A system and method for enhanced data transfer are disclosed, the method being applicable to a system comprising a computing device configured to transfer data from a portable device. In one embodiment, the computing device stores a fingerprint of the newest record downloaded from a portable device and stops downloading records from the device when a downloaded record matches the fingerprint. In another embodiment, the computing device stores a fingerprint of the newest record downloaded from a portable device and fully processes records that are downloaded from the device after a downloaded record matches the fingerprint. The system may include a portable device configured to adapt its operation responsive to a system fingerprint provided by the computing device. The portable device may be a medical device. The system may be a healthcare data management system.