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Sending Emails from Image for Windows V2 to Servers that Require SSL

Note: Image for Windows V3 includes native support for sending emails to servers that use SSL and TLS.


Image for Windows (IFW) V2 does not natively support sending emails to a server that requires SSL. Doing so results in an error when IFW attempts to send the email.


Sending emails from Image for Windows to servers that require SSL (such as can be accomplished by using the stunnel program.


  1. Download stunnel from Select an appropriate download site and then select the installer (e.g. stunnel-4.53-installer.exe).

  2. Run the installer to install stunnel on the system. The default installation path is in the C:\Program Files or C:\Program Files (x86) folder. Depending on your version of Windows, you many want to install to a non-system folder to provide easier access to the program and its files (e.g. C:\stunnel). Select the desired components to install (for normal email sending with IFW it's not necessary to install the Self-signed Certificate Tools component). Creating the program shortcuts is recommended to allow easy access to the program.

  3. Before running stunnel it's necessary to edit its configuration file. Note that if you installed to the default location you may need administrator privileges to edit and save the file. Use Explorer (or the Command Prompt) and navigate to the installation folder. Edit the stunnel.conf file (e.g. from the Command Prompt, run notepad stunnel.conf). Make the following changes to the file:

    • Note: To comment out a line, place a semi-colon at the start of the line.
    • Comment out the following line (located about 22 lines down): cert = stunnel.pem
    • Scroll down a little further to the Service definitions section and comment out the entire [pop3s], [imaps], and [ssmtp] sections (each section has three lines to comment out).
    • Scroll down a little further and uncomment the [gmail-smtp] section (remove the semi-colon from the beginning of all four lines).
    • Still in the [gmail-smtp] section, change the incoming port number to the one you want to use when sending from IFW. In this example, port 259 will be used. The entire [gmail-smtp] section will then be as follows:
      [gmail-smtp]client = yes
      accept =
      connect =
    • Save the changes to the file and exit Notepad.

  4. Run stunnel. This can be done using the Desktop shortcut or from the Programs menu. The program will be accessible from its tray icon.

  5. Configure the IFW command line to send the email using the port specified in the stunnel.conf file. For example (the following should all be on one line):
    "\Program Files (x86)\TeraByte Unlimited\Image for Windows\V2\imagew.exe" /b /uy /d:w0@0x1 /f:"e:\Backups\Windows7"
    /email:localhost***"Subject: IFW Operation (~ec~)"*259**password

    "" would be the gmail account's address (e.g.
    "password" would be the gmail account's password (or the cached password, if using that feature of IFW).

    This example shows using a cached password, MyEmailPassword (the following should all be on one line):
    "\Program Files (x86)\TeraByte Unlimited\Image for Windows\V2\imagew.exe" /b /uy /d:w0@0x1 /f:"e:\Backups\Windows7"
    /email:localhost***"Subject: IFW Operation (~ec~)"*259**{#MyEmailPassword#}

  6. Run the IFW operation and test that the email is sent properly.


Technical Notes:

  • Email settings can be configured in the IFW.INI file if not wanted on the command line. This stops the email log in information from being displayed in the email's text. Alternatively, the email password can be cached by IFW.

  • If desired, stunnel can be configured to run as a service (these options are available in stunnel's Start Menu shortcuts).

  • Documentation for stunnel can be found here:

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