Ever since the shock 2016 Brexit referendum sent sterling to its biggest one-day fall in decades, the pound has been see-sawing on differing perceptions of whether a deal will be done.
May told her cabinet on Tuesday that more time was needed to clear the final hurdle standing between her and a deal: the plan to ensure no hard border emerges on the island of Ireland.
Some of her senior ministers, such as Brexiteer Michael Gove, want to see the verdict of British government lawyers on how a post-Brexit plan for Northern Ireland's border might work. A Northern Irish political party, the DUP, which props up her minority government, wants the advice to be published in full.
There is only a slim chance that an agreement between British and EU negotiators can be reached in time to hold a summit of leaders in November to sign off the agreement, according to one British official.
May wants a deal - both on a withdrawal agreement and a framework for future ties - before year-end as she must get the deal approved by the British parliament. The EU holds a regular summit on Dec. 13-14.
"We are not there yet. The clock is ticking. The choices need to be made now on the UK side," EU negotiator Michel Barnier told reporters on Wednesday. "There are still important issues outstanding."
If May fails to clinch a Brexit deal with the EU, or parliament votes down her deal, then Britain would face leaving without a divorce deal, and thus without a transition period.
Many business chiefs and investors fear such a "no-deal" Brexit would weaken the West, panic financial markets and block the arteries of trade.