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August to September is ideal for most areas. This will allow the tree to get settled in the soil before frosty temperatures hit. Wait until the seedling is about 18 inches tall though. Because frost damage is a huge concern for these plants, wait until spring if your area experiences temperatures below 30°F (-1.1°C). Choose a location that receives lots of direct sunlight to encourage an additional growth spurt. The hole will only need to be a few inches deep. A good rule of thumb is to make it a little deeper than the container the tree was initially grown in.  You can use a small shovel or your hand to dig the hole. The good thing about olive trees is that they can tolerate most soil types. This includes rocky or sandy soil. The only requirement is that it must have good drainage or they will slowly decline and die due to too much moisture. Poorly-drained soil conditions can lead to root disease such as Verticillium wilt or Phytopthora root rot. The area around the tree should never be muddy, just slightly moist. Gently remove the tree, being cautious not to disturb the roots too much. Ensure the tree and the hole are well watered before planting. Place the tree in the hole, slightly higher than the ground and cover with one inch of soil from the area.  Avoid using large amounts of organic soil mix, compost or fertilizer. This will create an artificial growing environment. You can start fertilizing the tree a year after planting  If you are planting multiple trees, they need to be at least three feet apart, and up to 28 feet (8.5 m) for larger varieties. Otherwise, they will compete for nutrients in the surrounding soil. The same rules apply when watering the trees outdoors. Check the area around the tree for moisture and water when the top ¼ inch is dry. Be sure not to over water.  Mother nature will take over and the plant will flourish. Olive trees are quite tough, so they do not normally require any special care or watering during the colder months. However, if the climate in your area is very dry, water them as normal to maintain moisture in the upper levels of the soil. Remember that with hundreds of varieties, it's difficult to predict when the tree will begin producing fruit. Some, like Arbequina and Koroneiki will bear fruit around 3 years old. Others may take 5-12 years. Olives grow very slowly, so don't require much pruning. However, you can remove dead, diseased or dying branches, and remove branches growing low on the trunk. You can also thin out branches to allow light to reach the center of the tree.
Plant in the fall. Dig a hole. Plant the tree. Water as normal. Expect fruit in 3 years. Prune the tree.