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I have never seen this before in large pots

We had a bad storm roll by and it knocked all my plants over. When I went out to pick them up I noticed this. This was the case with most of my plants.
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You would need a REALLY large container to not get roots out the bottom... Given the opportunity, they might even fill a child's inflatable swimming pool.
 
If you had grown your plants on dirt instead of the concrete driveway the roots would have grown out the bottom and anchored the pot to the ground and won't tip over as easily.
 
If you had grown your plants on dirt instead of the concrete driveway the roots would have grown out the bottom and anchored the pot to the ground and won't tip over as easily.

I see Chililover is located in Canada, while I'm merely in northern Ohio. The weather here will likely start killing off chile plants left outside in the next two months or so - I'm sure Chililover will get too cold even sooner. I've got my chile's on the cement as well, to ensure I can easily move them inside when the time is right. While letting them anchor to the ground is good for reducing tip-overs, I think it will also reduce the ability to move them inside for the winter. So the question seems to be whether Chililover wants to bring them inside for the winter or not, or if cutting the root at the drainage holes will cause any issues when bringing them in for the winter.
 
If you had grown your plants on dirt instead of the concrete driveway the roots would have grown out the bottom and anchored the pot to the ground and won't tip over as easily.



That's how it works with my potted peppers. I've got one in a 15 gallon pot that grew through the bottom,
 
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