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It sadly doesn't make a difference. I have about a dozen keygens on my machine and they get quarantined unless they're zipped behind a password or zipped into a 7z.

Just downloading a zip with a keygens inside, it gets removed from the zip before even unarchiving it.

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Also, AFAIK by spec, the manifest of a zip file is unencrypted, even if the zip "is".

Most scanners are too brain dead to care, but I have come across a few that still quarantine if the manifest lists a file with a blacklisted extension.

Easy solution? Compress to zip, then compress that zip to another zip, with a password.

(Yes, I've spent far too long trying to get work done underneath insane corporate security policies)

Gmail will block you from sending a a password-protected ZIP with anything potentially bad in it, like an EXE, because they can see the individual file headers and central directory, like you say. Unfortunately, if you have a ZIP inside a passworded ZIP it also gets considered dangerous and blocked.

Here's a workaround: rename the .exe file to a .txt file, then put that in a password-protected zip file. Now braindead security scanners have no choice but to believe that it really is a text file.

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