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You should perform gutter cleaning twice a year for maximum effectiveness. If you encounter a blockage when gutter cleaning, insert a hose or pressure washer at the bottom of the gutter and form a seal to keep the water from draining out. You can build pressure on the blockage in this manner to help clear it away. Unless the blockage is an object such as a rubber ball lodged in gutter which needs to be manually removed, the blockage should clear out because of the water pressure. You can then resume gutter cleaning as normal.