Low molecular weight, highly crosslinked silicone resins are widely used as reinforcing agents for highly transparent elastomers and adhesion/tack promoters in gels. The resins are complex mixtures and their structure / property relationships are ill defined. We report the synthesis of a library of 2, 3 and 4-fold hyperbranched polymeric oils that are comprised of linear, lightly branched or highly branched dendronic structures. Rheological examination of the fluids and tack measurements of gels filled with 10, 25 or 50% dendronic oils were made. Viscosity of the hyperbranched oils themselves was related to molecular weight, but more significantly to branch density. The properties are driven by chain entanglement. When cured into a silicone gel, less densely branched materials were more effective in improving tack than either linear oils or Me3SiO-rich, very highly branched oils of comparable molecular weight, because the latter oils underwent phase separation.