In a sad, mournful, or sorrowful manner; expressing deep grief or melancholy.
From dole (Old English dāl meaning portion or grief) + -ful + -ly. The word evolved from meaning 'a portion' to 'sorrow or grief' by the 13th century, and -fully adds the adverbial sense of 'in a doleful manner.'
The word 'dole' shares the same root as 'doll' (a small portion) and 'deal,' which is why we still say 'unemployment dole' in British English—it's literally a portion handed out to those in need, making 'dolefully' sound like mourning for lost opportunity.
Complete word intelligence in one call. Free tier — 50 lookups/day.