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For quite awhile if you wanted to send a .exe attachment in Gmail you could rename the extension and it would go right on through. However, within the last couple of weeks these attachments are now being blocked. And it seems like it's only being blocked on some Gmail addresses, or from certain senders.

For example, I can send an email from [email protected] to my own Gmail address with an exe attachment renamed to .exx, and it will go on through.

But an email from [email protected] with the exact same attachment to the same Gmail address will be blocked.

I can send the attachment to my address OK, but sending to a different Gmail address gets blocked.

Any ideas?

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    Because the email was bounced back with the standard Gmail "mx.google.com gave this error: This message was blocked because its content presents a potential security issue." message. XYZCorp.com is a representation of my work domain. I can send the mail from my work address and it goes through, a coworker can send the same mail and it gets blocked by gmail server.
    – RobertT
    Commented Dec 23, 2014 at 17:12

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Google used to release upgrades frequently and also it will be applied in account after user confirmation. I believe that it is the reason for one can upload and one can not. Please try zipping after renaming the executable file and try sending it.

Note : make sure that you have hidden the extension in file

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  • These emails are not being sent from a GMail address, so there are no user accounts to confirm. I've tried renaming the file, zipping it, and then renaming the ZIP file before attaching but it still blocks it. These are not password protected ZIPs either.
    – RobertT
    Commented Dec 24, 2014 at 13:37

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