Gmail – Send .exe Files Without Special Actions by the Recipient

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I read through this: How can I send a Windows executable via Gmail? (and similar questions here and on SO), but all of the answers I came across rely on the email recipient doing something special such as

  • changing filename extensions, or
  • accessing cloud storage services.

First, linking to another cloud service is not sending via Gmail. There are reasons you may not want to use an outside service.

Second…What about sending e-mails to people who are not tech-savvy?

There are many kinds of files that Google does not want attached directly (described here https://support.google.com/mail/answer/6590?hl=en), but you should still be able to send them in some way that

  • leaves them accessible to casual computer users (who may have file extensions hidden, for example), and
  • does not require the use of other cloud services.

Best Answer

Create a self-extracting archive with 7-Zip, make sure it is password protected and the file names are encrypted:

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Google will not detect the exe inside and let it through. The recipient has just to know the password (don’t send that with Gmail :)).