's worth looking at. When the parties head back to court later this month, the answers could be a decent roadmap to his decision.