Legal scrutiny is growing against the City of Portland over its officers' excessive use of force against protesters.

Late Tuesday afternoon, lawyers representing Don't Shoot PDX urged a judge to find the City of Portland in contempt of court for violating a recent restraining order prohibiting police officers from shooting tear gas and other munitions at non-violent protesters. The court filing included three days' worth of examples illustrating how officers had violated Don't Shoot PDX's restraining order, which had been approved by U.S District Judge Marco Hernandez in early June.

Hours after Don't Shoot PDX's lawyers filed this request, Portland police officers again indiscriminately fired clouds of tear gas and impact munitions into a group of people protesting police brutality in North Portland. The restraining order specifically prohibits the use of either of these weapons against crowds containing peaceful protesters, unless lives are at risk.

"As you know, excessive force and pepper spray were used against people [last night]," said Teressa Raiford, founder and lead organizer of Don't Shoot PDX, during a Wednesday press call. "We felt that by bringing this lawsuit forward, it would stop this force."

Last night's actions by police showed otherwise.

According to witness accounts, protesters who had marched from Peninsula Park to the N Lombard headquarters of the Portland Police Association (the city's rank-and-file police union) were immediately met by a line of aggressive officers dressed in riot gear. According the Portland Police Bureau (PPB), that's when several protesters began tossing empty water bottles, cans, and rocks towards the armored cops. Oregonian reporter Everton Bailey also observed that several fireworks were shot into the air by protesters, but added they were "fizzling out" on the ground between officers and protesters.

PPB officers responded to this action by shoving the crowd and shooting "less lethal" munitions directly at people. Not long after, PPB declared the scene was a "riot" over loudspeakers and ordered everyone to leave the area. Within minutes, officers began shooting tear gas into the remaining crowd of a hundred people. Neighbors who came outside to observe the police, people working at nearby businesses, and those driving through the neighborhood were also impacted by the plumes of chemical gas.

The evening ended with officers arresting a number of protesters and journalists on charges, including interfering with a police officer, resisting arrest, disorderly conduct, and assaulting a police officer.

Jesse Merrithew, an attorney representing Don't Shoot PDX, told reporters Wednesday that the police are violating the US Constitution by continuing to use force against members of the public who are peacefully expressing their freedoms to protest.

"The Portland Police Bureau does not respect civil disobedience," said Merrithew. "They are intent on enforcing their rules with force. Not by arresting people and allowing a judge to decide what’s right or wrong, but by beating them."

Judge Hernandez has yet to respond to Don't Shoot PDX's contempt of court request. Merrithew said his legal team will update the request to include details from Tuesday evening's PPB response.

"The court has broad discretion over how to enforce their order," said Merrithew. "We’re hopeful that the court will see the imperative nature of doing this quickly."

Don't Shoot PDX filed its initial lawsuit after Portland City Council declined to ban PPB's use of tear gas on members of the public. On Wednesday, Merrithew said he was thankful that other politicians—like Oregon House Speaker Tina Kotek—have spoken out against PPB's lack of restraint and called on Wheeler to address the abuse.

"We’d like all of our public officials to speak out about this," said Merrithew. "It is a mystery to me that City Council didn’t acknowledge the violence that was perpetuated last night during today's City Council meeting, and the seeming lack of control they have over our police department. You see this on video, you know it's wrong, you have an obligation to say something."