Gmail – How to Trick Gmail with following way of attaching files

gmail

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?

Best Answer

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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