Not sure if this is the right question but, I recently reinstalled Ubuntu and had some files that I didn't back up. Is it possible to boot from the vmlinuz.old to recover these files and if so, how would I do so?
2 Answers
No. It is possible to boot from an old kernel*, but that will not help you recover files. You should ask another question about how to recover the files.

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The short answer is no.
Booting vmlinuz.old will simply boot from the previous kernel rather than the current kernel. It does not restore files that you overwrote by formatting or repartitioning a disk during a re-installation of the operating system.
Barring the use of data recovery methods outside the scope of this website, you can effectively consider the data permanently lost.
If the data you are seeking to recover is on a disk that you did not repartition or format, you can easily recover it, assuming you know where it is. A standard reinstallation procedure would normally involve formatting your drive. If you did not explicitly omit formatting your disk, your data is likely gone for all practical purposes.

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"Barring the use of data recovery methods outside the scope of this website, you can effectively consider the data permanently lost." I wouldn't be so fatalist about it. At least, there are some recovery tools like
testdisk
that may be able to recover the lost data. – wjandrea Mar 02 '18 at 00:14
vmlinuz
means the kernel; vm=virtual memory; z=compressed in *nix or posix kernel speak. It'll just use an old kernel, and all files will be the same, so I can't see how it can help you? What are you after? – guiverc Mar 02 '18 at 00:01