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cryptsetupwill format and use files, it does not really help you at all in creating or managing them. So it's all up to you how you do it. There are many different ways to change a file's size; I usually do it withtruncate --sizebut if you get the size wrong the data is gone... the example shown in Windigo's answer should be safer. And then you still have to resize whatever is encrypted inside the image.