Background

I was recently helping a friend to track down a scammer that stole money from them. I wanted to get the scammer's IP address that could be provided to the police, and I thought that sending them an email with embedded tracking image would be the easiest way to get it. I was surprised to find out that there is no native support for embedding remote images in Outlook - every attempt resulted in the image being included in the email itself. That would not work for our purpose, obviously, as we needed the scammer's email client to download the picture from our server, which would in turn log their IP address to a log file. This guide and a collection of scripts will allow you to setup a similar targetted tracking operation. This is not a rocket science, and you won't get any more information about your target than any and every newsletter collects about you. Still, I encourage you to use this for tracking bad people only.

Requirements

1. Server with a LAMP stack for hosting the image. (I use DigitalOcean for my server needs. They are great.)
2. Microsoft Outlook for sending the email

Server setup

1. Prepare the image you want to embed in the tracking email, and update rows 2 and 4 in image.php to contain the correct filename
2. Upload your image file, image.php, and index.php to /var/www/html/ folder on your server
3. Visit http://your-servers-ip-address/image.php?img=contract_termination.png in your browser and verify that an entry was created in http://your-servers-ip-address/log.txt

Embedding the remote image in Outlook for Mac

1. Create a new email message, and put xxx in place where you want to put your tracking image
2. Go File > Save As Template…
3. Open the .emltpl file in a text editor and search for xxx. The file will have two copies of your text. The first one is a plaintext version of the email (used e.g. on Apple Watch), the second one is an HTML version that we want to edit to contain our image.
4. Replace xxx with <img src="http://your-servers-ip-address/image.php?img=contract_termination.png"> and save the file
5. Open the .emltpl file in Outlook and send the email

Embedding the remote image in Outlook for Windows

1. Create a new email message, and put xxx in place where you want to put your tracking image
2. Go File > Save As > Outlook Template (*.oft)
3. Press Alt + F11 to open the Visual Basic interface
4. Go Insert > Module
5. Paste the content of vb.txt (don't forget to change the path to your oft file on row 3)
6. Run the script by pressing the green play icon
7. You'll get a dialog window with an input box. Paste the following code into the box and press OK: <img src="http://your-servers-ip-address/image.php?img=contract_termination.png">
8. You'll get a new window containing your email with the tracking image embedded. Just send it.