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I have several self seeded oak sprouts under our pine trees. I know they can't stay there at the roots of the large pines. But want to see if the tree sprouts will grow we have 2 1/2 acres & would love more large trees to grow. Can I transplant to better location? When would I do this during the year? I am in Indiana, How do I protect from winter? Do I transplant before winter? Leave them there for winter & transplant in spring? How do I save these tree sprouts in a better location? some only have few leaves at about 6" tall. One has many leaves at about 8" tall. Do I need to keep them there til they are a certain size? Or better to move them as soon as possible?

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Self-seeded (or squirrel-seeded) oaks are pretty tough. Unless you're maximising yield for a commercial operation you can be quite rough with them. I loosen the soil and pull them up rather than digging, so as not to damage the roots of my fruit trees/bushes (but the top few inches of my soil are mostly composted plant matter mixed with light topsoil). Maybe 1 in 10 don't come up cleanly this way if I get them while they're only a few inches high.

Then I chuck them in whatever soil/compost I have lying around (probably last year's potting compost) in whatever pots I have spare, in an out-of-the-way corner of the garden. In pots they do need watering, but can survive drying out for a few days at a time. No saucers so they don't flood. Maybe I lose another 1 in 10 (probably to squirrels) at this stage.

I'd keep them in pots for another couple of years (assuming enough space and enough decent-sized pots). My winters are warmer than yours but I put the pots in the otherwise-empty greenhouse (those squirrels again).

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Dig your little trees up trying to not disturb their roots as much as possible. Transplant into pots with POTTING SOIL. Water when dry, no standing water, very little fertilizer or very dilute, plenty of light and allow them to adjust to the potted temporary homes at least until next spring. In the spring you'll have to "harden" these baby trees before transplanting by allowing them to be in sunlight and weather a few hours and a little more each day. Then transplant them to the location you'd like. Make sure they are not planted with lots of weeds/grasses surrounding them. Plant in holes the depth of their root ball with no amendments! Plant the entire plant and soil from pot in the new hole and hope for the best. Next year, go ahead and add fertilizer. (make sure that the trunk of this little tree is NOT buried or covered by soil, mulch...do not dig that hole any deeper than the depth of the root ball or your tree will sink and the trunk will be compromised by moisture held to the trunk by soil, mulch, rocks whatever). Make a tree well or dammed circle around the initial roots to allow water to sink into the soil below the clay surface soils. Remember that most roots are within 6" of the surface, roots for collecting water and chemicals necessary for your tree. Watering below that is unnecessary unless you are planting a Large Ball and Burlap tree on a slope.

Do not stake!! One thing you could do is to add Mycorrhizae fungal spores. You can purchase in any decent garden store, nursery or better yet a cannabis store. This will vastly help your tree's survival chances.

Meanwhile get a soil test from your closest cooperative extension service...a common service provided by the larger Universities. Watering regularly (do not drown or water until the soils are semi-dry) is critical. You won't be able to plant and forget...The soil tests will tell you what is lacking in the soils that you should replace. MORE IS NOT BETTER AT ALL.

Are there any details we should know about to personalize this further?

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