Drilling the bottom out of a terracotta pot?

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Has anyone done this?
I've got two Box ball shrubs in small square terracotta pots. They are looking stressed compared to the dwarf hedge around not to mention a nightmare to water. I can't get larger square terracotta pots and putting them in the ground they will disappear as a decorative feature
I'm thinking if I drill out the base the roots can go into the soil while retaining the look.
I've watched and read and you should soak it first and not use the hammer function. But I'm nervous of what I would do with the plants if the pots break. Can't find anything square to take their place.
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The only normal people you know are the ones you don’t know very well
The only normal people you know are the ones you don’t know very well
I'm no glue guru and whenever I need to glue anything, I tend to try whatever comes to hand first during a quick rummage through the garage! That would mean it would be PVA or superglue for most tasks and I reckon either would work on terracotta pots, with superglue possibly providing a neater finish.
The only normal people you know are the ones you don’t know very well
You can get inserts for pots which allow water to drain into the base, as the lack of drainage holes could mean the pot is waterlogged rather than too dry.
https://www.bloomling.uk/elho/milano-easy-insert-30-cm
The only normal people you know are the ones you don’t know very well