Winston Flags Smith has returned with an inspiring new reggae single titled “Try Again,” released on December 12, 2025. The track emphasizes perseverance, delivering a message that aligns with the veteran singer’s roots-inspired style.

Produced by Patrick R. Quest, “Try Again” encourages listeners not to be discouraged by initial setbacks. Through sincere lyrics and a steady reggae groove, Flags reminds audiences that success does not always come on the first or second attempt, and that determination and faith are essential to achieving one’s goals. The song reflects both personal experience and universal truths.

Known for a career that began in Jamaica’s vibrant reggae scene before continuing in the United States, Winston Flags Smith has consistently infused his music with messages of resilience, reflection, and hope. “Try Again” continues this tradition, reinforcing his reputation as an artist who uses music as a source of strength and inspiration.

A few days after the single’s release, the official music video premiered. The video is available for viewing on Maria Jackson 27’s YouTube channel, and the song can be downloaded from all major streaming platforms.