Hopes of a Brexit deal appeared to fade early Thursday (October 17).
Northern Ireland's Democratic Unionist Party said it could not support last-ditch proposals put forward by Prime Minister Boris Johnson and the European Union.
A serious blow to the PM just hours before the bloc's leaders meet at an EU summit.
In the run up, negotiators have been working night and day to reach a compromise on the Irish border issue.
But DUP leader Arlene Foster named three sticking points - customs, consent and VAT issues.
Johnson is trying to strike a Brexit deal at the summit that could allow the UK to leave the bloc in an orderly manner on October 31st.
But patience is running out.
(SOUNDBITE) (English) EUROPEAN COMMISSION PRESIDENT JEAN-CLAUDE JUNCKER, SAYING:
"Ladies and gentlemen, dear friends. I'm obliged to express myself in English, I don't know why, because everyone understands English, but nobody understands England."
Juncker's words in Brussels on Wednesday a sign of the exasperation felt at negotiating Brexit.
But some hope given by German Chancellor Angela Merkel on Thursday when she said a deal is still possible, but there's still more work to do.
(SOUNDBITE) (German) GERMAN CHANCELLOR, ANGELA MERKEL, SAYING:
"There has been movement in recent days, significant movement. The British side has shown a willingness to negotiate and underlined this with very concrete proposals. So we are on a better path than before but, today I must say very clearly, we have not reached the goal yet."
If Johnson agrees a deal he could put it to UK parliament on Saturday (October 19).
He'll need 320 votes to get it ratified.
If that fails - another delay could be on the way.