The use of automation in digital forensic investigations is not only a technological issue, but also has political and social implications. This work discusses some challenges with the implementation and acceptance of automation in digital forensic investigation, and possible implications for current digital forensic investigators. Current attitudes towards the use of automation in digital forensic investigations are examined, as well as the issue of digital investigators’ knowledge acquisition and retention. The argument is made for a well-planned, careful use of automation going forward that allows for a more efficient and effective use of automation in digital forensic investigations while at the same time attempting to improve the overall quality of expert investigators. Targeting and carefully controlling automated solutions for beginning-investigators may improve the speed and quality of investigations while at the same time letting expert digital investigators spend more time utilizing expert-level knowledge required in manual phases of investigations. By considering how automated solutions are being implemented into digital investigations, investigation unit managers can increase the efficiency of their unit while at the same time maximizing their return on investment for expert-level digital investigator training.