Webs of inflatable mailer pouches and associated methods are disclosed. Pouches include a multilayer inner cushion structure with inflatable compartments and a fill channel disposed at a first longitudinal edge of the structure. An outer layer with a closure flap is secured to the inner structure. The inner cushion structure and outer layer are folded at a bottom edge of the pouch to form first and second panels of the pouches. The fill channel may be disposed at a top of the first panel and the closure flap disposed at a top of either the first or the second panel. The fill channel extends beyond a top of the second panel and the closure flap is extendable beyond the top of the fill channel. When wound, the closure flap is folded so that the fill channel of each pouch layer is exposed at a lateral face of the cylinder.