We characterize the UMD property of a Banach space by tail inequalities for maximal functions of tangent conditionally symmetric processes. More precisely, we prove that a Banach space $V$ is UMD if and only if for some (equivalently, for all) $p\in(0,\infty)$ one has that \[ \mathbb P(\sup_{r\geq 0} \| N_r\|>t)\lesssim_{p,V}\Bigl(\frac{s^p}{t^p}+\mathbb P(\sup_{r\geq 0} \| M_r\|>s)\Bigr), \qquad s,t>0, \] for all tangent conditionally symmetric $V$-valued processes $M$ and $N$. We further show that this estimate is equivalent to suitable Lorentz norm inequalities for the associated maximal functions, and obtain analogous characterizations in the discrete-time, continuous-time, and purely discontinuous settings.