A stent delivery system comprising: a stent locatable in a sinus ostium when in an insertion state and conformable from the insertion state to a deployment state when located in the sinus ostium; and an insertion device (100; 110; 120) configured to deliver the stent into the sinus ostium, the device (100; 110; 120) comprising: a handle (104; 114; 124) including an actuation mechanism; a shaft (106; 116; 126) having a proximal end and a distal end, wherein the shaft (106; 116; 126) proximal end is coupled to the handle (104; 114; 124); a wire (105; 115; 125) extending through the shaft having a proximal end and a distal end, wherein the wire proximal end is operatively connected to the actuation mechanism; a first holding member (108; 118; 128) coupled to the shaft distal end; a second holding member coupled (109; 119; 129) to the wire distal end; and a longitudinally compressible and radially expandable elastomeric member coupled to the first holding member (108; 118; 128) at a first end and to the second holding member (109; 119; 129) at a second end, the elastomeric member having a radial thickness forming a through-bore in a longitudinal direction sized to slidingly receive the wire (105; 115; 125) and is selectively compressible longitudinally between the first end and the second end to expand a diameter of the elastomeric member, wherein the stent is positionable around the elastomeric member, wherein actuation of the actuation mechanism in a first direction translates the second holding member (109; 119; 129) toward to the first holding member (108; 118; 128) to compress the elastomeric member, which in turn acts to expand the diameter of the elastomeric member such that, when the stent is positioned around the elastomeric member, the stent expands to the deployment state, and wherein actuation of the actuation mechanism in a second direction translates the second holding member (109; 119; 129) away from the first holding member (108; 118; 128) to uncompress the elastomeric member, which in turn acts to contract the diameter of the elastomeric member such that, when the stent is positioned around the elastomeric member, the stent in the deployment state is released from the insertion device; and when in the deployment state, the elastomeric member is configured to expand to impart an hourglass conformation to the shape of the stent. a stent locatable in a sinus ostium when in an insertion state and conformable from the insertion state to a deployment state when located in the sinus ostium; and an insertion device (100; 110; 120) configured to deliver the stent into the sinus ostium, the device (100; 110; 120) comprising: a handle (104; 114; 124) including an actuation mechanism; a shaft (106; 116; 126) having a proximal end and a distal end, wherein the shaft (106; 116; 126) proximal end is coupled to the handle (104; 114; 124); a wire (105; 115; 125) extending through the shaft having a proximal end and a distal end, wherein the wire proximal end is operatively connected to the actuation mechanism; a first holding member (108; 118; 128) coupled to the shaft distal end; a second holding member coupled (109; 119; 129) to the wire distal end; and a handle (104; 114; 124) including an actuation mechanism; a shaft (106; 116; 126) having a proximal end and a distal end, wherein the shaft (106; 116; 126) proximal end is coupled to the handle (104; 114; 124); a wire (105; 115; 125) extending through the shaft having a proximal end and a distal end, wherein the wire proximal end is operatively connected to the actuation mechanism; a first holding member (108; 118; 128) coupled to the shaft distal end; a second holding member coupled (109; 119; 129) to the wire distal end; and a longitudinally compressible and radially expandable elastomeric member coupled to the first holding member (108; 118; 128) at a first end and to the second holding member (109; 119; 129) at a second end, the elastomeric member having a radial thickness forming a through-bore in a longitudinal direction sized to slidingly receive the wire (105; 115; 125) and is selectively compressible longitudinally between the first end and the second end to expand a diameter of the elastomeric member, wherein the stent is positionable around the elastomeric member, wherein actuation of the actuation mechanism in a first direction translates the second holding member (109; 119; 129) toward to the first holding member (108; 118; 128) to compress the elastomeric member, which in turn acts to expand the diameter of the elastomeric member such that, when the stent is positioned around the elastomeric member, the stent expands to the deployment state, and wherein actuation of the actuation mechanism in a second direction translates the second holding member (109; 119; 129) away from the first holding member (108; 118; 128) to uncompress the elastomeric member, which in turn acts to contract the diameter of the elastomeric member such that, when the stent is positioned around the elastomeric member, the stent in the deployment state is released from the insertion device; and when in the deployment state, the elastomeric member is configured to expand to impart an hourglass conformation to the shape of the stent.