Alastair Cook ended his two-year wait for a Test hundred, but the England captain fell to the last ball of the day to ensure West Indies hold the upper hand in the third Test.
Cook had not hit three figures since May 2013 - a drought of 36 innings - but appeared back to somewhere approaching his best on day one in Bridgetown before falling late on for 105 to Marlon Samuels.
The England skipper let out an exclamation of relief when bringing up his ton with a four off Shannon Gabriel (2-36), but his joy was short-lived as he attempted to cut Samuels and edged to Denesh Ramdin with just five balls remaining.
That brought about a slightly early finish, and the Windies are sure to be thrilled with a day in which they reduced England to 240-7 after Cook won the toss and elected to bat.
Jonathan Trott's difficult tour continued when he went for zero - the 34-year-old's third duck of the series - in just the second over when he meekly played a Gabriel delivery straight to Veerasammy Permaul.
While Trott has struggled in the Caribbean, Gary Ballance (18) has flourished and he looked in good touch once again before having his middle stump uprooted by a fine Jason Holder (2-34) inswinger.
Ian Bell (0) followed soon after - caught and bowled by Holder - and England were toiling at 38-3 in the 18th over.
The in-form Joe Root steadied the ship alongside captain Cook, with that duo steering the tourists to the lunch break without any further casualties.
But when Root (33) nicked Permaul behind to Ramdin soon after lunch, West Indies were firmly in control.
However, Cook continued to play with typical assuredness and - while being ably assisted by Moeen Ali (58) - to lead England to 151-4 at tea.
Moeen brought up his half-century in style with a slog-sweep six off Samuels, but was run out soon after when Cook tried to run a single that was simply not on.
Ben Stokes was next to give his wicket away cheaply, the all-rounder starting well to get to 22 before playing a sloppy shot to give Gabriel his second wicket of the day and leave England 233-6.
Stokes' dismissal ratcheted up the pressure on Cook even more, with the skipper on 98 at the time of his dismissal, but he calmly clipped Gabriel to midwicket to finally claim his 26th Test century.
But Cook will be frustrated with the manner of his dismissal, which means West Indies head into day two on top.