Q. I contacted the Extension Service about my oleander. They sent me a great publication about it but my main concern is pruning. I purchased the dwarf plants two years ago in five gallon containers. They are doing fine but are about four feet high. It is my understanding the plants can be pruned. I need to know the best time to do so and how far down to go without harming them. A. Pruning oleander is very simple, much simpler than many other plants. You can prune them any time of the year but the best time is in the winter. The incorrect way is to use hedge shears if you want flowers consistently. Oleander suckering from base after pruning. You can prune them with hand pruners, preferably a type called a bypass shears. Corona makes good ones that are not very expensive. Count the number of main stems coming from the base of the plant. Identify the oldest (largest in diameter) stems. Remove one third of these larger stems leaving one or two inches above ground. You are done! You will do this about every two or three years. No hedge shears. It takes about ten minutes and no mess to clean up! If there are some unusually long ones remove them from the base as well. Removing larger stems will force new growth like this from the base. Having said this, the absolute best time to do this is February and March but you can do it any time!