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overwintering Overwintering Questions

I will be needing to pull my plants inside here soon and need a question answered before I get to cutting....
 
My plants are currently in large square storage totes (18gal) because I had them and was too cheap to buy 5gal buckets.
 
The roots have 'fanned' out in the totes since they had so much room, will it hurt the plants to cut back the roots to place them into 5gal pots? (since my local grow shop has some nice pots with bottom trays for a decent price)
 
My totes just have holes drilled into the bottom and sides to allow water to drain out onto the ground when watered since they were outside but that will not work for inside. 
 
Check out the overwintering guide stickied to the top of this forum. Good pictures. It's a long read, but a good one. I'll be drastically chopping my plants down to 10" sticks and cutting the roots back just as hard. Probably putting them into 1 or 2 gallon pots for winter. I don't have space for bushes during the winter. I also don't have good lights to support a lot of foliage, so I'm hoping the hard reset will keep things manageable. Best of luck. My frosts are coming in a few weeks still...I hope
 
The Comprehensive Guide to Over-Wintering
 
only126db said:
I will be needing to pull my plants inside here soon and need a question answered before I get to cutting....
 
My plants are currently in large square storage totes (18gal) because I had them and was too cheap to buy 5gal buckets.
 
The roots have 'fanned' out in the totes since they had so much room, will it hurt the plants to cut back the roots to place them into 5gal pots? (since my local grow shop has some nice pots with bottom trays for a decent price)
 
My totes just have holes drilled into the bottom and sides to allow water to drain out onto the ground when watered since they were outside but that will not work for inside. 
I haven't had any issues with pruning the roots. I think it helps the plant too. To help prevent an aphidapocalypse, you might want to spray the roots and stems/leaves really really well after cutting back, maybe even dip in a mild soap solution, then rinse and repot in a clean container with fresh mix. If you put in 5 gal buckets, you'll need drain holes in those as well. I would do them like your totes, holes along the sides, up to about 3 inches from the bottom, and on the bottom of the bucket.When you water it periodically, take it outside, or over a sink, somewhere it can drain. Then you can set it in a tray or something to catch any excess after. The holes allow proper drainage after watering, but also expose the soil to more oxygen which will help the roots. 
 
In my experience, pepper plants are pretty forgiving and will survive drastic surgery to both branches and roots prior to overwintering. As Malarky said, you can cut them back and fit them into a 1-gallon pot. The plants will probably begin budding out new growth fairly quickly and then stay that way through the winter. Peter's aphid advice is spot on: don't let them infest the new growth. The plants shouldn't need much water since there is very little top growth.
 
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