Abstract: An inflatable packaging assembly (10) comprising a container (12) and a flexible bag (28). The container (12) has a base (14) and a number of upstanding walls (16) extending from the base (14) to a container opening (18) for receiving and storing a package item (20). One of the upstanding walls (16) includes an aperture (26) passing through the wall (16). The bag (28) includes first (30) and second (32) bag panels having peripheral edges (34) sealed together to define an inflatable chamber. A bag opening (36) extends through a portion of the sealed edges (34) for receiving a fluid medium to inflate the bag (28). A filling valve (38) extends through the bag opening (36) and into the inflatable chamber. The filling valve (38) includes a flexible sealing port (40) and a filling tube (46). The filling tube (46) has a first end (48) secured to the sealing port (40) and a semi-rigid second end (50) extending out from the bag opening (36).