India was left with the herculean task of chasing a world record 420 after England refused to declare in an unfocussed second innings, cut short by Ravichandran Ashwin's brilliance on a sharply turning fourth-day strip in the opening Test here on Monday.
At stumps, India were 39 for one, requiring another 381 runs to set a new record and take a 1-0 lead in the four-match series. The previous best is 418, chased by West Indies against Australia in 2003.
Relishing bowling on a responsive pitch, the seasoned Ashwin returned excellent figures of 6/61 to snap England's second innings at 178 after the home team conceded a massive first-innings lead of 241 runs.
With opener Rohit Sharma (12) back in the hut, Shubman Gill (15) and Cheteshwar Pujara (12) will begin the proceedings for India on the fifth and final day at the MA Chidambaram pitch, which has started to play tricks.
India would have been in a bigger hole had it not been for a seventh-wicket partnership of 80 runs between newcomer Washington Sundar (85) and Ashwin, who also contributed a 31 with the bat before picking his career's 28th five-wicket haul.
But despite the duo's best efforts, the hosts still fell way short of the follow-on target after being bowled out for 337. India resumed the day at 257 for six.
Hoping to give their bowlers some respite from the sweltering heat, England decided against enforcing the follow-on and batted again.
But the start wasn't the one they wanted as Ashwin bowled his off-spinners to deadly effect with the new ball, the bounce aiding him in his endeavour.
Ashwin removed Rory Burns with the very first ball of the second innings when he induced an edge for Ajinkya Rahane to take an easy catch in the first slip.
Having ambled to 16 off 37 balls, Dominic Sibley was shown the door by Ashwin, with the bounce again helping the off-spinner.
Veteran pacer Ishant Sharma was rewarded for bowling with a lot of hearth throughout the match when he had Daniel Lawrence trapped in front of the wicket with the one that snaked in.
That was wicket number 300 for Ishant, making him the sixth Indian and third pacer from the country to reach the landmark.
Ben Stokes could not replicate the form of his first innings as he played away from his body to give Rishabh Pant a catch off Ashwin.
As wickets kept falling at one end, skipper Joe Root (40 off 32 balls) looked like he was batting on a pitch different from the one where the ball was turning from one end to the other, scoring runs without much ado.
With all the confidence in the world, first-innings double centurion Root swept and reverse swept the India spinners, including Ashwin, as runs came at a fast clip when he was in his element in the second session.
He not just negated but also attacked the spinners with aplomb but what Root could not tackle was a delivery that kept low on landing before thudding against the English run-machine's pads.
The umpire had no hesitation in raising his finger as Jasprit Bumrah appealed for an LBW.
Ollie Pope (28), Jos Buttler (24) and Dom Bess (25) made useful contributions, but England strangely kept on batting even after the lead crossed 350 and then 400 on a track which is expected to give the bowlers a lot of purchase on the final day.
While 16 wickets fell on the first three days, a staggering 15 fell by the wayside on Monday and the Chepauk pitch played a major part.
While Ashwin did an admirable job, India captain Virat Kohli may have missed a trick or two by not trying out Washington's off-breaks when left-arm spinner Shahbaz Nadeem was leaking runs, including overstepping on a few occasions and adding to his first innings no balls.
When India came out to bat again, left-arm spinner Jack Leach bowled Rohit with a peach of delivery that landed on the leg-stump before hitting the off-stump, the turn leaving the home team with plenty to worry about going into the final day's play.