The true test of the marriage arrived almost immediately after the wedding. In 2006, Ron Isley was convicted on five counts of tax evasion and one count of willful failure to file tax returns, receiving a 37-month prison sentence along with orders to pay $3.1 million in back taxes.
Kandy faced a media circus while pregnant with their first child. In December 2007, she gave birth to Ronald Isley Jr. while Ron was serving his sentence at the Federal Correctional Institution in Terre Haute, Indiana.
During his incarceration, Kandy managed domestic operations, shielded their newborn son from intrusive paparazzi, and visited the facility consistently until Ron's release to a halfway house in April 2010. Longtime industry observers often point to this period as the decisive moment where initial public cynicism shifted toward respect. She proved her commitment under extreme legal and financial strain.