PORTLAND, Ore. (KOIN) — A federal judge has found the City of Portland in contempt of an order restricting the use of less-lethal munitions during protests.

On Monday, U.S. District Judge Marco A. Hernandez concluded officers violated the temporary restraining order three times during a demonstration the night of June 30.

A crowd marched from Peninsula Park to the Portland Police Association building on North Lombard. Some businesses and the fence of at least one home were vandalized along the way. Police declared an unlawful assembly soon after the group arrived at the PPA.

At the time, a temporary restraining order was in place, restricting officers’ ability to use tear gas and less-lethal munitions as a way to disperse crowds where there is little or no risk of injury.

Attorneys for Don’t Shoot Portland argued officers violated the order nine times that night by launching tear gas, rushing protesters with batons, and firing impact munitions.

Judge Hernandez found three of the incidents were in violation of his order: When Officer Brent Taylor fired five shots from an FN303 (less lethal) launcher at the legs of a person who wouldn’t let go of a banner with a PVC-pipe frame; Taylor’s use of 10 more rounds from the FN303 against two people who were pulling another demonstrator away from police and back into the crowd; and when police fired less-lethal rounds at a person who was picking up an unknown object on the ground between demonstrators and the police line.

Some of the incidences Hernandez determined did not constitute a violation included using force against protesters who kicked smoke canisters toward police and one protester who successfully picked up a smoke canister.

Attorneys for the city argued the demonstration was dangerous for officers, with people throwing rocks, bottles, full cans of beer and soda, and smoke bombs at officers. Several officers were hurt that night and police arrested 29 people on charges ranging from disorderly conduct and riot to interfering with a police officer and assault on a public safety officer. The state is not currently pursuing charges against any of the people arrested that night, according to court records.

The decision follows a two-day hearing held in late October. Judge Hernandez will meet with both sides to decide what sanctions, if any, to issue.