Track-assisted mass is a proxy for jet mass that only uses direction information from charged particles, allowing it to be measured at the Large Hadron Collider with very fine angular resolution. In this paper, we introduce a generalization of track-assisted mass and analyze its performance in both parton shower generators and resummed calculations. For the original track-assisted mass, the track-only mass is rescaled by the charged energy fraction of the jet. In our generalization, the rescaling factor includes both per-jet and ensemble-averaged information, facilitating a closer correspondence to ordinary jet mass. Using the track function formalism in electron-positron collisions, we calculate the spectrum of generalized track-assisted mass to next-to-leading-logarithmic order with leading-order matching. These resummed calculations provide theoretical insight into the close correspondence between track-assisted mass and ordinary jet mass. With the growing importance of jet grooming algorithms, we also calculate track-assisted mass on soft-drop groomed jets.