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Ideally, you should wait to prune until trees have gone dormant in late fall to early winter. The worst times to prune trees are early fall and late summer, as pruning them so close to dormancy makes it difficult for the tree recover before it goes dormant for the season.

Ideally, you’ll have a good enough relationship with your neighbors that you can kindly mention this task in regular conversation. However, every neighbor (and neighborhood) is different. Your best bet will always be to ask directly and nicely, offering to contribute to the tree trimming efforts if you’d like. However, if you are bothered by the tree and your neighbor is unwilling to cut it, you can involve the help of the homeowners’ association or local authorities, if applicable.

Hiring an arborist or tree surgeon is usually more expensive than a standard tree company, but it is often worth the investment. Arborists have education and certifications that standard companies typically lack, leading to a more professional, expert-level service. Their expertise is particularly valuable for diseased or infested trees, as they can ensure safer removal and help prevent the issue from spreading. Additionally, arborists may be necessary for work near power lines, as uncertified companies are often not permitted to service these trees. If your goal is to preserve the health of your trees, an arborist is the best choice. Their services, such as stump grinding, are also performed with greater expertise to ensure a safe depth that won't cause your lawn to collapse over time.

You should avoid cutting off the top of mature cherry trees. This process is called tree topping, and it’s not recommended for cherry trees—or any trees, for that matter. Tree topping removes between one-third to half of the length of the tree trunk, resulting in structurally unsound, fruitless suckers. The only exception is for saplings. Young pie, sour, and tart cherry trees that are over 30 inches tall in the fall or winter before the tree blooms can benefit from heading cuts.