Congress has directed the United States Sentencing Commission to ensure that the Federal sentencing guidelines make allowances for sentences other than imprisonment for certain first-time offenders. The desire to give a break to first-time offenders often springs from the same human desire to allow people the opportunity to be rehabilitated and the wish to have them rejoin society. It is preferable to reintegrate first-time offenders into the community than to incarcerate the individuals because of the cost and the stigma. Using data from the Sentencing Commission’s Intensive Study Sample as well as the 1999 Sourcebook of Federal Sentencing Statistics, an intensive study was conducted of 1,918 individual Federal cases. This data showed that a substantial number of offenders who had no prior convictions were lumped together with offenders who might be recidivists or who might have prior violent felonies. While the general impulse was to treat such offenders differently, it was important to differentiate between true first-time offenders and those who might have prior convictions that, under current practice, might be excluded from the criminal history score. Consideration should be given to including present excludable prior convictions that contain any elements of dangerousness or that might be predictive of future criminality. Modifications to the criminal history categories are proposed, along with recommendations that the establishment of a guided downward departure for true first-time offenders is done. Or, in the alternative, it is recommended that a new criminal history category be created for those same offenders. 18 tables and 171 notes.