Dryocosmus kuriphilus Yasumatsu, an invasive gall wasp originating from Asia, is the latest serious pest attacking Castanea sativa Mill. in Europe; the negative effects on fruit and wood production are considerable. The most effective defense strategy is biological control, but parasitoid effectiveness requires at least 6–10 years to reduce damage to acceptable levels. In Italy, prolonged productivity losses could adversely affect human activity in chestnut orchard stands, resulting in negative socio-economic and hydrogeologic consequences. Thus, it is necessary to quickly reduce the impacts of the infestation to avoid degradation of chestnut stands during the time delay required for parasitoid efficiency. We examined green pruning as a means to reduce negative impacts of gall wasps and stimulate healthy shoots in a young chestnut coppice in Central Italy. Two different pruning cuts (Long- and Short-cut) on growing shoots and four timings of application were tested. The development and phytosanitary status of nodes was observed over 2 years on pruned and control sprouts. Pruning was effective in reducing gall wasp damage though responses varied among pruning techniques and application times. Long-cut pruning made in spring during the full growth phase induced a higher number of new and better-developed shoots. Pruning during the end of the egg-laying period of the gall wasps promoted development of only healthy new shoots. Our results indicate that is possible, by choosing the best combination of time and technique, to identify a pruning method useful to maintain growth and development of C. sativa stands threatened by D. kuriphilus.