How to Send Executable .exe Files in Gmail?

Gmail is one of the popular email services available free for users. In addition to easy integration with other Google services, the popularity comes with its robust security features. However, sometime this security can prevent you from sending some file types in emails as an attachment. Sending executable files with .exe extension in Gmail is one such a problem and in this article, we will explain how you can do that.

Sending Executable .exe Files

It might be there is a program file (executable) you want to send to a friend that one can’t download through the internet. Gmail blocks executable (.exe) files as they serve as means of transmitting a virus to the mail receiver. You will see a message like below indicating “Blocked for security reasons!” and Gmail will not allow you to send the email.

Ways to Send Executable (.exe) Files in Gmail

There are two ways you can send executable .exe files in Gmail. You can use one of these options depending upon your situation.

1. Use Google Drive to Send Executable Files in Gmail

Google Drive is a service Google provide and can be used in the Gmail interface to send an attachment. You only have to log on to your Gmail account and compose the mail you want to send.

Then, click the double triangle icon with the title “Insert files using Drive” when you hover on it. Your Google drive dashboard appears for you to insert the file.

Tap the “Upload” menu at the top and click the “select files from your device”, locate, select and hit the “Open” button to choose the executable file you want to send from your computer.

Click the “Upload” button after the file has appeared in the dashboard. Allow for the uploading to be complete, and you will now have it as an attachment in your composed mail dashboard.

Now, you can hit the “Send” button, and something like “Someone needs access to the (executable file name)” comes up and has the email of the receiver with the “Share with people“.

Just leave everything as it is if it appears like this, and finally click the “Send” button. Thus, your message would be sent without hindrance and be received successfully. Note that there isn’t any demand on the email receiver must use Gmail, as anyone using any email provider can receive, view and download the executable file you send.

2. Change .exe Extension to Send Executable File in Gmail

Gmail detects a file that is executable through its extension (.exe), flags it and prevents any message with such attachment from sending. To overcome this, you can change the .exe to another file extension that works with Gmail. In our example, we will show how to change extension to .txt and to the receiver.

The normal renaming from .exe to .txt won’t work as Gmail would still flag it but encoding the file type while being renamed to .txt works pretty well. This method is so technical (both for the user and receiver) because it requires understanding how to use the Command Prompt in Windows. In our examples, we will use the following stuffs:

• Original file – npp.8.4.1.Installer.x64.exe
• Renamed file – npp.8.4.1.Installer.x64.txt
• File location – Downloads folder

So, search for the “Command Prompt” app, open it and follow suit with these commands. Since our file is in our “Downloads” folder, we are to change the directory by entering “cd Downloads” in the prompt and clicking the enter key. Make sure to change the directory (cd) in prompt to the correct location where you have the .exe file on your computer.

Then, another command is certutil -encode infile outfile, and our infile here is “npp.8.4.1.Installer.x64.exe”, while the outfile should be “npp.8.4.1.Installer.x64.txt” as we are encoding and changing the file name as the same time.

After the successful completion, you can find the file you encoded and changed as we have shown ours thus. Now head over to compose a mail. 

Click the spiral icon with the title “Attach files”, select the file on your computer and click the “Open” button to have it as an attachment in your mail. Remember to leave a message on how your receiver would be able to decode and run the executable file, as we have shown in our illustration here. The receiver can simply use the infile as .txt file and outfile as .exe in the above command.

Finally, click the “send” button, and the message would deliver successfully without hassle.

Wrap Up

The most common method to achieve this has always been to upload the executable file to any online drive or free file hosting site and insert the link in the email message. Notwithstanding, in using the above method, the first is for non-technical people while the second is for technical people. Meanwhile, remember Gmail doesn’t allow you to send more than 25MB as attachments through email.