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For shrubs, roses, fruit trees, and ornamental grasses: prune in late winter, around mid-February. What you want to be careful on trees is that you don't prune them so late that you prune out the flowering and fruiting buds.
An important thing to know when you're pruning is the growth habit of your plant. If it's an evergreen, prune in the dormant season before they start putting on new growth. This is an excellent time to shape your shrubs or bring back their height. Give them a heavier pruning now and then maintain it throughout the year.
If they are terribly overgrown, only cut them back a few feet. Let them grow new leaves, then cut them back again. This can be a lengthy process for shrubs that have been neglected for a long time.
Deciduous non-flowering trees and shrubs: you can prune those in the late winter as well.
For things like root-hardy shrubs you want to look for new growth. A good example of this is lantana. When you start to see the new growth come up from the ground, the nice green tissue, then you can prune off everything that's above ground.
Prune spring-flowering trees, shrubs, and roses after they flower to promote new growth and buds for next year.
Pruning stimulates growth. So think about when you want you plant to grow. In late fall as plants are going dormant, you don't want to encourage new growth.