Electrical tree propagation is a precursor to dielectric failure in high voltage polymeric insulation. Tree growth has been widely studied under AC conditions, but its behavior under DC is not well understood. The aim of this work was to examine the importance of polarity and initiating defect size on DC tree propagation. Electrical tree propagation in epoxy resin under constant DC voltages of +60 kV and −60 kV was measured in samples with classical needle-plane electrodes, but with small initial trees (< 100 μm) incepted under lower AC voltages before the DC tests. Experimental results showed strong polarity dependence. In either polarity, the length of the initial AC tree had a major influence on the inception of the subsequent DC tree. The effect was attributed to the defect being influential if it is larger than the space charge injection region. As a consequence, there is a critical defect size that will accelerate failure of DC insulation dependent on space charge injection behavior of the polymer/electrode system in question — a critical finding for high voltage asset management.