Research: Auto-detection of Compressed Files in Apple’s macOS


Compressed files on macOS are autodetected by the operating system even if they are renamed to certain other extensions. This can be used to fool users and antivirus software that relies on file extensions by packaging malicious code inside compressed files with different extensions. The vendor (Apple) does not consider this to be a security issue. Most anti-virus vendors for macOS are not affected by this issue. This was originally discovered in macOS v10.11 (El Capitan) and v10.12 (Sierra), but the latest version of macOS v10.13 (High Sierra) was not tested.


[NOTE: This bug was originally discovered as a result of a different set of bugs in Google’s Chrome browser. While the impact of this particular issue isn’t high, it was interesting enough for us to pursue a coordinated disclosure process. Because of the large number of parties involved, the disclosure coordination process took a long time which is why this article took almost two years to publish.]

On Microsoft Windows, files are identified by their extensions, which appears after the “.” in the filename. On macOS metadata about the file maybe available separately and either a creator code, a type code or a Uniform Type Identifier is used. However, on the Internet (in browsers and email clients) instead of filenames, MIME media types are used with a registry maintained by IANA on behalf of the IETF. Linux systems use a mix of extensions and media types, with some auto-detection / “sniffing” of media types based on file content. Some mappings do exists across the various systems as well.

For example, a ZIP archive would be identified as follows:

  • Windows – .zip extension
  • Internet/Linux – application/zip media type
  • macOS UTI –

Additionally, on most desktop OSes, an association exists between a file type and an application that will open it by default. Those associations are maintained differently from OS to OS, but at their core they associate a particular identifier about a file type such as an extension (Windows) or a media type (browsers), and a program assigned to open it by default. Users are used to this arrangement and many security utilities such as antivirus programs will only look inside files that maybe dangerous. For example, a ZIP file on Windows if renamed to a different extension may not necessarily be scanned by default because double clicking on it will not open it.

Another important point is that malware authors may sometimes try to disguise malicious code by compressing it inside an archive such as a ZIP file. The expectation is that when a user downloads it, they will double click and open it using the default program on that platform, and then will execute the malicious code. This is another reason why this functionality deserves a closer look.


The following two things were discovered:

  1. The compression utility that is part of macOS will open any file extension associated with that program and will try to “sniff” / auto-detect the original file type used. The following file extensions were tested:
    • ZIP Files when renamed as:
      • .AS
      • .CPGZ
      • .PAX
      • .XIP (a Gatekeeper warning will be shown for non-signed files)
    • DMG files when renamed as:
      • .CDR
      • .DART
      • .DC42
      • .DISKCOPY42
      • .DMG
      • .DMGPART
      • .DVDR
      • .IMG
      • .IMGPART
      • .ISO
      • .NDIF
      • .SMI
      • .TOAST
      • .UDIF
  2. The OS itself (macOS) itself will open and execute some file formats even when renamed to a different extension. Gatekeeper protection is not bypassed. The following extensions are affected:
    • PKG
    • MPKG

To duplicate the first issue, create a ZIP file containing any content (we used the EICAR test file) and rename to include a file extension as any of the compression formats above for ZIP. (AS, CPGZ, PAX or XIP). Send this file to a macOS computer via USB or email or a link; download and double click. The ZIP file will open correctly. You can also do the same thing but with a DMG file for any of the DMG file formats listed above (DC42, ISO, etc).

To duplicate the second issue, create a PKG file containing some code or take an existing one, rename as .MPKG and transfer to a macOS computer. Double click to execute.

All testing was done in May 2016 on a MacBook Pro running MacOS v10.11.3 (El Capitan), and re-tested again in April 2017 on a MacBook running MacOS v10.12.04 (Sierra). It is unclear whether later versions of MacOS are affected since we did not perform testing on versions past v10.12.04 (Sierra).


There are two issues:

  1. Human users and anti-malware software are not aware that macOS supports a large number of legacy compression file types and may not be properly looking out for them or scanning them.
  2. Because of the “sniffing” behavior, it would be trivial for an attacker to package malware inside a well known format like ZIP or DMG rename it to one of these extensions. Anti-virus software may fail to scan such archives because they do not expect a ZIP file to be packaged that way.

The information in this article was originally discovered while analyzing Google’s Chrome browser (details here).

Our recommendations are as follows:

  • Apple should consider deprecating or adding a warning for these extensions and removing the “sniffing” support.
  • Anti-malware software for macOS should support all of these formats, as well as accounting for the possibility of one format being renamed as another

Vendor Responses

The vendor (Apple) does not consider this to be a security issue as follows:

After examining your report we do not see any actual security implications. All of the extensions provided in your report are supported disk image formats and will be treated equally.

After examining your report we do not see any actual security implications. Archive Utility opens archive files and the extensions you provided are archive extensions.

After examining your report we do not see any actual security implications. The Installer app makes it clear when executable code is running even if the file has been renamed.

As per advice of Apple’s security team, we also contacted multiple antivirus vendors that provide AV software for macOS to check if they are affected by this issue. Here is what we got back:

Vendors That Responded:

  • Avast – not affected
  • Avira – not affected
  • AVG – related bug for engine versions prior to 4668 has been fixed earlier (see CVE-2017-9977 and our blog post); other products not affected
  • BitDefender – not affected
  • Cisco – one product impacted, tracked by bug identifier CSCve34034 – no CVE has been issued:
    • Cisco AMP Virtual Private Cloud Appliance – The Cisco AMP appliance does not rely on the file extension when processing ZIP archives or PKG install packages. However, older versions relied on file extension to detect DMG files and so is susceptible to one of the scan evasion problems described in the advisory. The DMG portion is now fixed in software release 1.4.5.
  • ClamXAV (Canimaan Software) – not affected
  • Comodo – not affected
  • CyberByte – not affected
  • Dr. Web – not affected
  • ESet – not affected
  • F-Secure – not affected
  • Intego – not affected
  • Kaspersky – not affected
  • Malware Bytes – not affected
  • Protect Works – not affected
  • QuickHeal – not affected
  • Sophos – not affected
  • Symantec – not affected
  • Trend Micro – not affected
  • Webroot – not affected

Other Vendors:

  • 360 Total Security – pending
  • BullGuard – no response
  • EScanAV – no response
  • GData – pending
  • Google Chrome – safe browsing affected prior to M51 and M52 (see our blog post here)
  • MacKeeper – no response
  • McAfee – no response
  • Panda – no response
  • QuikAV – pending
  • Total Defense – pending


Apple Product Security Followup Numbers: 638059697,  640528823 and 640528841

Cisco Ref # PSIRT-1814664974


Advisory written by Yakov Shafranovich.

Timeline Summary

2016-03-21: Report # 638059697 submitted
2016-05-04: Reports # 640528823 and 640528841 submitted
2016-05-21: Report # 640528823 rejected
2016-06-22: Report # 638059697 rejected
2016-06-23: Report # 640528841 rejected

2017-03-15: Advisory provided to the vendor for comment
2017-04-23: Retested on macOS Sierra, updated and resent to vendor for comment
2017-04-28: Reply from vendor received
2017-05-01: Retested on a fresh install of macOS Sierra, revised advisory sent to vendor for comment
2017-05-01: Notifications go out to AV vendors

2018-01-24: Second time that notifications go out to AV vendors
2018-02-10: Third and final time that notifications go out to AV vendors
2018-02-10: Final advisory shared with the vendor (Apple) for comment
2018-02-25: Public disclosure

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