It depends. Some systems, that'll work. In other systems, they look at the actual file content to see if the extension is lying.
this post was submitted on 26 Mar 2026
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It's also worth noting if this is a work system you're evading, some workplaces might take note and may not be too happy.
Should work, yes. A filename is independent of the file contents, and this includes the extension. You can rename it back and forth as much as you like.
Caveats, presuming you'resending via mail:
- There could be a size limitation for attachments
- There could be some sort of content scanning/verification at play
Alternatively, upload the file somewhere and send a link instead
I just tried duplicating and renaming it then renaming it back and it seems to work, locally at least
Yes the file extension isn't part of the file itself. Changing the name isn't destructive.
It's mostly a hint to the operating system of what programs can interact with it, and sometimes to the programs how they should try to interact with it. Depending on the structure of the underlying file, a program may know what to do, or it might freak out, until you give it a reasonable extension.
Renaming the extension back and forth should work fine. If the system you're using just checks filename extensions that should solve your problem. However, it's also likely that such a system would also check the file type (aka MIME type) by scanning the file contents, which just renaming the file would not fool, since it will still recognize it as a zip.