We investigate the boundedness of the H ∞ -calculus by estimating the bound b(ε) of the mapping H ∞ → B(X): f → f (A)T (ε) for ε near zero. Here, −A generates the analytic semigroup T and H ∞ is the space of bounded analytic functions on a domain strictly containing the spectrum of A. We show that b(ε) = O(| log ε|) in general, whereas b(ε) = O(1) for bounded calculi. This generalizes a result by Vitse and complements work by Haase and Rozendaal for non-analytic semigroups. We discuss the sharpness of our bounds and show that single square function estimates yield b(ε) = O( | log ε|).