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Boggess starred in The Age of Innocence, as Countess Ellen Olenska at Hartford Stage located in Hartford, Connecticut. The show ran from April 5 – May 6, 2018 before the production moved to Princeton, New Jersey's McCarter Theatre Center for a run from September 7 – October 7, 2018. In her latest appearance, Boggess starred as Danielle de Barbarac in the Alliance Theatre production of Ever After The Musical. Boggess is expected to reprise her role in Ever After for the show's third regional production at the Ordway Center for the Performing Arts in December 2019

In February 2016, she reunited with Ramin Karimloo in the Manhattan Concert Productions' staging of The Secret Garden in which she sang the role of Lily.

On August 8, 2016, Boggess ended her role as Rosalie Mullins in School Of Rock and was replaced by Jennifer Gambatese. After leaving School of Rock, she was set to portray her role as Christine Daaé in Le Fantôme de l'Opéra, the French production of The Phantom of the Opera. However the production has been postponed to further notice due to a fire in the Théâtre Mogador, where the show was supposed to be performed. The Théâtre Mogador was only a few blocks away from the Opéra Garnier, where the actual story of The Phantom of the Opera takes place.

On November 10, 2016, Boggess reunited with her Music in the Air co-star Kristin Chenoweth during her solo show My Love Letter To Broadway.

On December 5, 2016, it was announced that Boggess will embark on her first Australian concert tour in June 2017 making stops in Sydney, Melbourne, and Brisbane. She has recently begun her tour before (January 28, 2017). She is traveling with her cellist sister Summer Boggess.

After completing her role in Phantom of the Opera with Norm Lewis, Boggess returned to her alma mater Millikin University to perform a benefit concert featuring the Class of 2015 BFA Musical Theatre majors. It was based on her Awakening concert at 54 Below, and was held to help raise money for the school's new Theatre & Dance building.

Boggess originated the role of Rebecca Steinberg in the 2015 Broadway production of It Shoulda Been You at the Brooks Atkinson Theatre. The musical—which also starred Boggess' former Master Class co-star Tyne Daly—featured direction by David Hyde Pierce. The show began preview performances on March 17, opened on April 14, and closed on August 9, 2015.

Boggess performed the role of school principal Rosalie Mullins in the Andrew Lloyd Webber musical adaptation of School of Rock at the Winter Garden Theatre. The production began previews on November 9, 2015, and opened on December 6.

In January 2014 Boggess played the role of a lesbian in the short film Russian Broadway Shut Down (protesting the Russian government's response to homosexuality in theater). For several years since 2014, Boggess has identified herself with the often repeated motivational moniker; "You are enough... You are so enough... Its unbelievable how enough you are."

On March 24, 2014, it was announced that Boggess would once again rejoin the Broadway company of The Phantom of the Opera as Christine and reunite with her former Little Mermaid co-star Norm Lewis as the Phantom (who made history as the first African-American actor to play the title role in the Broadway cast). They began their runs on May 12, 2014. Boggess concluded her run as Christine on September 6, 2014 and was replaced by Christine alternate Mary Michael Patterson.

On January 21, 2013, Boggess returned to the role of Christine in The Phantom of the Opera for the Broadway production's 25th anniversary and co-starred opposite Hugh Panaro as The Phantom. She performed the role for a limited six-week engagement till March 2, 2013. She was replaced by Christine alternate Samantha Hill.

Following The Phantom of the Opera Boggess began teaching various musical theater master classes and began to workshop an upcoming musical adaptation of the 1998 film Ever After. However, Boggess was not part of the new musical's world premiere at Papermill Playhouse in 2015. She also made her cabaret debut with a solo show entitled Awakening at New York's 54 Below. The 54 Below shows were recorded for a live debut solo album Awakening: Live at 54 Below, which was released on December 10, 2013 from Broadway Records.

From July 26–28, 2019, Boggess reunited with her Phantom: The Las Vegas Spectacular co-star Anthony Crivello in the Hollywood Bowl's production of Stephen Sondheim's Into the Woods. Boggess starred as "Cinderella" alongside the star studded cast of Sutton Foster (The Baker's Wife), Skylar Astin (The Baker), Patina Miller (The Witch), Gaten Matarazzo (Jack), Shanice Williams (Little Red Riding Hood), Cheyenne Jackson (Cinderella's Prince/The Wolf), and Whoopi Goldberg (The Giant).

Boggess has been involved in a number of extended blog series on the web often in association with Broadway.com. These have included the ten-part series titled Daae Days which includes two episodes where Boggess interviews between 15–20 fellow Broadway actresses who have also portrayed the role of Christine Daae in Phantom of the Opera over the many years of its production. Her second vlog Going Bridal went behind the scenes from rehearsals to opening It Shoulda Been You as Rebecca Steinberg. Boggess has also created a video series with her voice coach Mary Setrakian titled Tea and Spinklers also released in 2014.

Boggess starred in the Off-Broadway show Love, Loss, and What I Wore from February 29, 2012 till the show's closure on March 25, 2012.

In April 2012, Boggess announced that she dropped out of Rebecca and instead joined the cast of the upcoming musical revue Prince of Broadway which pays tribute to director Harold Prince. However, the project was postponed until 2013. On July 2, 2012, Boggess returned to Les Misérables until January 10, 2013. This time she joined the West End company at the Queen's Theatre and took over the role of Fantine.

Boggess once again played the role of Christine Daaé in the 25th anniversary concert of The Phantom of the Opera at the Royal Albert Hall in London with Love Never Dies co-star Ramin Karimloo as the Phantom at the Royal Albert Hall on October 1 and 2, 2011.

From February 2010 to March 2011, Boggess starred as Christine Daaé in the sequel to The Phantom of the Opera, Love Never Dies. She also took part in the Rodgers and Hammerstein Prom at the Royal Albert Hall on August 22, 2010, which was screened on August 28. After leaving Love Never Dies being replaced by Celia Graham, Boggess played Sharon, alongside Tyne Daly, in the Broadway revival of Master Class, beginning on June 14, 2011. The show concluded its limited engagement on September 4, 2011.

While she was performing in The Little Mermaid, Boggess starred opposite Kristin Chenoweth in the Encores! staged concert of Music in the Air in February 2009.

Boggess was then cast in her Broadway debut originating the role of Ariel in The Little Mermaid. She performed with the show in its pre-Broadway tryout at the Denver Center for the Performing Arts' Ellie Caulkins Opera House which ran from July 26, 2007 through September 9, 2007. The Broadway production began previews at the Lunt-Fontanne Theatre on November 3, 2007. The show was then temporarily shut down on November 10, 2007 until November 28, 2007, due to the 2007 Broadway stagehand strike. Performances resumed the next day following the strike and the official opening night was pushed from December 6, 2007 to January 10, 2008. Boggess received positive reviews for her performance. She stayed with the show for a year and a half playing her final performance as Ariel on May 31, 2009. Boggess was replaced by understudy Chelsea Morgan Stock.

Around the time she was performing in Les Misérables, Boggess was cast in the brand new Las Vegas production of Andrew Lloyd Webber'sThe Phantom of the Opera at the Venetian Resort and Casino. The production opened on June 24, 2006. Boggess starred in the female leading role of Christine Daaé co-starring Anthony Crivello and Brent Barrett alternating as The Phantom. She stayed with the Vegas production for a year.

Sierra Boggess was born and raised in Denver, Colorado, with her older sister Summer and her younger sister Allegra. The three of them were members of the Colorado Children's Chorale. Her parents are Kellun Turner Boggess and Michael Boggess. She attended George Washington High School. In an interview with The Interval, Boggess discussed the early influence of drama studies during high school on her early development. She graduated from Millikin University in 2004 with a Bachelor of Fine Arts

Sierra Marjory Boggess (born May 20, 1982) is an American theater actress and singer. She is best known for originating the role of Ariel in The Little Mermaid on Broadway and for her multiple appearances as Christine Daaé in The Phantom of the Opera. Sierra has been involved in several productions of The Phantom of the Opera beginning with the Las Vegas production in 2006. In 2010 she was cast in the role of Christine Daaé in Phantom's sequel Love Never Dies.