An inflatable web is disclosed. The web includes first and second film plies sealed together via a plurality of generally transverse seals to define a first and second inflatable chambers and an inflation region. The chambers are inflatable with a fluid and operable to contain the fluid. The sealed plies have a first longitudinal edge and a second longitudinal edge. The web defines a separation region extending at least partially transversely across the web between the first and second inflatable chambers and is configured to facilitate separation thereof. The separation region includes a tear propagation line extending transversely across at least a portion of the web with an end of the tear propagation line terminating proximal to the first longitudinal edge of the web. The separation region includes a tear initiation feature including edges spaced apart from one another longitudinally to form a permanent opening in the web.