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Convert Debian Jessie to Ubuntu Server 16.04 (without doing a clean install from bootable media)

Convert Debian Jessie to Ubuntu Server 16.04 (without doing a clean install from bootable media)

I would like to convert my debian jessie machine into an ubuntu server machine. Ideally, I just want to swap out all the core packages, preserving my users, files, and other settings. Is this even possible, or am I...