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I have cherry tomatoes seedlings that have started to pop up. when should I put them in my upside down home-made planter? Does the stalk have to be a certain thickness? Is there any info on when we should transplant seedlings to upside down planters?

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Just plant it when the root mass is big enough so that it won't fall out of the hole ie. can support itself, and not so big that you can't fit it through the hole. So, clearly the size of the plant depends on how big a hole you've made in your upside planter.

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