On Sunday, a northeast Minneapolis resident raced to the site a few blocks from his house where masked men with federal agent patches put someone inside a black van. 

The resident, Ethan — who declined to give his full name for publication, citing fear of reprisal — began to record on his phone. Then an agent came around to the side of the van, yelled at Ethan to move, and at the same time doused his eyes with orange-colored pepper spray. 

In the world Minnesotans are now living in, incidents like those have become common — and they also raise questions about whether they violate legal observers’ constitutional rights.

Katherine Menendez, a Minnesota federal judge, issued an 83-page ruling last Friday that specified a number of actions that federal immigration agents cannot do, because it would violate onlookers’ First Amendment rights. One such tactic is “using pepper spray or similar nonlethal munitions and crowd dispersal tools against persons who are engaging in peaceful and unobstructive protest activity.”

On Wednesday, a federal appeals court paused Menendez’s ruling for now as Trump administration lawyers and American Civil Liberties Union-Minnesota attorneys representing demonstrators and observers prepare to argue the merits of their respective sides. 

There are conflicting accounts about whether the six-day window in which Menendez’s order was in effect influenced federal immigration agents’ behavior. Here is a look at the intersection between court rulings and reality.

What do I need to know about this lawsuit and other legal action?

The ACLU lawsuit was filed in December on behalf of six named complainants, and all protestors and observers present in the Twin Cities during Operation Metro Surge. 

The lawsuit includes discussion of larger free speech issues and alleges that ICE is performing unlawful searches and seizures in Minnesota. But the lion’s share of the case delves into the nitty-gritty of ICE tactics. 

Menendez’s order states that “a variety of [ICE’s] conduct would chill a person of ordinary firmness from engaging in further protected activity.”

“That conduct includes the drawing and pointing of weapons; the use of pepper spray and other non-lethal munitions; actual and threatened arrest and detainment of protesters and observers; and other intimidation tactics,” Menendez wrote.

Federal agents also cannot stop drivers and passengers in vehicles without reasonable suspicion that they are interfering with the agent’s work. 

Related: Free speech advocates see a pattern as ICE protesters, observers face violence in Minnesota

“The act of safely following [agents] at an appropriate distance does not, by itself, create reasonable suspicion to justify a vehicle stop,” Menendez wrote. 

The order was always likely to be temporary, as the lawsuit is still in its early stages. Menendez  made her decision based on declarations and evidence submitted to the court from both sides, rather than an evidentiary hearing.  

In appealing the judge’s ruling, the Trump administration said Menendez’s specific orders were not specific enough. 

The judgment was “replete with vague terms that DHS officers must interpret and apply in dynamic and dangerous law-enforcement situations under penalty of contempt,” the administration wrote in legal filings.

The federal government argued protesters and observers had been unable to prove their constitutional rights were violated. Any broader pattern of misconduct by officers as part of Operation Metro Surge is “meritless,” they argued.

The ACLU case is not the only game in town. There are several pending lawsuits including one filed by Minnesota Attorney General Keith Ellison that argues ICE is violating state sovereignty and should leave Minnesota entirely. 

Did this order — or other lawsuits — change ICE agents’ behavior toward observers and protesters?

The reports are mixed. 

Part of the ambiguity comes from Department of Homeland Security Sec. Kristi Noem, who said on CBS’s Face the Nation Sunday that the judge’s order “didn’t change anything.” 

Noem called the decision “a little ridiculous,” arguing that ICE does not partake in any activity banned by Menendez. When shown a video of a Minnesota family getting pepper sprayed, Noem pivoted to stating that federal immigrant agents are subject to increasing militance and obstruction from protestors. 

Earlier on Wednesday, state Rep. Mohamed Noor, DFL-Minneapolis, said at a press conference, “We’re seeing violations of the order from the judge. As I speak with you right now a gentleman from St. Paul was pulled from his car who is a U.S. citizen.” 

Noor said that ICE had stopped this person without reasonable suspicion.  

Related: ‘My eyes were stinging’: The chemicals used by ICE when they confront observers

However, William Stancil, a Minneapolis-based attorney, who has continually filmed ICE agents since the death of Renee Good, said that — from what he has seen and heard — interactions between agents and onlookers were dialed down after the federal court order. 

Stancil, though, speculated that ICE agents got the message Wednesday afternoon that the order was void. 

“They have been incredibly aggressive,” Stancil said as he observed agents in south Minneapolis. “I was tear gassed twice [this afternoon].”

Stancil provided several videos of ICE behavior from Wednesday. In one, ICE enters a house in the Whittier neighborhood as protestors across the street yell “Do you have a warrant?” and “Can you even spell warrant?”

Then — in freezing weather — a quartet of armed-agents exit the house with a shirtless brown-skinned man wearing nothing but baggy blue shorts and a red-plaid towel over his shoulders. 

The onlookers cry out with expletives at the agents, before the agents approach and the video stops. 

What power do courts have to make ICE follow a judge’s order?

There does not appear to be a clear precedent for what is happening in Minnesota. In Illinois, for example, ICE demonstrators scored a preliminary victory in a similar case regarding agent’s tactics. ICE successfully appealed, then action on the case effectively died out when federal immigration agents left Chicago en masse. 

In theory, a judge could find ICE or individual agents in contempt of court, which could include monetary penalties and prison time. But the Department of Homeland Security is not your garden variety civil court defendant losing in a child support payment or lost wages dispute. 

“In practice, we’ve seen the Trump Administration get away with a lot with these federal judges because the judges want to avoid the appearance of partisanship or are afraid of drawing even further ire from Trump’s supporters,” said Peter Larsen, an assistant professor at Mitchell Hamline School of Law. “For Minnesota, whatever the outcome, it’s very likely that we will see delays in compliance from the Trump Administration and appeals of final judgments in the District Courts up to the Court of Appeals and Supreme Court.”

In the meantime, ICE observers may have to police their own safety.

“If he had given me a warning, I would have heeded that right away,” Ethan in northeast Minneapolis said of his encounter with an ICE agent. “I have a family. I’m not interested in getting shot, like Renee did.”

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