Card readers with adaptive magnetic head assemblies are disclosed. According to one embodiment, a card reader may include chassis comprising a card slot that receives a portion of a magnetic stripe card; a card guiding element positioned in a card path defined by the card slot and that interacts with a datum edge of the magnetic stripe card, at least a portion of the card guiding element being rotatable relative to the card path; and a magnetic reading head provided on the card guiding element that reads a magnetic stripe on the magnetic stripe card. The card guiding element and the magnetic reading head rotate relative to the card path in response to the datum edge of the magnetic stripe card applying a force to the card guiding element, thereby substantially maintaining an alignment between the magnetic stripe and the magnetic reading head.