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The boreal‐winter stratospheric polar vortex is more disturbed when the quasi‐biennial oscillation (QBO) in the lower stratosphere is in its easterly phase (eQBO), and more stable during the westerly phase (wQBO). This so‐called “Holton–Tan effect” (HTE) is known to involve Rossby waves (RWs) but the details remain obscure. This tropical–extratropical connection is re‐examined in an attempt to explain its intraseasonal variation and its relation to Rossby wave breaking (RWB). Reanalyses in isentropic coordinates from the National Centers for Environmental Prediction Climate Forecast System for the 1979–2017 period are used to evaluate the relevant features of RWB in the context of waveguide, wave–mean‐flow interaction, and the QBO‐induced meridional circulation. During eQBO, the net extratropical wave forcing is enhanced in early winter with ∼25% increase in upward propagating planetary‐scale Rossby waves (PRWs) of zonal wave‐number 1 (wave‐1). RWB is also enhanced in the lower stratosphere, characterized by convergent anomalies in the subtropics and at high latitudes and strengthened waveguide in between at 20°N–40°N, 350–650 K. In late winter, RWB leads to finite amplitude growth, which hinders upward propagating PRWs. The effect is most significant for zonal wave‐numbers 2 and 3 (wave‐2‐3). During wQBO, RWB in association with wave‐2‐3 is enhanced in the upper stratosphere. Wave absorption/mixing in the surf zone reinforces a stable polar vortex in early to middle winter. A poleward confinement of the extratropical waveguide in the upper stratosphere forces RWB to extend downward around January. A strengthening of upward propagating wave‐2‐3 follows and the polar‐vortex response switches from reinforcement to disturbance around February, thus a sign reversal of the HTE in late winter.