DPAPI Primer for Pentesters

Update 6 July 2013 – fixed info when user store may decrypt on separate machine

Understanding DPAPI is not that complicated, although the amount of the documentation can be daunting. There is a lot of excellent “under the hood” DPAPI stuff available (e.g. Stealing Windows Secrets Offline http://www.blackhat.com/html/bh-dc-10/bh-dc-10-briefings.html) But is it easier to steal these secrets online? The answer is yes, probably.

DPAPI’s purpose in life is to store secrets. These are frequently symmetric crypto keys used to encrypt other things. For example, typical use cases for these protected keys are for them to encrypt anything from saved passwords in an RDP connection manager on a Desktop to encrypting sensitive info in a database (e.g. bank account numbers). Using DPAPI to store sensitive info (or store keys that encrypt sensitive info) is good practice.

There are a few concepts to understand before using DPAPI

  • You can encrypt/decrypt the secrets using either a “user store” or a “machine store”. This is where the entropy comes from. What this means is:
    • If you use the user store, then this secret may only be read by this user on this machine. In the testing I’ve done, it cannot be read by the same domain user on a different machine either.
    • If you use the machine store, any user on the machine is able to decrypt the secrets – including Network User (e.g. IIS), Guest, etc. In the testing I’ve done, this is certainly less restrictive/secure than the user store (user store takes into account the machine also).
  • Secondary Entropy: One argument to the DPAPI calls is the secondary entropy argument. Using this, an application needs to know this secret before the data is decrypted.

A few common misconceptions

  • I’ve heard from several people how the user’s login password is used for entropy. This does not really tell the whole story.  An attacker does not need to know the password to retrieve DPAPI, they just need to be executing with the account/machine. This is often an easier problem than retrieving a password.
  • It can be easy to mix up DPAPI and other things that make use of DPAPI. For example, the credential store is an API that uses DPAPI

A pretend good setup

If things are done basically correct, then a good scheme might be something like this:

  • There’s a server database that stores encrypted bank account numbers 
    • It needs to decrypt these for regular use
    • The encryption/integrity of this data uses a good authenticated encryption scheme, say AES/GCM.
  • The question is, where do we store the key?
    • We use DPAPI in user mode to encrypt the data
    • The user used that can access the data is a locked down domain service account with limited permissions. For example, the service account can’t log in to the box, and is a different user than the database runs as.
    • The DPAPI encrypted blob is stored in an ACLed part of the registry so only the service account has access

An overly simplified example might be the following, which runs at deployment time.

using System;
using System.Collections.Generic;
using System.Linq;
using System.Text;
using Microsoft.Win32;
using System.Security.Cryptography;
using System.Security.Principal;
using System.Security.AccessControl;

namespace encrypt_dpapi
    class Program
        private const string MASTER_REG_KEY_PATH = @"SOFTWARE\Contoso\dbapp";
        private const string MASTER_REG_KEY_NAME = @"bankkey";
        private const string SERVICE_ACCT = @"EVIL\_mservice";

        public static void WriteMachineReg(string path, string valuename, string value)
            RegistryKey bank_reg = Registry.LocalMachine.CreateSubKey(MASTER_REG_KEY_PATH);

            //set the ACLs of the key so only service account has access
            RegistrySecurity acl = new RegistrySecurity();
            acl.AddAccessRule(new RegistryAccessRule(SERVICE_ACCT, RegistryRights.FullControl, AccessControlType.Allow));
            acl.SetAccessRuleProtection(true, false);


            //write the key
            bank_reg.SetValue(MASTER_REG_KEY_NAME, value);



        //we want the symmetric key to be randomly generated and no one to even know it!
        public static byte[] genSymmetricKey(int size)
            RNGCryptoServiceProvider rng = new RNGCryptoServiceProvider();
            byte[] buf = new byte[size];
            return buf;

        static void Main(string[] args)
            //check that we're running as the correct service account
            string user = WindowsIdentity.GetCurrent().Name;
            if (!user.Equals(SERVICE_ACCT, StringComparison.OrdinalIgnoreCase))
                Console.WriteLine("Error: must run as " + SERVICE_ACCT + " Account");
                Console.WriteLine("Exiting program");

            //generate a random key we'll use to encrypt bank accounts
            byte[] key = genSymmetricKey(256);
            Console.WriteLine("Key " + Convert.ToBase64String(key));

            byte[] additional_entropy = {0x41, 0x41, 0x41, 0x41};

            //dpapi encrypt the key
            byte[] enc_key = ProtectedData.Protect(key, additional_entropy, DataProtectionScope.CurrentUser);

            //dpapi encrypted key is saved in base64
            WriteMachineReg(MASTER_REG_KEY_PATH, MASTER_REG_KEY_NAME, Convert.ToBase64String(enc_key));


If I run this, I get

Key 721HLUm5n9/0hpAFtBl3Jvn2jJ+KM3z4mPKfyLCHOAZyx/JUP6qs+DCVpwWCqbmB3CZc+o6qXeY4

This is the base64 version of the key used to decrypt bank account numbers – so ultimately what we as attackers want. But if I look in the registry (where this info is stored) I get something completely different



So how can we get decrypted Bank Account Numbers?

Say we’re an attacker and we have system privs on the box above. How can we decrypt the bank account numbers?

There’s probably more than one way. One method may be to scan memory and extract the key from memory (but if it uses safe memory protection it may not be in there long…). Another method may be to attach a debugger to the app and extract it that way. For a production pentest, one of the most straightforward ways just to use DPAPI again to decrypt the data.

using System;
using System.Text;
using System.Runtime.InteropServices;
using System.ComponentModel;
using Microsoft.Win32;
using System.Security.Cryptography;

namespace decrypt_dpapi_reg

    public class registry
        public static string ReadMachineReg(string path, string valuename)
            return (string)Registry.GetValue(path, valuename, "problem");

    class Program

        private const string MASTER_REG_KEY_PATH = @"SOFTWARE\Contoso\dbapp";
        private const string MASTER_REG_KEY_NAME = @"bankkey";
        private const string SERVICE_ACCT = @"EVIL\_mservice";   

        public static byte[] UnprotectUser(string data)
                byte[] additional_entropy = { 0x41, 0x41, 0x41, 0x41 };
                byte[] encryptData = Convert.FromBase64String(data);
                return ProtectedData.Unprotect(encryptData, additional_entropy, DataProtectionScope.CurrentUser);
            catch (CryptographicException e)
                Console.WriteLine("Data was not decrypted. An error occurred.");
                return null;

        static void Main(string[] args)
            //must be run as a user with access on a machine with access
            string s = registry.ReadMachineReg(@"HKEY_LOCAL_MACHINE\" + MASTER_REG_KEY_PATH, MASTER_REG_KEY_NAME);

            Console.WriteLine("DPAPI encrypted key: " + s);

            Console.WriteLine("DPAPI encrypted key: " + BitConverter.ToString(Convert.FromBase64String(s)));

            byte[] decryptedbytes = UnprotectUser(s);


If we try to run this as another user, what happens? It won’t work. We’ll get an exception like this:

System.Security.Cryptography.CryptographicException: Key not valid for use in specified state.

   at System.Security.Cryptography.ProtectedData.Unprotect(Byte[] encryptedData,Byte[] optionalEntropy, DataProtectionScope scope)
   at decrypt_dpapi_reg.Program.UnprotectUser(String data)

DPAPI uses the user entropy to encrypt the data, so we need to compromise the user. But what happens if we copy out the registry value to another machine and try to DPAPI to decrypt the secrets on another box as the EVIL\_mservice account, what happens?

It turns out in my testing this does not work, and I got the same exception as a bad user on the same machine. I needed to run on the same machine that encrypted the key. UPDATE However, there are several reasons it may not work, but it should work overall. From http://support.microsoft.com/kb/309408#6

DPAPI works as expected with roaming profiles for users and computers that are joined to an Active Directory directory service domain. DPAPI data that is stored in the profile acts exactly like any other setting or file that is stored in a roaming profile. Confidential information that the DPAPI helps protect are uploaded to the central profile location during the logoff process and are downloaded from the central profile location when a user logs on.
For DPAPI to work correctly when it uses roaming profiles, the domain user must only be logged on to a single computer in the domain. If the user wants to log on to a different computer that is in the domain, the user must log off the first computer before the user logs on to the second computer. If the user is logged on to multiple computers at the same time, it is likely that DPAPI will not be able to decrypt existing encrypted data correctly.
DPAPI on one computer can decrypt the master key (and the data) on another computer. This functionality is provided by the user’s consistent password that is stored and verified by the domain controller. If an unexpected interruption of the typical process occurs, DPAPI can use the process described in the “Password Reset” section later in this article.
There is a current limitation with roaming profiles between Windows XP-based or Windows Server 2003-based computers and Windows 2000-based computers. If keys are generated or imported on a Windows XP-based or Windows Server 2003-based computer and then stored in a roaming profile, DPAPI cannot decrypt these keys on a Windows 2000-based computer if you are logged on with a roaming user profile. However, a Windows XP-based or Windows Server 2003-based computer can decrypt keys that are generated on a Windows 2000-based computer.

Blackbox Detection

DPAPI can be really tough to do with a complete blackbox. As part of an engagement, if I’ve compromised this far, I usually go hunting for the source which is frequently less protected than the DPAPI protected asset. But one giveaway that you’re even dealing with DPAPI is if a blob has a structure similar to the following:


We can be a bit more scientific about this. Comparing two runs of the same program above gives the following bytes that are the same (note that since the key itself is random but a constant length, this reveals a bit about the structure). This is documented better elsewhere I’m sure, but if something looks quite a bit like this, it should give you a quick idea if you’re dealing with a dpapi encrypted blob.


One Response to DPAPI Primer for Pentesters

  1. Very useful information.

    Once you get privilege escalation DPAPI is pretty much useless. Kernel rootkits can easily be written to monitor calls to DPAPI and log those keys to a file for later viewing.

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