by the NFL on a conditional basis, allowing him to report to training camp and participate in meetings, but is not permitted to participate in games or practices until the conditions are met. He was fully reinstated by the league the following week. On August 30, he visited with the NFL's chief medical director in what was reported to be a proactive meeting to discuss his treatment and progress. In early September, a report surfaced in the media that Gregory may have suffered a substance abuse relapse during the month of August. Although he was called to the New York League Headquarters for a private meeting, no further discipline was applied. On February 26, 2019, Gregory was suspended indefinitely by the NFL for violating the league's substance abuse policy and the terms of his conditional reinstatement. On April 2, 2019, the Cowboys extended Gregory's contract through the 2020 season. In March 2020, ESPN reported that Gregory filed for reinstatement with the NFL. On September 7, 2020, Gregory was conditionally reinstated from suspension, and the Cowboys were given a roster exemption for him through the first six games of the season. On September 8, he signed a one-year extension. He was activated from the roster exemption on October 20, 2020. In Week 7 he made his season debut against the Washington Football Team. In Week 12 on Thanksgiving, he recorded his first career multi-sack game, with two sacks on Alex Smith during the 41–16 loss against the Washington Football Team. He appeared in 10 games, registering 17 tackles (3 for loss), 3.5 sacks (tied for third on the team), 16 quarterback hurries (third on the team), one pass breakup and three forced fumbles (third on the team). In Week 16 against Philadelphia Eagles, he had 3 tackles (one for loss), 1.5 sacks, 2 quarterback hurries, 3 forced fumbles and one pass breakup. He emerged in the second half of the season and began taking playing time at right defensive end from starter Aldon Smith. He finished with 17 tackles (3 for loss), 3.5 sacks, 16 quarterback pressures, one pass breakup and 3 forced fumbles. Gregory entered the 2021 season as a starting defensive end for the Cowboys. He suffered a calf injury during practice before Week 10 and was placed on injured reserve on November 11, 2021. He was activated on December 11. On December 12, 2021 against the Washington Football