Abstract: Medical port protection adapters are described herein. In one aspect, a contamination guard can include a proximal collar adapted and configured to engage with a medical port; an elastomeric medial region coupled to the proximal collar; and a distal collar coupled to the proximal collar by the elastomeric medial region; where the elastomeric medial region is adapted and configured to: bias the distal collar to extend at least partially over a distal end of the port when in an unloaded position; and allow the distal collar to resiliently travel proximally when loaded to permit engagement with the distal end of the medical port.