OutlookToolbox v2 – Now With Less Meh

Hey all,

This post is a revisit to a tool that was introduced in 2017 – OutlookToolbox. When the code was published I was happy with the overall functionality but unhappy with the execution. I wanted to write a C# DLL and forced the implementation. The old version used rundll32 to access C# functions which were exported with using Robert Giesecke’s Unmanaged Exports. The final result was a DLL and Aggressor script that wrote the DLL to disk and received status updates via txt files; so janky. Well enter Cobalt Strike’s new feature – in-memory .NET assembly execution. Long story short, we can run OutlookToolbox in-memory with only the odd csv or msg file ever touching the disk.

Code – https://github.com/ThunderGunExpress/OutlookToolbox_v2

What It Is

A C# console application that interfaces with Outlook in the background.

How to Defend

Sophisticated threat-actors are using this tactic. They are harvesting our emails for information that allows them to get closer to their objectives. The good news it that we can control how external background access to Outlook is handled – see Microsoft’s link here. If I recall correctly, if Outlook is set to Always warn me about suspicious activity the tool will stop during the SanityCheck (anti-popup) function. OutlookToolbox will do just fine with the other two configurations, the check AV one is the default.


  • SanityCheck – Checks Outlook’s popup configuration (via registry and wmi) and attempts to determine if interfacing with Outlook will cause a popup.
  • EnumerateFolders – Lists all the folders within Outlook (inbox, sent items, conversation history, and so on).
  • FolderToCSV – Exports all the contents of a folder to CSV which includes – From, To, Type (it can get at Lync messages),  . The message’s body is truncated to 1000 characters.
  • ExportMessage – Exports target email or collection of emails from a specific sender.
  • EnumerateTarget – Check the GAL for target user’s details like manager, colleagues (reports to same manager), title, and alias. Could be used in conjunction with EmailPivot.
  • EmailPivot – Sends a crafted email on behalf of the target session. Great for getting in that trust chain (or whatever it’s called) between two people. Also has the ability to send replies from the TO user directly to deleted items with Outlook rules. Don’t do this unless you absolutely know what you are doing. Clean up could be difficult and it’s incredibly nasty.


Check out the old OutlookToolbox post for screenshots. There are some minor changes but the UI is pretty much the same.

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