I would like to update every single file's commit message within GitHub at certain times.
Whenever I make a major upgrade (merging development into stable branch), I would like to commit and push my changes to GitHub such that all of the files, even those which have had no changes, have the same commit message.
Example:
I could go through every file and add a newline to the end of the file, but I feel as though there may be a way to do this from git or github itself.
If you want to track a point in time for things like released, use a tag instead. Don't "hack" the commit process like you suggest. How would you then find the real diff between checks?
That's simply not how git works, adding nonsense to the history of all files is likely to be very counter productive whenever you need to review it.
You might find gitflow to be a useful read. You don't have to use it - but the explanation of workflow may help you understand how better to use git.
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