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Microsoft Details How Chinese Hackers Acquired Signing Key for Outlook Breach

The signing key was accidentally leaked through a 'crash dump' file, which was sent to a Microsoft computer connected to the internet, allowing the hackers to steal it.

 & Michael Kan Principal Reporter

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Microsoft says it’s uncovered the mystery to how suspected Chinese hackers acquired a digital signing key to pull off July’s Outlook breach that ensnared several US government agencies. 

According to Microsoft, the key was accidentally leaked when the company computer holding it crashed in April 2021. During the error, the machine generated a crash dump report, which failed to redact the key from the file due to a software bug. 

Microsoft added that company computers that hold such signing keys are “highly isolated,” and have been stripped of various internet services, such as email and video conferencing. However, the crash dump report ended up opening a hole in the security. The unredacted file was automatically passed to a Microsoft computer devoted to debugging, which also happened to be connected to the internet. 

This paved a way for the Chinese hackers to loot the digital key when they compromised a Microsoft engineer’s corporate account, although it remains unclear how this occurred.

“This account had access to the debugging environment containing the crash dump which incorrectly contained the key,” the company said in Wednesday’s report. “Due to log retention policies, we don’t have logs with specific evidence of this exfiltration by this actor, but this was the most probable mechanism by which the actor acquired the key.”

Stealing the key then allowed the suspected Chinese hackers to forge the authentication tokens to access customer emails on Microsoft’s Outlook service. That said, the signing key was originally designed for consumer Microsoft accounts—not the enterprise Outlook accounts that the hackers targeted. 

The problem is that Microsoft neglected to update a software library to automatically validate key signing signatures between consumer and enterprise accounts. “Developers in the mail system incorrectly assumed libraries performed complete validation and did not add the required issuer/scope validation,” Microsoft said. “Thus, the mail system would accept a request for enterprise email using a security token signed with the consumer key.” 

Microsoft issued the report as the company has come under criticism for failing to stop the Outlook breach. In July, Sen. Ron Wyden urged the Justice Department and the FTC to probe Microsoft, claiming the company suffered from “negligent cybersecurity practices” that puts its customers at risk. 

For example, Wyden faulted Microsoft’s internal and external audits for failing to catch the key signing vulnerability. Meanwhile, other cybersecurity experts have also weighed in and accused Microsoft of trying to deflect blame for the company's own past mistakes.

According to Microsoft’s report, the company has since cleared up the bugs and processes that allowed the Chinese hackers to orchestrate the breach. This has included bolstering the company’s detection systems to prevent sensitive material from being erroneously added to crash dump files. But time will tell if the company's report further fuels criticism of Microsoft's approach to security.

About Our Expert

Michael Kan

Michael Kan

Principal Reporter

My Experience

I've been a journalist for over 15 years. I got my start as a schools and cities reporter in Kansas City and joined PCMag in 2017, where I cover satellite internet services, cybersecurity, PC hardware, and more. I'm currently based in San Francisco, but previously spent over five years in China, covering the country's technology sector.

Since 2020, I've covered the launch and explosive growth of SpaceX's Starlink satellite internet service, writing 600+ stories on availability and feature launches, but also the regulatory battles over the expansion of satellite constellations, fights with rival providers like AST SpaceMobile and Amazon, and the effort to expand into satellite-based mobile service. I've combed through FCC filings for the latest news and driven to remote corners of California to test Starlink's cellular service.

I also cover cyber threats, from ransomware gangs to the emergence of AI-based malware. In 2024 and 2025, the FTC forced Avast to pay consumers $16.5 million for secretly harvesting and selling their personal information to third-party clients, as revealed in my joint investigation with Motherboard.

I also cover the PC graphics card market. Pandemic-era shortages led me to camp out in front of a Best Buy to get an RTX 3000. I'm now following how the AI-driven memory shortage is impacting the entire consumer electronics market. I'm always eager to learn more, so please jump in the comments with feedback and send me tips.

The Best Tech I've Had:

  • My first video game console: a Nintendo Famicom
  • I loved my Sega Saturn despite PlayStation's popularity.
  • The iPod Video I received as a gift in college
  • Xbox 360 FTW
  • The Galaxy Nexus was the first smartphone I was proud to own.
  • The PC desktop I built in 2013, which still works to this day.

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