When the game makes a new autosave, it should
a) check if there is a free "autosave slot" and use it
b) if no autosave slots are free, overwrite the oldest autosave
The first autosave after starting OpenTTD will always be called "autosave0", followed by "autosave1" and so on. When exiting and restarting OpenTTD, the next autosave will again be called "autosave0" because the counter resets.
In some cases, this might end up actually overwriting the newest autosave first, which is highly unintuitive and unexpected.
Steps to reproduce
Start the executable, start a new game, fast-forward until it has created a couple of autosaves. Exit & restart the executable, start a new game, fast-forward until a new autosave is created. Check file creation dates in the autosave folder.
Note that the "keep_all_autosave" settings has to be "false", which it is by default.
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