We initiate the study of outer automorphism groups of special groups $G$, in the Haglund–Wise sense. We show that $\operatorname {Out}(G)$ is infinite if and only if $G$ splits over a co-abelian subgroup of a centraliser and there exists an infinite-order ‘generalised Dehn twist’. Similarly, the coarse-median preserving subgroup $\operatorname {Out}_{\rm cmp}(G)$ is infinite if and only if $G$ splits over an actual centraliser and there exists an infinite-order coarse-median-preserving generalised Dehn twist. The proof is based on constructing and analysing non-small, stable $G$-actions on $\mathbb {R}$-trees whose arc-stabilisers are centralisers or closely related subgroups. Interestingly, tripod-stabilisers can be arbitrary centralisers, and thus are large subgroups of $G$. As a result of independent interest, we determine when generalised Dehn twists associated to splittings of $G$ preserve the coarse median structure.

Let $C$ be a curve in a closed orientable surface $F$ of genus $g\geq 2$ that separates $F$ into subsurfaces $\widetilde {{F}_{i} } $ of genera ${g}_{i} $, for $i= 1, 2$. We study the set of roots in $\mathrm{Mod} (F)$ of the Dehn twist ${t}_{C} $ about $C$. All roots arise from pairs of ${C}_{{n}_{i} } $-actions on the $\widetilde {{F}_{i} } $, where $n= \mathrm{lcm} ({n}_{1} , {n}_{2} )$ is the degree of the root, that satisfy a certain compatibility condition. The ${C}_{{n}_{i} } $-actions are of a kind that we call nestled actions, and we classify them using tuples that we call data sets. The compatibility condition can be expressed by a simple formula, allowing a classification of all roots of ${t}_{C} $ by compatible pairs of data sets. We use these data set pairs to classify all roots for $g= 2$ and $g= 3$. We show that there is always a root of degree at least $2{g}^{2} + 2g$, while $n\leq 4{g}^{2} + 2g$. We also give some additional applications.