A growing body of literature, which looks at probation success among a variety of offenders has done little to investigate the factors associated with probation outcomes for sex offenders. However, a number of static and dynamic factors have been associated with sex offenders’ likelihood of failure after release from prison. An analysis, supported by the U.S. Department of Justice, National Institute of Justice was conducted of 419 adult male sex offenders who entered probation in Maricopa County, AZ between 1997 and 1999. The analysis attempted to examine the success of each probationer for a period of 21 to 51 months after entry to probation. Data were collected on 21 static or historical factors, such as age, race, education, marital status, employment status, and prior alcohol or drug abuse and 16 dynamic factors, such as living alone, positive social supports, current alcohol and other drug problems, motivation to change, and assessed emotions, and analyzed the relationship of each factor to probation failure. Both the likelihood of failure and the time to failure were examined. Select findings include: (1) a technical violation while on probation was found to be significantly associated with 9 of the 21 static factors and 11 of the 16 dynamic factors; (2) arrest for a new offense was associated with 6 static factors and 5 dynamic factors; and (3) probation failure was found with 7 of the static factors and 10 dynamic factors. Factors which were not associated with any of these criminal justice outcomes were: prior treatment for drug or alcohol abuse, prior mental health treatment, entry to probation from prison or jail, life time probation, age of victim, relationship to victim, and force used in the offense. Factors associated with all three outcomes were marital status, employment status, prior use or abuse of drugs, presence of alcohol or drugs at the offense, current problem with alcohol or drugs, motivation to change, and acceptance of responsibility for offense. Study limitations are presented and discussed. Tables and references