The fall of Damascus over the weekend brought a dramatic end to the Bashar Assad regime’s 24-year rule over Syria — and now deprives North Korea of one of its most important partners in the Middle East.

Rebel groups led by the armed group Hayat Tahrir al-Sham (HTS) seized control of the capital on Sunday after sweeping through the country in less than two weeks, with the Syrian leader reportedly fleeing to Russia aboard a private jet.

While incumbent Prime Minister Mohammed Ghazi Jalali will lead Syria until a new government takes charge, Assad’s exit creates headaches for North Korea.