In November 2003, Terry Jones announced she would be retiring from Point of Grace. She was finding it harder and harder to handle a full-time music career and being a full-time wife and mother. She wrote a letter which was posted on the group's website, along with a letter from Heather, Shelley, and Denise. They made it clear that they had no intentions of carrying on as a trio, and called upon band leader Dana Cappillino's wife Leigh to join her husband on tour. Terry's last tour with the group was the 2003 Christmastime Tour with Michael W. Smith, and her last concert was in Little Rock, Arkansas, on February 28, 2004. Leigh had been officially on board since January 1, 2004, but her first concert was in Atlanta, Georgia on March 12, 2004.  Leigh's first album with Point of Grace was I Choose You, released on October 12, 2004. It featured a rawer, less glossy sound. They also worked with producers with whom they had never worked with such as Mark Hammond, Wayne Kirkpatrick and David Zaffiro. Brent Bourgeois, who produced the song "Forever On And On" from the Streams album also produced one track. The album was the most progressive of their career up to that point. They spent the remainder of 2004 doing promotional appearances and participating once again in Michael W. Smith's Christmastime Tour along with The Katinas. In February 2005, they began the I Choose You Tour with Scott Krippayne and special guest Charity Von. The tour took the girls through 30 cities, and the show's set lists featured cuts from I Choose You as well as songs from their back catalog.  After the tour, the girls began work on their second Christmas release. The girls spent the summer of 2005 recording, which, like A Christmas Story, featured holiday classics and original songs. Winter Wonderland was released on October 4, 2005. They launched their first Christmas tour, the Winter Wonderland Tour in late November, playing 16 concerts. The show had John David Webster, who was featured on Winter Wonderland, as a special guests, and local choirs participated in every show.  In 2006, the girls resumed their Girls of Grace activities, and began working with Michael Passons, formerly of Avalon, who began to tour with them. On one-off dates, the girls would have acoustic segments where Dana and Michael would be featured on guitar and piano, respectively, along with vocals from the girls. Heather also gave birth to her third child in 2006. The girls launched the 2006 Winter Wonderland Tour with special guest Scott Krippayne.

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