England opener Rory Burns was bowled for 84 by spinner Roston Chase just before lunch on day four as West Indies inched closer to victory in the first test in Barbados on Saturday.
The dismissal left England, chasing a record 628 for victory, on 134 for two. The home side have five sessions remaining to wrap up the match at the Kensington Oval in Barbados.
Burns had barely been troubled by the four-pronged pace attack but off-spinner Chase got the breakthrough in his first over of the day by finding an opening between bat and pad.
Burns had earlier lost opening partner Keaton Jennings for a patient 14. Jonny Bairstow was not out on 29.
After rattling through England for 77 in the first innings, the home team found the going considerably tougher second time around, with the visitors seeing off the new ball without fuss.
It was not until the 29th over of the innings, and the ninth of the morning, that West Indies finally broke through.
Alzarri Joseph, in his first over of the day, induced Jennings to drive outside off stump and get a thick edge to captain Jason Holder, who took a sharp catch at second slip.
Jennings faced 84 balls, having helped see off the new ball in a partnership of 85.
Bairstow might have gone for a golden duck had the fielding team had a short leg in place for what would have been a simple catch. But Holder had set an inexplicably defensive field for the new batsman and the opportunity went begging.
England had resumed on day four at 56 without loss.