When you work on a brand new unsaved project, if you already have 99 other auto saved items in your auto save folder without clearing out your folder, it will stop auto saving files after Place_Autosave_100.
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This may be intentional to prevent ROBLOX from eating up your disk space with files you never use. While I doubt many people would let it accumulate that many, it may be a good idea to have an error prompt that says “No more space for autosaves. Please delete some of your existing autosaves” when Studio reaches this limit so it doesn’t mysteriously just stop saving.