Prune oleanders in early spring, before they flower on new wood. They can tolerate very severe pruning if heavily damaged during winter, but in general a lighter, more selective thinning will preserve shrub size and form. Severe pruning encourages too much vegetative growth and fewer flowers.
Remove dead wood and any damaged or diseased stems. Remove suckers and water sprouts that shoot up from oleander roots and lower sections of stems. Too many suckers--especially on young plants--will use up plant energy that would otherwise produce flowers.
Promote flowering by trimming the ends of stems, which will encourage branching and more blooms. Stimulate continued blooming throughout the summer by trimming spent flower clusters and stem tips.
Rejuvenate an overgrown shrub over several years. Remove one-third of thick older stems the first year, cutting them back to within 12 inches of the ground. Remove one-half of the mature stems remaining the second year. Also head back new shoots to stimulate branching. Repeat both steps during the final year.
Watch dwarf oleander cultivars, usually grown as ground covers, for occasional tall shoots. Immediately remove these. Also remove shoots that die back during the growing season, which sometimes happens with dwarf and miniature varieties.