Answer: If you're sure your ivy needs repotting, either through evidence of escaping roots from the drainage holes of the pot, or because it's been in its present pot for 3-4 years, you can repot rather painlessly. Lay the plant on its side and gently work the old pot away. While it's still on it's side, massage the roots to loosen some of the old potting soil. You don't need to remove all the old soil, just enough so you can check the root system to make sure it isn't growing around and around in the shape of the pot, and just enough so the roots are not one solid mass.
Choose a pot one size larger than the old pot and place some moistened potting soil in the bottom. Stand the ivy, support stake and all, in the new pot and work potting soil in and around the roots. When you've filled the pot to the top, water well to help settle the soil. Your ivy should come through the repotting process without skipping a beat.
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