"Someday (I Will Understand)" is a song recorded by American singer Britney Spears. It was written by Spears and produced by Guy Sigsworth. The song was released on August 18, 2005, by Jive Records, as the sole single from Spears' first extended play, Britney & Kevin: Chaotic (2005). In July 2004, Spears announced her engagement to American dancer Kevin Federline, later revealing she would be taking another career break to start a family. Spears wrote the song two weeks before knowing she was pregnant with her first child, Sean Preston Federline. A pop ballad, "Someday (I Will Understand)" lyrics refer to a feeling of empowerment as a pregnant woman. A remixed version of the song was included on the 2005 remix compilation, B in the Mix: The Remixes.

"Someday (I Will Understand)" has received mixed reviews from music critics. A few reviewers considered it as a lesson on the singer's history and a "tear-jerker" ballad, while others considered it a non-savable "flop single". The song reached the top ten in Denmark, Sweden and Switzerland and also charted in a number of European countries. An accompanying music video, directed by Michael Haussman, premiered on the finale of Britney & Kevin: Chaotic. Entirely shot in black-and-white, the music video features Spears as a pregnant woman and portrays a transformation of her character.

In July 2004, Spears announced her engagement to American dancer Kevin Federline, whom she had met three months before. The romance received intense attention from the media, since Federline had recently broken up with actress Shar Jackson, who was still pregnant with their second child at the time. The initial stages of their relationship were chronicled in Spears's first reality show Britney & Kevin: Chaotic. They held a wedding ceremony on September 18, 2004, but were not legally married until three weeks later on October 6 due to a delay finalizing the couple's prenuptial agreement. In October 2004, the singer announced she would be taking another career break to start a family. Spears gave birth to her first child, Sean Preston Federline, on September 14, 2005.

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