Ubuntu – Rewriting git history: interactive rebase has problems with file renaming & deleting

We use git to store our PC board designs. We are a small company and the only person doing commits & pushes is the board designer (me), so there’s no risk of overwriting someone else’s work by rewriting git history.

We recently had to change our OS from Linux (Ubuntu) to Windows. Several files in our repos violate Windows filename rules (e.g. contain a colon, path too long, etc.). I sometimes need to check out previous commits to see the design history, so ideally the entire history needs to contain valid Windows filenames, otherwise the checkout fails.

Doing an interactive git rebase seemed like it could solve the problem. Unfortunately git doesn’t handle things the way I was hoping.

For example, I have a file called file:1.txt that was renamed file:2.txt several commits later. Because this file wasn’t critical, I decided to delete it using a git interactive rebase. I deleted it it from the first commit where it appeared. I thought git would know that it had been deleted & update the subsequent commits accordingly. Unfortunately that’s not what happened. Rebase got to the subsequent commit where the file was renamed, and gave a conflict because it was trying to change the name of a file that no longer existed.

A few other similar issues popped up in my attempts with other files/paths, but the basic problem seemed to be that a git interactive rebase doesn’t always handle filename changes or file deletions well. It doesn’t seem to make all the necessary adjustments to the git history automatically.

Am I missing something here? Is there a better way to do this?

BTW, for context I would say that I’m an intermediate git user. I’ve used basic commands for awhile, but I’ve rarely used the advanced ones (e.g. rebasing), and I know nothing of the plumbing commands – nor do I write external scripts to accomplish git tasks.

Thanks!