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When I try to grow "upside-down" tomatoes, they always curve back up towards the sun and eventually break, causing massive damage. Could I be doing something wrong, or is there a way to avoid this?

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You could prevent this by supporting them using a spiral growing stick. I have the same problem and this is what I'm going to try next year. Also: mastergardeners.org/picks/tomato_staking.html –  Peter Jun 8 '11 at 19:31
    
well i just tried the upside down planter for the first time and have run into this problem so im gonna try a flood light on the ground they put off some heat and light my planter is about 6 feet off the grounded a lamp pointed the direction of the plant butbfar enough a way not to burn it –  user2277 May 21 '13 at 13:11
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up vote 16 down vote accepted

There was just an article on upside-down planting in the June 2011 edition of Consumer Reports on this topic. They tested out topsy-turvy tomato planters to see how tomatos grown in these containers compare to traditionally planted tomatoes. Their answer to your question:

Tomato shoots are geotropic: They try to turn up in response to gravity. But Topsy Turvy plants slump as they grow, often twisting their stems, which can cause splitting.

It may be interesting to experiment with growing indeterminate vs. determinate tomato plants in your upside-down planter. Determinate plants are bushy and more rigid, indeterminate are viney. I would think the flexible/bendable nature of indeterminate tomatoes may make them less likely to break in an up-side-down planter.

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Tomatoes are very phototropic: the stalks will always grow towards light, so instead of pointing downwards, they try to curve upwards. Also, the stalks themselves aren't very strong, so as they grow, the weight of new growth pulls the stalks over, causing the twisting and breaking.

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