Plantar pressure measurement is an important tool in gait analysis. Manual placement of small masks (masking) is increasingly used to calculate plantar pressure characteristics. Little is known concerning the reliability of manual masking. The aim of this study was to determine the reliability of masking on 2D plantar pressure footprints, in a population with forefoot deformity (i.e. hallux valgus). Using a random repeated-measure design, four observers identified the third metatarsal head on a peak-pressure barefoot footprint, using a small mask. Subsequently, the location of all five metatarsal heads was identified, using the same size of masks and the same protocol. The 2D positional variation of the masks and the peak pressure (PP) and pressure time integral (PTI) values of each mask were calculated. For single-masking the lowest inter-observer reliability was found for the distal-proximal direction, causing a clear, adverse impact on the reliability of the pressure characteristics (PP and PTI). In the medial-lateral direction the inter-observer reliability could be scored as high. Intra-observer reliability was better and could be scored as high or good for both directions, with a correlated improved reliability of the pressure characteristics. Reliability of multi-masking showed a similar pattern, but overall values tended to be lower. Therefore, small sized masking in order to define pressure characteristics in the forefoot should be done with care.