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container Roots growing into ground through container

I have some of my peppers in 5-gallon buckets. Each one has a 4-5 inch hole cut in the bottom for drainage. I've been moving them back an forth between the sidewalk and grass when mowing. I left them on the grass too long and noticed, at least on one, but I suspect all or most, have roots that have grown through the hole into the ground. I want to overwinter some of these. Is there a good chance I will kill them when moving the buckets later? Also is there anything I can do now to reduce or prevent damage when I take them inside?
 
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As long as you don't let them get established enough that when you lift the pot up they rip chunks of the root system 'down' out of the pot, you should be fine.
 
This was from last year and i just ripped it up. The plant was fine and did even better this season. They will be fine!

CAM01886.mp4: http://youtu.be/-jrSH5ziieE
 
JoynersHotPeppers said:
They should be fine, consider it pruning :)
Yup, do it all the time. The process is called "air pruning" and its done to keep your root ball from getting too big. Of course the downside is, it keeps your plants from getting too big also. If you are bringing them inside to overwinter its actually a good thing since you will likely be pruning back some of the branches too.
 
Is the sidewalk your property?  If so why not just put them there and leave them, OR put in walkway stones for the buckets to sit on, or better logistically would be put in walkway stones for people to walk around the peppers on the sidewalk so you can still mow without trimming grass between them or moving them again.
 
Dave2000 said:
Is the sidewalk your property?  If so why not just put them there and leave them, OR put in walkway stones for the buckets to sit on, or better logistically would be put in walkway stones for people to walk around the peppers on the sidewalk so you can still mow without trimming grass between them or moving them again.
Yes, the sidewalk is on our property. It's really just a walkway from our front porch, connecting some steps to another part of the yard. Originally I was leaving them there, and moving to sweep off grass clippings. At some point I got lazy or forgetful and left them on the grass. I'm think I'm going to leave them be until it's time to take any I want to keep, inside. I did notice that they started growing a lot better after roots took hold in the ground. I got my bucket soil mix wrong, or didn't mix it well enough. 
 
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