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The Israeli government failed to pass a bill that would extend legal protections to Israeli settlers in the occupied West Bank, a major setback that could collapse the fragile ruling coalition and create a legal conundrum in the territory, the Associated Press reported.

The vote would have prolonged an emergency regulation that has been in place in the West Bank since Israel captured it during the 1967 Six-Day War. The regulation creates a separate legal system for the half a million Jewish settlers there: It applies parts of Israeli law, both criminal and civilian, and allows for settlers to vote in elections, subjects them to compulsory military service and forces them to pay taxes to the state.

Three million Palestinians, on the other hand, are subject to another set of rules and have lived under military rule for six decades – a situation that human rights groups describe as “apartheid,” the newswire wrote

The regulations are set to expire at the end of the month and if they aren’t extended, it will create a legal quagmire for settlers and Palestinians.

The vote’s failure adds new headaches to the eight-party coalition of Prime Minister Naftali Bennett.

Made up of parties from across the political aisle, it was formed last year following four inconclusive elections in two years. The political union was created to oust longtime Prime Minister Benjamin Netanyahu and coalition members have been attempting to work out their differences to keep him out of power.

However, Monday’s vote underscored the deep divisions and weaknesses of the coalition, as well as creating a paradoxical situation in parliament: Opponents of the bill would vote for legislation in order to keep the coalition, while settlement supporters – including Netanyahu’s rightwing Likud party – would vote against it to derail the government.

While Bennett’s coalition is still standing, the situation has created further uncertainty about the union’s survival.