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I often develop apps in Visual Studio that contains some invalid file types for Gmail to be attached (e.g. Form's EXE file), in the past I easily Zipped or RARed my folder with some arbitrary extension e.g. FileName.abc or FileName.123 this way Gmail never blocked my attachment.

But since a few months they have updated, most probably they check the file contents to decide what kind of file it actually is, so I am stumped, I cant use my good old trick to attach such files. I have to upload on Drive or Dropbox But I don't like this method, it is lengthy especially considering email is already opened, and often the attachment sizes are less than 20 MB

Is there any way?

UPDATE:

I tried with all the above methods, still, nothing works, Gmail somehow decides its a security risk. And they are just normal EXE files (they do not involve any security level or system level access, just a desktop application to read data from local excel file)

I did try following methods as by default they involve more steps than uploading on Drive or Dropbox

  • Splitting the file and then attaching

  • Dragging my zip file inside a word document, then attaching Word document in email (this method actually works when combined with other methods e.g. Password protect or extensionless file name) but still it's very lengthy

Any other possibility please?

migrated from superuser.com Aug 25 '18 at 20:05

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  • Password protected the compressed files, then they can't look in them. – Tetsujin Aug 25 '18 at 9:52
  • @Tetsujin It wouldn't work since archive files are banned by google too. They offer to upload such files on google drive instead. – Alex Aug 25 '18 at 12:33
  • Another I have tried which also DOES NOT work: change valid DOCX or XLSX file extension to ZIP, explore, put exe in any of the folders, return from zip to DOCX/XLSX. Does not work!!! – leoinlios Dec 25 '18 at 15:34
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Methods for transferring touchy files on Gmail :

  1. Compress/zip with a password. This may involve compressing twice, because even with a password Gmail can still see the names of the contained files. So to be safe compress once without password, then compress again the archive with a password.
  2. Send via Google Drive using the "Insert files using Drive" button and upload the file (see article).
  3. A bit farfetched : Append the archive to a small image. Some archive managers like WINRAR can still open the mangled archive (see article).
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You can try to remove the extension of the attached file to trick it. Additionally PW it or zip it. Another option would be to split it in parts (either with 7zip or HJSplit - http://www.hjsplit.org/).

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