The seeming absolute promise of forgiveness in 1 John 1:9 is not so absolute when placed into the context of John’s epistle and Jesus’ teaching on forgiveness. This paper examines the context of this promise and statements in the epistle that indicate there are caveats to experiencing the forgiveness promised. Jesus’ warning after the disciples’ prayer in Matthew 6 and warning about the consequences of failing to forgive will demonstrate those caveats. The first section will discuss the nature of conditional and unconditional promises and how they impact the promise of 1 John. Next, the statements in 1 John that indicate the presence of caveats will be identified and evaluated. The third section will examine Jesus’ warnings in Matthew 6 and 18 and relate them to the issues raised in John’s epistle. Following this will be an examination of the relationship between conditional (sanctification) forgiveness and absolute judicial (justification) forgiveness. I will argue that failure to forgive and experience forgiveness will not result in a loss of salvation but will impact one’s experience in this life and at the judgment seat of Christ. If these truths are understood and properly applied, the maturing believer will be motivated to practice aggressive forgiveness, always with an eye on pleasing the One who forgave them first.