For the third night in a row Thursday, demonstrations over the detention of a rapper accused of insulting the Spanish monarchy and endorsing extremist violence were marred by rioting.

The case of Pablo Hasél, who started serving a nine-month sentence in a northeastern prison this week, has sparked a raging debate about the boundaries of free speech in Spain and a political storm over the use of abuse by supporters of the rapper as well as the police.

On Thursday, the junior member of the governing coalition, the far-left United We Can (Unidas Podemos) group, filed a “total pardon” petition for Hasél and another rapper, Valtònyc, who fled to Belgium in 2018 to escape prosecution on charges of “glorifying” terrorism.

But court authorities in the northeastern region of Catalonia have announced that Hasél has lost a recent appeal and is looking at an extra 2 1/2 years in jail for obstructing justice and attack in 2017, possibly deepening the conflict. The sentence can be appealed before the Supreme Court of the country again.

The protests started Thursday, like the two previous nights, with major crowds in many cities that were, at first, largely peaceful.

“Hundreds sang songs in the regional capital of Catalonia, Barcelona, raping and shouting “Pablo Hasél, liberation! “and “Media from Spain, manipulators! ‘A barricade of garbage cans and a construction skip that blocked a major city street, hurling bricks, bottles and other items at riot police broke off the main party at a central square before hundreds.

As flames threatened to spread to surrounding buildings before firefighters arrived, there were moments of tension.

Police used batons to disperse demonstrators in the eastern coastal city of Valencia and detained at least eight people, according to the regional delegation of the Spanish government.

Nearly 80 people have been arrested and more than 100 have been wounded since Hasél was taken away from the university where he found asylum after refusing to appear willingly in prison.

The façades of the headquarters of many political parties were graffitied, a police station in the town of Vic was smashed, and shop fronts and bank offices in many cities, including the capital, Madrid, were significantly damaged by demonstrators.

An internal inquiry has also been initiated by the Catalan regional police to determine if one of their foam bullets struck a youth who lost an eye during the protests.

The rapper and his supporters argue that Hasel’s nine-month sentence violates free speech rights for writing a critical song about former King Juan Carlos I, and for hundreds of tweets that judges said glorified some of the deceased terrorist groups in Spain.

In addition to that case, the rapper has previously been charged with other offences or has pending assault trials, praising militant terrorist groups, breaking into private property and insulting the monarchy.

His legal situation has gained significant public attention since it comes after a series of other artists and social media figures have been placed on trial for breaching the 2015 Public Security Law of Spain, which was introduced and criticised by human rights groups by a previous conservative-led government.

Valtònyc, who has so far escaped extradition from Belgium, was one of them.

Parliamentary spokesman Jaume Asens of United We Can said the party had triggered the first move on Thursday to demand “urgent” and “total” forgiveness from both rappers. Pardons are a bureaucratic procedure that involve the final approval of the Spanish government, which is currently in the hands of Prime Minister Pedro Sánchez’s left-wing coalition and the Asens party.

And although both sides have agreed to change the criminal code to abolish jail sentences for offences concerning freedom of expression, after the opposition lambasted United We Can for not openly condemning the violent demonstrations, the protests have also opened the new rift in the fragile relationship.

A member of the center-left Socialist Party, Deputy Prime Minister Carmen Calvo, also denounced a United We Can spokesman who expressed support for what he called “antifascist protestors fighting for freedom of expression.”