An inflatable mailer (10, 10') comprising: a. a pouch (12, 12') comprising front and rear sheets (16, 18, 16') that are oriented in face-to-face relation, wherein each sheet (16, 18, 16') comprises: i. a top edge, a bottom edge (24, 24'), and two opposite side edges (20, 22), wherein the sheets (16, 18, 16') are connected along the bottom edge (24, 24') and along opposite side edges (20, 22) to define an interior space, and wherein the top edges of the sheets (16, 18, 16') are unconnected to form an opening (26, 26') into said interior space; and ii. at least one pouch inflation port (19, 21, 19', 21') positioned at the top or bottom edge (24, 24') of at least one sheet (16, 18, 16'); b. an inflatable liner disposed in said interior space, said inflatable liner comprising front and rear webs oriented in face-to-face relation, wherein each web comprises: i. a top edge, a bottom edge (52, 70), and opposite side edges (54, 56), wherein the side edges (54, 56) of the front and rear webs are interconnected and at least one of the top or bottom edges (53, 52, 70) are at least partially connected; ii. two sheets (42, 44) having inner surfaces sealed to each other in a pattern defining a series of inflatable chambers and at least one common channel in fluid communication with said series of inflatable chambers; iii. a liner inflation port (25, 66, 68, 66', 68') disposed in at least one of the two sheets (42, 44) in at least one of the two webs, wherein said liner inflation port (25, 66, 68, 66', 68') is a hole or a slit and wherein said liner inflation ports (25, 66, 68, 66', 68') are aligned with said pouch inflation ports (19, 21, 19', 21'), and whereby an inflation pathway is created through which a portion of gas can be introduced into said liner. a. a pouch (12, 12') comprising front and rear sheets (16, 18, 16') that are oriented in face-to-face relation, wherein each sheet (16, 18, 16') comprises: i. a top edge, a bottom edge (24, 24'), and two opposite side edges (20, 22), wherein the sheets (16, 18, 16') are connected along the bottom edge (24, 24') and along opposite side edges (20, 22) to define an interior space, and wherein the top edges of the sheets (16, 18, 16') are unconnected to form an opening (26, 26') into said interior space; and ii. at least one pouch inflation port (19, 21, 19', 21') positioned at the top or bottom edge (24, 24') of at least one sheet (16, 18, 16'); i. a top edge, a bottom edge (24, 24'), and two opposite side edges (20, 22), wherein the sheets (16, 18, 16') are connected along the bottom edge (24, 24') and along opposite side edges (20, 22) to define an interior space, and wherein the top edges of the sheets (16, 18, 16') are unconnected to form an opening (26, 26') into said interior space; and ii. at least one pouch inflation port (19, 21, 19', 21') positioned at the top or bottom edge (24, 24') of at least one sheet (16, 18, 16'); b. an inflatable liner disposed in said interior space, said inflatable liner comprising front and rear webs oriented in face-to-face relation, wherein each web comprises: i. a top edge, a bottom edge (52, 70), and opposite side edges (54, 56), wherein the side edges (54, 56) of the front and rear webs are interconnected and at least one of the top or bottom edges (53, 52, 70) are at least partially connected; ii. two sheets (42, 44) having inner surfaces sealed to each other in a pattern defining a series of inflatable chambers and at least one common channel in fluid communication with said series of inflatable chambers; iii. a liner inflation port (25, 66, 68, 66', 68') disposed in at least one of the two sheets (42, 44) in at least one of the two webs, wherein said liner inflation port (25, 66, 68, 66', 68') is a hole or a slit and wherein said liner inflation ports (25, 66, 68, 66', 68') are aligned with said pouch inflation ports (19, 21, 19', 21'), and whereby an inflation pathway is created through which a portion of gas can be introduced into said liner. i. a top edge, a bottom edge (52, 70), and opposite side edges (54, 56), wherein the side edges (54, 56) of the front and rear webs are interconnected and at least one of the top or bottom edges (53, 52, 70) are at least partially connected; ii. two sheets (42, 44) having inner surfaces sealed to each other in a pattern defining a series of inflatable chambers and at least one common channel in fluid communication with said series of inflatable chambers; iii. a liner inflation port (25, 66, 68, 66', 68') disposed in at least one of the two sheets (42, 44) in at least one of the two webs, wherein said liner inflation port (25, 66, 68, 66', 68') is a hole or a slit and wherein said liner inflation ports (25, 66, 68, 66', 68') are aligned with said pouch inflation ports (19, 21, 19', 21'), and whereby an inflation pathway is created through which a portion of gas can be introduced into said liner.