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How to send .exe files as attachments (blocked attachments) in Outlook?

Normally when sending an email with EXE attachments in Outlook, the attached EXE files will be blocked in recipients’ Outlook as below screenshot shown. So how could you send emails with EXE attachments, but prevent recipients’ Outlook from blocking the EXE attachments? There are two solutions:

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For example, others sent an EXE installation package to you via Outlook email. However, the EXE attachment is recognized as potentially unsafe file and blocked as below screenshot shown. Here, I'd like to recommend Kutools for Outlook's Safe Attachment Extensions option for you, which can help you quickly unblock unsafe attachments with several clicks only. Click for 60-day free trial without limitation!
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arrow blue right bubble Send .exe files as attachments with renaming them firstly

This method will guide you to rename the extension name of the EXE file before attaching it in your email. Please do as follows:

1. In Windows 10/8, open the folder containing the EXE file you will attach in the File Explorer, and then click View > File name extensions to show all file extensions. See screenshot:

Note: If you are working in Windows 7, please show the file extensions as follows: (1) you can click Organize > Folder and Search Options to open the Folder Options dialog box; (2) uncheck the Hide extensions for known file types option on the View tab, and click the OK button. See screenshot:

2. Double click to select the EXE file’s file name, and then change its extension name from exe to e_x_e, and press the Enter key. See screenshot:

3. In the popping out Rename box, please click the Yes button.

4. Click Home > New Email to create a new email in Outlook, and then click Insert > Attach File > Browse This PC (or Insert > Attach File). See screenshot:

5. Now in the Insert File dialog box, (1) please open the folder containing the EXE file whose extension name you changed just now, (2) select the EXE file, (3) and click the Insert button. See screenshot:

6. Now the EXE file with changed extension name is added as attachment in the email, please compose the email and send it.

Note: After your recipients receiving this email, they can save the EXE file to their computer firstly, and then change the extension name from e_x_e to exe.


arrow blue right bubble Send .exe files as attachments with Kutools for Outlook

If you have Kutools for Outlook installed, its Auto compress all outing attachments option will compress all attachments to zipped files automatically, so does the EXE attachments.

1. Click Kutools > Options. See screenshot below:

doc send exe files 01

2. In the opening Attachments Options dialog box, please check the Auto compress attachments before sending emails option on the Compress tab, and click the Ok button. See screenshot above:
doc send exe files 02

3. Click Home > New Email to create a new email, and then click Insert > Attach File > Browse This PC (or Insert > Attach File). See screenshot:

4. In the opening Insert File dialog box, (1) open the folder containing the EXE file you will attach, (2) select the EXE file, (3) and click the Insert button. See screenshot below:

doc send exe files 7

5. Compose the email and send it. And then a warning Microsoft Outlook dialog box comes out, please click the Yes button to go ahead.

And now the attached EXE file is compressed to zipped file automatically in the outgoing email. Your recipients will get the zipped EXE file in the email, and he/she can use EXE file normally after uncompressing the attachment.

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Demo: Send .exe files as attachments (blocked attachments) in Outlook

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arrow blue right bubbleRelated Articles


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  • Auto CC/BCC by rules when sending email; Auto Forward Multiple Emails by custom; Auto Reply without exchange server, and more automatic features...
  • BCC Warning - show message when you try to reply all if your mail address is in the BCC list; Remind When Missing Attachments, and more remind features...
  • Reply (All) With All Attachments in the mail conversation; Reply Many Emails in seconds; Auto Add Greeting when reply; Add Date into subject...
  • Attachment Tools: Manage All Attachments in All Mails, Auto Detach, Compress All, Rename All, Save All... Quick Report, Count Selected Mails...
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