A web-guiding system for guiding a web of media travelling from upstream to downstream along a transport path in an in-track direction, including a web-guiding structure and an air source. The web-guiding structure includes an exterior surface having a pattern of recesses formed into the exterior surface, wherein the web of media travels past the web-guiding structure with a first side of the web of media contacting at least some non-recessed portions of the exterior surface of the web-guiding structure. The air source provides an air flow between the first side of the web of media and the exterior surface of the web-guiding structure thereby providing a lifting force to lift portions of the web of media overlying the recesses away from the exterior surface of the web-guiding structure.