Cable management systems, devices, and associated methods of installation and operation are disclosed herein. In one embodiment, an enclosure for holding computer components includes a front panel, a back panel, and a side panel between the front panel and the back panel. The side panel has a first side facing an interior space of the enclosure and a second side facing away from the first side. The enclosure also includes a guide panel proximate to the side panel, the guide panel being spaced apart from the second side of the side panel by a gap extending at least partially between the front panel and the back panel. The enclosure also includes a cable anchor located in the gap between the side panel and the guide panel.