On the September 3, 2018, episode of "Raw", Michaels made a special appearance to promote the match between Triple H and The Undertaker at Super Show-Down, during which he was confronted by The Undertaker himself. At Super Show-Down, Michaels assisted Triple H in defeating The Undertaker, after which, he was attacked by Undertaker and Kane. On the October 8 edition of "Raw", Michaels appeared with Triple H and announced that he was coming out of retirement to reform D-Generation X. On the October 29 edition of "Raw", Michaels delivered Sweet Chin Music to the Undertaker. At Crown Jewel, D-Generation X defeated The Brothers of Destruction. The match was poorly received by fans and critics alike, winning the Wrestling Observer Newsletter's "Worst Match of the Year" award. Afterwards, Michaels confirmed that he would be going back into retirement. On November 27, 2018, it was announced that Michaels was officially working as a writer and producer on WWE's NXT brand and show. On the February 25, 2019 episode of WWE Raw, Michaels along with special guests Ricky Steamboat, Kurt Angle and Sting appeared during the main event segment to celebrate the 70th birthday of Ric Flair. However, Flair would be attacked by Batista instead of appearing on-screen. In April 2019, Michaels was inducted into the WWE Hall of Fame for the second time as a member of D-Generation X as part of the 2019 class.