Over the last decades, the simulation of musical instruments by digital means has become an important part of modern music production and live performance. Since the first release of the Kemper Profiling Amplifier (KPA) in 2011, guitarists have been able to create and store a nearly unlimited number of “digital fingerprints” of amplifier and cabinet setups for live performances and studio productions. However, whether listeners can discriminate between the sounds of the KPA and the original amplifier remains unclear. Thus, we constructed a listening test based on musical examples from both sound sources. In a first approach, the psychoacoustic analysis using mel-frequency cepstrum coefficients (MFCCs) revealed a high degree of timbre similarity between the two sound sources. In a second step, a listening test with N = 177 showed that the overall discrimination performance was d’ = .34, which was a rather small difference (0.0 ≤ d’ ≤ 0.74). A weak relationship between the degree of general musical sophistication and discrimination performance was found. Overall, we suggest that listeners are rarely able to assign audio examples to the correct condition. We conclude that, at least on a perceptual level, our results give no support for a commonly accepted pessimistic attitude toward digital simulations of hardware sounds.