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Backward Compatibility Makes Windows Insecure

 & Neil J. Rubenking Principal Writer, Security

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First there was DOS, then Windows, then more and more versions of Windows. At every level, the new operating system absolutely had to support programs written in all but the most ancient old ones. As demonstrated in a talk today at the Black Hat security conference, this thirst for backward compatibility opens up huge possibilities for malicious software writers.

If you ever accidentally load a Windows EXE file into WordPad, you'll see it begins with the letters MZ. These are the initials of Mark Zbikowski, an early MS-DOS developer, and they go all the way back to the first DOS EXE files. A bit latter you'll see the letters PE, standing for Portable Executable. Mario Vuksan and Tomislav Perecin, founders of Reversing Labs, went into great detail about the many ways malefactors can misuse the PE file format.

The precise details of this pair's demonstration would be of interest only to experts, and a room full of experts ate up every word. The "malformations" they displayed all serve to help hide malicious code from static or dynamic analysis, so the malware can execute without being detected.

Microsoft can't just close the holes in the PE format, because many older programs would stop working. In addition, this PE format isn't limited to your PC. You'll find it in Windows CE, XBOX, ReactOS, and others. The presenters concluded that malware researchers simply need to be aware of all these possible malformations and take them into account when analyzing code.

For ordinary users, this will translate into improved security. If you're an expert who just happened not to be in the room, the full discussion is available here.

About Our Expert

Neil J. Rubenking

Neil J. Rubenking

Principal Writer, Security

My Experience

When the IBM PC was new, I served as the president of the San Francisco PC User Group for three years. That’s how I met PCMag’s editorial team, who brought me on board in 1986. In the years since that fateful meeting, I’ve become PCMag’s expert on security, privacy, and identity protection, putting antivirus tools, security suites, and all kinds of security software through their paces.

Before my current security gig, I supplied PCMag readers with tips and solutions on using popular applications, operating systems, and programming languages in my "User to User" and "Ask Neil" columns, which began in 1990 and ran for almost 20 years. Along the way, I wrote more than 40 utility articles, as well as Delphi Programming for Dummies and six other books covering DOS, Windows, and programming. I also reviewed thousands of products of all kinds, ranging from early Sierra Online adventure games to AOL’s precursor Q-Link.

In the early 2000s, I turned my focus to security and the growing antivirus industry. After years of working with antivirus, I’m known throughout the security industry as an expert on evaluating antivirus tools. I serve as an advisory board member for the Anti-Malware Testing Standards Organization (AMTSO), an international nonprofit group dedicated to coordinating and improving testing of anti-malware solutions.

The Technology I Use

Much of the testing I do, particularly testing with real-world ransomware, is just plain dangerous. To perform such tests safely, I sequester them inside virtual machines managed by VMWare Workstation. For cross-platform testing, I use a MacBook Air, a Google Pixel 4, and a 6th-generation iPad.

I rely on my Delphi coding skills to create and maintain small applications. These include programs to check whether an antivirus correctly handled the malware it detected, launch dangerous URLs and record the security program’s reaction, and analyze the malware that I collect for use in testing. I also wrote a tiny browser and text editor for use in testing security apps that have predefined reactions for known products.

I do my writing and research on a Dell OptiPlex desktop, relying on Microsoft Word (my fingers know all the shortcuts). Many of my articles include charts and analysis; Excel is my go-to for those. When work hours end, though, I escape the bounds of Microsoft and Windows. There’s an iPhone in my pocket, I relax with my oversized iPad, and my Kindle Oasis is always loaded with the best science fiction and fantasy.

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