West Indies suffered a mini collapse as they reached tea on 502 for eight on the fourth day of the second test against South Africa in St Kitts on Monday.
Among the four first-innings wickets to fall in the afternoon session was anchorman Shivnarine Chanderpaul for a marathon 166.
The left hander faced 357 deliveries, compiling a modest total of 10 fours and one six, as he led the response to South Africa's 543 for six declared.
At tea, Ravi Rampaul was 10 not out and Sulieman Benn unbeaten on five.
Dwayne Bravo made a painstaking 53 in 215 balls as he and Chanderpaul ground out a partnership of 100 for the fifth wicket.
Chanderpaul was eventually caught and bowled by spinner Paul Harris, who also had Bravo snapped up by keeper Mark Boucher.
South Africa lead the three-match series 1-0.