A medicament delivery device (100) for delivery of medicament from a container (12) into an injection site through a cannula (16). The device comprises a chassis (106), a drive mechanism (400) for driving a piston member (22) along a container axis (A) to expel the medicament through the cannula (16), and a carriage (200) for retaining the container (12), the cannula (16) and the drive mechanism (400). An insertion mechanism (70, 120, 130, 504) is provided for moving the carriage (200) in an insertion direction (H) relative to the chassis (106), and a cannula bending mechanism (300) is provided for bending the cannula (16) about a bending axis (B) to substantially align at least an end part of the cannula (16) with the insertion direction (H) prior to movement of the carriage (200) in the insertion direction (H).