In 1599 he was sent back to Ireland with Essex during the Nine Years War; during Essex's disastrous attempts to pacify Ireland, Docwra was occupied with attempting to subdue the O'Byrne clan in County Wicklow.
In 1599 he was sent back to Ireland with Essex during the Nine Years War, acting as his chief adviser on Irish military affairs. During Essex's disastrous attempts to pacify Ireland, Docwra was occupied with attempting to subdue the O'Byrne clan in County Wicklow.