Morgan's next album Greater Need was released in 1996. Leading off the singles was the Jon Randall duet "By My Side", which became Randall's only top 40 hit. The song was originally intended to be a duet with Kershaw, but after his label expressed disinterest, the then-president of Morgan's label suggested that she cut it with Randall. While the followup single "I Just Might Be" failed to make top 40 on Hot Country Songs, the album's last single "Good as I Was to You" reached number four in 1997. Morgan said that she wanted the album to show her "maturing musically" over her previous works. She noted that she had originally declined the album's title track until she was encouraged by Thom Schuyler, a singer-songwriter who was also the president of artists and repertoire (A&R) at her label at the time, at which point she realized the song was indicative of the musical themes she wanted to pursue on the album. The album included guest vocals from Vince Gill, Travis Tritt, and her son Jesse Keith Whitley. James Stroud produced the album, and contributing musicians included Dann Huff, Paul Franklin, Billy Joe Walker Jr., Glenn Worf, Alison Krauss, and former Toto member David Hungate. Thom Owens of AllMusic, Alanna Nash of Entertainment Weekly, and Jeffrey B. Remz of Country Standard Time all praised the album for its varied sounds, with particular emphasis on its ballads.
Morgan married country singer Jon Randall in 1996, and a year later, she published an autobiography, Forever Yours, Faithfully: My Love Story. In 1998, tabloids published allegations that Morgan had been spotted in the back of a limousine with Bill Clinton, then the President of the United States, but Morgan dismissed the claims as "fabricated". Morgan and Randall divorced in 1999. She married her fifth husband, singer Sammy Kershaw, on September 29, 2001. Morgan filed for divorce, citing irreconcilable differences on October 23, 2007. In 2008, Morgan filed for Chapter 7 bankruptcy, with an estimated $1 to $10 million in debts. She would later state that her bankruptcy was because she "didn't watch [her] own money" or audit her accountants. Her sixth marriage took place on September 15, 2010, to Tennessee businessman Randy White.