Before we delve into the intricacies of individual methods of anti-debugging let’s use this post to define the classes of anti-debugging that we will be discussing. While other classes may exist, the definition of these classes is an attempt to include the majority of anti-debugging methods in use today. There is some overlap between classifications and we may have left out some methods due to limited exposure or effectiveness.

API Based Anti-Debugging
API based anti-debugging is the most straightforward and possibly the easiest to understand for a typical developer. Using both documented and undocumented API calls, these methods query process and system information to determine the existence or operation of a debugger. From single line calls such as IsDebuggerPresent() and CheckRemoteDebugger() to slightly more complex methods including debugger detaching and CloseHandle() checks. These methods are generally trivial to add to an existing code base and many can even be implemented in as few as two or three lines.

Exception Based Anti-Debugging
Exception based anti-debugging is slightly different than your basic API based techniques. Many times when a debugger is attached to a process, exceptions are trapped and handled by the debugger without regard to passing the exception back to the application for continued execution. Occasionally these exceptions can even crash or terminate a process when run under a debugger and be handled gracefully when running clean. It is these discrepancies that makes exception based anti-debugging techniques possible.

Process and Thread Block Anti-Debugging
Some of the API based anti-debugging methods use published functions to query information from within the process and thread blocks for our running code. Many API based detections can be subverted within a debugger by hooking the API call and returning values that indicate a clean process. One way around this subversion is to directly query the process and thread blocks, bypassing the API calls. Direct analysis of the process and thread blocks, while more complex, can lead to a more accurate and high assurance result.

Modified Code Anti-Debugging
One of the methods that a debugger uses to signal a breakpoint is to insert a break byte into the running code at the location that it wishes to stop execution. The process execution breaks when this value is seen, giving control to the debugger. When the program is resumed, the breakpoint value is removed and replaced with the original byte, the execution backed up one byte, and the program is resumed. Detection of software based breakpoints can be achieved by analyzing the process for modifications from the expected norm.

Hardware and Register Based Anti-Debugging
A second way that a debugger can break the execution of a process is by using a hardware breakpoint. A hardware breakpoint relies upon CPU registers to store the pertinent information and to detect when the target break addresses are seen on the bus. A break interrupt is triggered at the appropriate time based on these register values. Reading or modifying the hardware can allow for the detection of a debugger.

Timing and Latency Anti-Debugging
Finally timing and latency can be used as an effective anti-debugging method. When executing a program within a debugger, specifically when single stepping, a much larger latency occurs between execution of instructions. This latency can be detected and compared against a reasonable threshold to detect the existence of a debugger attached to our process.

Each of the classes of anti-debugging outlined above has merit when used individually to protect a process. While none of them can be assured to ever protect a program from a determined reverse engineer or debugger, implementation of these techniques (or many of them if appropriate) can sufficiently slow down the debugging process and hopefully make the attacker spend his time on other, easier, ventures. In the remainder of this series on anti-debugging we will review in depth some of the more interesting methods of each of the above classes. So bring along your debugger and your development environment and let the games begin.

Hash functions are the most commonly used cryptographic primitive, and the most poorly understood. You can think of them as fingerprint functions: They take an arbitrary long data stream and return a fixed length, and effectively unique, string. The security comes from the fact that while it's easy to generate the fingerprint from a file, it's infeasible to go the other way and generate a file given a fingerprint.

Originally created to make digital signatures more efficient, hashes are now used to secure the very fundamentals of our information infrastructure: in password logins, secure web connections, encryption key management, virus and malware scanning, and almost every cryptographic protocol in current use. Without cryptographic hash functions, the internet would simply not work. At the same time, there isn't a good theory of hash functions. Unlike encryption algorithms, there are no secret keys involved; this makes it harder to mathematically define exactly what hash functions are.

The National Institute of Standards and Technology, NIST, is holding a competition to replace the SHA family of hash functions. "SHA" stands for "Secure Hash Algorithm." It was developed by the NSA in 1993 to replace the commercial MD4 and MD5 algorithms, and has been updated several times since then. All the SHA algorithms are very similar, and have been increasingly under attack, so NIST wants to replace them.

The competition is important because, unlike other technological standards, committee design — balancing the interests of diverse constituents — isn't conducive to good security. Security is best when it's designed by expert teams and then subjected to public review. And cryptography is best when it's chosen by competition.

In 1997, NIST held a competition for a block cipher to replace DES. Fifteen candidates and three-and-a-half years later, Rijndael became the new Advanced Encryption Standard — AES. NIST is doing the same thing for what it's calling SHA-3 (not, for some unexplained reason, the Advanced Hash Standard or AHS).

The deadline was October 31, and NIST received 64 submissions. This isn't surprising — I predicted 80 — as most of the 15 AES submitters were professors, whose students at the time have become professors themselves, with their own students. (If NIST does a stream cipher competition in another ten years, they should expect about 256 submissions.) These submissions came from academia, from industry, and from hobbyists. CIO magazine recently interviewed one of the submitters, who is 15. Twenty-eight submissions have been made public by the submitters, and six of those have been broken.

NIST is going through all the submissions right now, making sure they are complete and proper. Their goal is to publish all accepted submissions by the end of November, in advance of the First Hash Function Candidate Conference, to be held in Belgium right after the Fast Software Encryption workshop in February.

The group expects to quickly make a first cut of algorithms — hopefully to about a dozen — and give the community a year of cryptanalysis before making a second cut in 2010. After another year of cryptanalysis, NIST will choose a winner in 2011. Expect a final standard by 2012.

My advice for software developers is to let the process run its course. While it's tempting to use the new cool algorithms in your designs, it's far too soon to trust any of them. This process is likely to result in all sorts of new research results in hash function security, and some real cryptanalytic surprises. Give the community a few years to figure out which ones are good and which aren't.

I've previously called this sort of thing a cryptographic demolition derby: The last one left standing wins. But that's only partially true. Certainly all the groups will spend the next few years trying to cryptanalyze each other, but in the end there will be a bunch of unbroken algorithms. NIST will select one based on performance and features.

NIST has stated that the goal of this process is not to choose the best standard but to choose a good standard. I think that's smart; in this process, the best is the enemy of the good. While there's no rush to choose a new standard — the SHA-2 algorithms will remain secure for the foreseeable future — we don't want to analyze the candidates forever.

Personally, I was part of a group of eight cryptographers that submitted Skein to the competition. A decade ago, writing Twofish and participating in the AES process was the most fun I had ever had in cryptography. These next few years promise to be even more fun.

---

Bruce Schneier is chief security technology officer of BT. His new book is Schneier on Security.

District Court Holds that Running Hash Values on Computer Is A Search: The case is United States v. Crist, 2008 WL 4682806 (M.D.Pa. October 22 2008) (Kane, C.J.). It's a child pornography case involving a warrantless search that raises a very interesting and important question of first impression: Is running a hash a Fourth Amendment search? (For background on what a "hash" is and why it matters, see here).

First, the facts. Crist is behind on his rent payments, and his landlord starts to evict him by hiring Sell to remove Crist's belongings and throw them away. Sell comes a cross Crist's computer, and he hands over the computer to his friend Hipple who he knows is looking for a computer. Hipple starts to look through the files, and he comes across child pornography: Hipple freaks out and calls the police. The police then conduct a warrantless forensic examination of the computer:

In the forensic examination, Agent Buckwash used the following procedure. First, Agent Buckwash created an "MD5 hash value" of Crist's hard drive. An MD5 hash value is a unique alphanumeric representation of the data, a sort of "fingerprint" or "digital DNA." When creating the hash value, Agent Buckwash used a "software write protect" in order to ensure that "nothing can be written to that hard drive." Supp. Tr. 88. Next, he ran a virus scan, during which he identified three relatively innocuous viruses. After that, he created an "image," or exact copy, of all the data on Crist's hard drive.

Agent Buckwash then opened up the image (not the actual hard drive) in a software program called EnCase, which is the principal tool in the analysis. He explained that EnCase does not access the hard drive in the traditional manner, i.e., through the computer's operating system. Rather, EnCase "reads the hard drive itself." Supp. Tr. 102. In other words, it reads every file-bit by bit, cluster by cluster-and creates a index of the files contained on the hard drive. EnCase can, therefore, bypass user-defined passwords, "break down complex file structures for examination," and recover "deleted" files as long as those files have not been written over. Supp. Tr. 102-03.

Once in EnCase, Agent Buckwash ran a "hash value and signature analysis on all of the files on the hard drive." Supp. Tr. 89. In doing so, he was able to "ingerprint" each file in the computer. Once he generated hash values of the files, he compared those hash values to the hash values of files that are known or suspected to contain child pornography. Agent Buckwash discovered five videos containing known child pornography. Attachment 5. He discovered 171 videos containing suspected child pornography.

One of the interesting questions here is whether the search that resulted was within the scope of Hipple's private search; different courts have approached this question differently. But for now the most interesting question is whether running the hash was a Fourth Amendment search. The Court concluded that it was, and that the evidence of child pornography discovered had to be suppressed:

The Government argues that no search occurred in running the EnCase program because the agents "didn't look at any files, they simply accessed the computer." 2d Supp. Tr. 16. The Court rejects this view and finds that the "running of hash values" is a search protected by the Fourth Amendment.

Computers are composed of many compartments, among them a "hard drive," which in turn is composed of many "platters," or disks. To derive the hash values of Crist's computer, the Government physically removed the hard drive from the computer, created a duplicate image of the hard drive without physically invading it, and applied the EnCase program to each compartment, disk, file, folder, and bit.2d Supp. Tr. 18-19. By subjecting the entire computer to a hash value analysis-every file, internet history, picture, and "buddy list" became available for Government review. Such examination constitutes a search.

I think this is generally a correct result: See my article Searches and Seizures in a Digital World, 119 Harv. L. Rev. 531 (2005), for the details. Still, given the lack of analysis here it's somewhat hard to know what to make of the decision. Which stage was the search — the creating the duplicate? The running of the hash? It's not really clear. I don't think it matters very much to this case, because the agent who got the positive hit on the hashes didn't then get a warrant. Instead, he immediately switched over to the EnCase "gallery view" function to see the images, which seems to be to be undoudtedly a search. Still, it's a really interesting question.

Warnings About Financial Institutions and Derivatives

Risks of Financial Institutions
The nature of a financial institution is that there are a lot of ways to go to hell in a bucket. You can push credit too far, do a dumb acquisition, leverage yourself excessively---its not just derivatives [that can bring about your downfall].

Maybe it's unique to us, but we're quite sensitive to financial risks. Financial institutions make us nervous when they're trying to do well.

We're exceptionally goosey of leveraged financial institutions. If they start talking about how good their risk management is, it makes us nervous.

We fret way earlier than other people. We've left a lot of money on the table through early fretting. It's the way we are -- you'll just have to live with it.

Derivatives
The system is almost insanely irresponsible. and what people think are fixes aren't realy fixes. It's so complicated I can't do it justice here - but you can't believe the trillions of dollars involved. You can't believe the complexity. You can't believe how difficult it is to do the accounting. You can't believe how big the incentives are to have wishful thinking about values and wishful thinking about ability to clear.

People don't think about the consequences of the consequences. People start by trying to hedge against interest rate changes, which is very difficult and complicated. Then, the hedges make the [reported profits] lumpy. So they use the new derivatives to smooth this. Well, now you've morphed into lying. This turns into a Mad Hatter's Tea Party. This happens to vast, sophisticated corporations.

Somebody has to step in and say, "We're not going to do it - it's just too hard."

I think a good litmus test of the mental and moral quality at any large institutions [with significant derivative exposure] would be to ask them, "Do you really understand your derivatives book?" Anyone who says yes is either crazy or lying.

It's easy to see [the dangers] when you talk about [what happened with] the energy derivatives - they went kerflooey. When [the companies] reached for the assets that were on their books, the money wasn't there. When it comes to financial assets, we haven't had any such denouement and the accountings hasn't changed so the denouement is ahead of us.

Derivatives are full of clauses that say if one party's credit gets downgraded then it has to put up collateral. It's like margin - you can go broke [just putting up more margin]. In an attempt to protect themselves, they've introduced instability. Nobody seems to recognize what a disaster of a system they've created. It's a demented system. 

In engineering people have a big margin of safety. But in the financial world, people don't give a damn about safety. They let it balloon and balloon and balloon. It's aided by false accounting. I'm more pessimistic about this than Warren is.

Accounting for Derivatives
I hate with a passion GAAP [Generally Accepted Accounting Principles] as applied to derivatives and swaps. JP Morgan sold out to this type of accounting to front-end revenues. I think it's a disgrace.

It's bonkers, and the accountants sold out. Everyone caved, adopted loose [accounting] standards, and created exotic derivatives linked to theoretical models. As a result, all kinds of earnings, blessed by accountants, are not really being earned. When you reach for the money, it melts away. It was never there.

It [accounting for derivatives] is just disgusting. It is a sewer, and if I'm right, there will be hell to pay in due course. All of you will have to prepare to deal with a blowup of derivative books.

Likelihood of a Derivatives Blowup
We tried to sell Gen Re's derivatives operations and couldn't, so we started liquidating it. We had to take big markdowns. I would confidently predict that most of the derivatives books of [this country's] major banks cannot be liquidated for anything like what they're carried on the books at. When the denouement will happen and how severe it will be, I don't know. But I fear the consequences could be fearsome. I think there are major problems, worse than in the energy field, and look at the destruction there.

I'll be amazed if we don't have some kind of significant [derivatives-related] blowup in the next five to ten years.

I think we're he only big corporation in America to be running off its derivative book.

It's a crazy idea for people who are already rich -  like Berkshire - to be in this business. It's a crazy business for big banks to be in.

Yo would be disgusted if you had a fair mind and spent a month really delving into a big derivative operation. You would think it was Lewis Carroll. You would think it was the Mad Hatter's Tea Party. And the false precision of these people is just unbelievable. They make the worst economics professors look like gods. Moreover, there is depravity augmenting the folly. Read the book F.I.A.S.C.O., by law professor and former derivative trader Frank Partnoy, an insider account of the depravity of derivative trading at one of the biggest and best-regarded Wall Street firms. This book will turn your stomach.

I'm not complaining about the fact that I can't see what I'm typing. I understand and laud that feature, because I don't want someone looking over my shoulder at the password I'm typing, and this even applies when I'm at home. I love my children, but I certainly don't want them knowing the password to my bank account!

No, what I'm bothered by is how a typical password text box behaves on a form that may incur multiple post-backs before it's finally submitted. If you use the built in ASP.NET TextBox control, it purposely does not repopulate the password text, which means if you press a button on the form that performs a post-back, or if you have a multi-page form that posts back on every step, that password disappears, and the user typically has to re-enter it. You could solve this with liberal use of ASP.NET Ajax UpdatePanels, but that adds its own complexities. I wanted a simpler solution.

So I did a little research to see what others had discovered about this problem, and I ended up deriving my own custom control from TextBox to make a much more user-friendly (and developer-friendly) TextBox control. I called it PasswordTextBox, and it acts just like a TextBox in password mode, but it retains the password while still giving the user the same level of protection the standard TextBox supplies.

My PasswordTextBox operates very simply: it stores the password in control state, and renders a series of fixed characters (with the same length as the actual password) into the text box so that it "looks" like the user's password has been rendered. Since control state is part of view state, and since view state is stored in a hidden field on the form, I encrypt the password before putting it into control state.

The result is quite nice - the user can post your form back as many times as she needs to, perhaps moving back and forth across wizard steps or tabs, and when she finally presses the "Finish" button (or whatever you call the last step of your input form), your code will be able to read the password by simply accessing the Text property on the PasswordTextBox. The user will believe that her password is sitting there on the form while she's working, as the same number of obfuscated characters will show up in the field as she typed in originally (what she doesn't know is that those characters aren't her real password anymore, but what she doesn't know won't hurt her!)

Note that to keep this simple, I used DPAPI to encrypt the password, which suited my purposes. But if you have a web farm, that won't work well at all if you don't know which machine the user's going to post back to, so you'll want to replace that with something more robust. I could see looking up the <machineKey> for entropy, as that tends to be sync'd already across the farm, but I've not yet spent the cycles to go down that road, since unfortunately all of the code for generating keys based on that config section are off limits in ASP.NET (most of the useful stuff is marked internal). I don't think it'd be that hard to do though.

Anyway, without further ado, here's the code, which you'll see is quite simple. I'd love feedback, especially if you see any glaring problems with the idea or the implementation!

public class PasswordTextBox : TextBox
{
    // unlikely that a string of these would be used for a password
    const char PasswordPlaceholderChar = '}';

    string password; // stored encrypted in control state

    protected override void OnInit(EventArgs e)
    {
        base.OnInit(e);
        Page.RegisterRequiresControlState(this);
    }

    protected override object SaveControlState()
    {
        byte[] encryptedPassword = ProtectPassword(password);

        object baseControlState = base.SaveControlState();
        if (null == baseControlState)
            return encryptedPassword;
        else return new Pair(baseControlState, encryptedPassword);
    }

    protected override void LoadControlState(object savedState)
    {
        byte[] encryptedPassword;

        Pair pair = savedState as Pair;
        if (null != pair)
        {
            base.LoadControlState(pair.First);
            encryptedPassword = pair.Second as byte[];
        }
        else encryptedPassword = savedState as byte[];

        password = UnprotectPassword(encryptedPassword);
    }

    /// <summary>
    /// This control always uses TextMode=Password
    /// </summary>
    public override TextBoxMode TextMode
    {
        get
        {
            return TextBoxMode.Password;
        }
        set { }
    }

    /// <summary>
    /// TextBox doesn't render value attribute for TextMode=Password
    /// So we add code that renders a placeholder text instead
    /// </summary>
    /// <param name="writer"></param>
    protected override void AddAttributesToRender(HtmlTextWriter writer)
    {
        base.AddAttributesToRender(writer);

        string text = Text;
        if (text.Length > 0)
            writer.AddAttribute(HtmlTextWriterAttribute.Value,
                GetPlaceholderPassword(text));
    }

    /// <summary>
    /// TextBox doesn't save the "Text" viewstate in
    /// TextMode=Password and we don't want our behavior to break
    /// if ViewState is turned off so we store the password in
    /// Control State, encrypted with MachineKey
    /// </summary>
    public override string Text
    {
        get
        {
            return password ?? string.Empty;
        }
        set
        {
            // this prevents us overwriting the actual
            // password with a placeholder
            if (!string.IsNullOrEmpty(password) &&
                value.Equals(GetPlaceholderPassword(password)))
                return;

            password = value;
        }
    }

    private string GetPlaceholderPassword(string realPassword)
    {
        int length = 12;
        if (!string.IsNullOrEmpty(realPassword))
            length = realPassword.Length;

        StringBuilder sb = new StringBuilder();
        sb.Append(PasswordPlaceholderChar, length);

        return sb.ToString();
    }

    public byte[] ProtectPassword(string password)
    {
        if (string.IsNullOrEmpty(password))
            return null;
        byte[] cleartext = Encoding.UTF8.GetBytes(password);
        return ProtectedData.Protect(cleartext, null,
            DataProtectionScope.LocalMachine);
    }

    public string UnprotectPassword(byte[] ciphertext)
    {
        if (null == ciphertext)
            return null;
        byte[] cleartext = ProtectedData.Unprotect(ciphertext, null,
            DataProtectionScope.LocalMachine);
        return Encoding.UTF8.GetString(cleartext);
    }
}