Host Operating System Selection
- 1 Windows Hosts
- 1.1 Windows as Malware
- 1.2 Windows Analysis
- 2 macOS Hosts
- 3 Recommendation
- 4 GNU/Linux Hosts
- 5 References
Windows as Malware
The Free Software Foundation (FSF) is scathing in its analysis of Windows, due to the threats posed to personal freedoms, privacy and security. Regardless of the version being used the FSF classifies Windows as "malware", meaning the software is designed to function in ways that mistreat or harm the user.  
Windows Backdoors and User Freedoms
A number of conscious decisions by Microsoft severely limit user freedoms, as well as seriously undermining the security of the platform.
Table: Windows Backdoors and User Freedom Threats
|Encryption||Microsoft has backdoored its disk encryption [archive].|
|Forced Updates||Microsoft has a history of updating software without permission [archive]; this represents a universal backdoor to impose any changes they like.|
|Software Choice and Deletion|
|Trust||The German government does not trust that Windows 8 and the Trusted Platform Module (TPM) v2.0 is not a backdoored combination [archive].|
The supposition that proprietary software is free of grave bugs is demonstrably false. In fact, the popularity of Windows platforms on desktops actually increases the risk, as attackers target the near monocultural operating system environment with regularity, for example:
- The Wanna Decryptor ransomware attack [archive] spreading the globe at the time of writing is solely focused on Windows platforms.
- Flaws in Internet Explorer and Edge [archive] have previously allowed attackers to retrieve Microsoft account credentials.
- Point-of-sale terminals running Windows were previously taken over in order to collect customers' credit card numbers [archive].
- Windows uses weak or broken cryptographic verification methods like MD5 [archive] and SHA-1 [archive].
- Windows 7 and earlier versions do not provide a secure central repository for downloading software, meaning a host of people risk dangerous downloads from the Internet.
The following table highlights Microsoft technical actions that harm users of specific hardware or software.
Table: Windows Sabotage
|Platform and Hardware Support||
|Tiered Security||Microsoft has announced that starting with Windows 10, it will begin forcing lower-paying customers to test less-secure new updates [archive] before giving higher-paying customers the option of whether or not to adopt them.|
Microsoft often releases proprietary programs or updates that destabilize or reduce the utility of the user's system:
- Windows displays advertisements [archive] for Microsoft products and those of its partners.
- Windows inserts advertisements inside of File Explorer [archive] to constantly nag about paid subscriptions.
- As noted earlier, Microsoft repeatedly nags to install Windows 10.
- Microsoft has encouraged complaints to system administrators [archive] about not upgrading to Windows 10.
Table: Windows Surveillance Threats
|Telemetry and Personal Data||
In summary, Microsoft has grand ambitions that are centered around interference, backdoors, sabotage, surveillance, the curtailing of user freedoms, and practices which undermine platform security. On that basis, Windows is a platform incapable of being properly secured by those with a serious interest in anonymity.
Forfeited Privacy Rights
By now the reader should be convinced that just by using any version of Windows, the right to privacy is completely forfeited. Windows is incompatible with the intent of Whonix and the anonymous Tor Browser, since running a compromised Windows host shatters the trusted computing base which is part of any threat model. Privacy is inconceivable if any information that is typed or downloaded is provided to third parties, or programs which are bundled as part of the OS regularly "phone home" by default [archive].
The fact that there is no way to completely remove or disable telemetry requires further consideration. For instance, non-enterprise editions do not permit anyone to completely opt-out of the surveillance "features" [archive] of Windows 10. Even if some settings are tweaked to limit this behavior, it is impossible to trust those changes will be respected. Even the Enterprise edition was discovered to completely ignore privacy settings and anything that disables contact with Microsoft servers.
Any corporation which forces code changes on a user's machine, despite Windows updates being turned off many times before, is undeserving of trust.      Windows 10 updates have been discovered to frequently reset or ignore telemetry privacy settings.  Microsoft backported this behavior to Windows 7 and 8 [archive] for those that held back, so odds are Windows users are already running it.
Ignoring for a moment its own built-in malware, Windows is a pile of legacy code full of security holes that is easily compromised. Microsoft's willingness to consult with adversaries and provide zero days [archive] before public fixes are announced logically places Windows users at greater risk, especially since adversaries buy security exploits from software companies [archive] to gain unauthorized access [archive] into computer systems.  Even the Microsoft company president has harshly criticized adversaries for stockpiling vulnerabilities [archive] that when leaked, led to the recent ransomware crisis world-wide.
Microsoft updates also use weak cryptographic verification methods such as MD5 and SHA-1. In 2009, the CMU Software Engineering Institute stated that MD5 "...should be considered cryptographically broken and unsuitable for further use".  In 2012, the Flame malware exploited the weaknesses in MD5 to fake a Microsoft digital signature. 
Windows is not a security-focused operating system [archive]. Due to Microsoft's restrictive, proprietary licensing policy for Windows, there are no legal software projects that are providing a security-enhanced Windows fork. In contrast, the Linux community has multiple Freedom Software Linux variants that are strongly focused on security, like Qubes OS [archive].
Windows Software Sources
Before Windows 8, there was no central software repository comparable to Linux where software could be downloaded safely. This means a large segment of the population remains at risk, since many Windows users [archive] are still running Windows 7. 
On the Windows platform, a common way to install additional software is to search the Internet and install the relevant program. This is risky, since many websites bundle software downloads with adware, or worse malware. Even if software is always downloaded from reputable sources, they commonly act in very insecure ways. For example, if Mozilla Firefox is downloaded from a reputable website like
chip.de,  then until recently, the download would have taken place over an insecure, plain http connection.  In that case, it is trivial for ISP level adversaries, Wi-Fi providers and others to mount man-in-the-middle attacks and to inject malware into the download. But even if https is used for downloads, this would only provide a very basic form of authentication.
To keep a system secure and free of malware it is strongly recommended to always verify software signatures. However, this is very difficult, if not impossible for Windows users. Most often, Windows programs do not have software signature files (OpenPGP / gpg signatures) that are normally provided by software engineers in the GNU/Linux world. For this reason it is safe to assume that virtually nobody using a Windows platform is regularly benefiting from the strong authentication that is provided by software signature verification.
In contrast, most Linux distributions provide software repositories. For example, Debian and distributions based on Debian are using apt-get. This provides strong authentication because apt-get verifies all software downloads against the Debian repository signing key. Further, this is an automatic, default process which does not require any user action. Apt-get also shows a warning should there be attempts to install unsigned software. Even when software is unavailable in the distribution's software repository, in most cases OpenPGP / gpg signatures are available. In the Linux world, it is practically possible to always verify software signatures.
Freedom Software Superiority
Based on the preceding section and analysis, it is strongly recommended to learn more about GNU/Linux and install a suitable distribution to safeguard personal rights to security and privacy. Otherwise, significant effort is required to play "whack-a-mole" with Windows malware, which routinely subjects users to surveillance, limits choice, purposefully undermines security, and harasses via advertisements, forced updates, remote removal of applications without consent, and so on.
Open Source software [archive] like Qubes, Linux [archive] and Whonix ™ [archive] is more secure than closed source [archive] software. The public scrutiny of security by design [archive] has proven to be superior to security through obscurity [archive]. This aligns the software development process with Kerckhoffs' principle [archive] - the basis of modern cipher [archive]-systems design. This principle asserts that systems must be secure, even if the adversary knows everything about how they work. Generally speaking, Freedom Software projects are much more open and respectful of the privacy rights of users. Freedom Software projects also encourage security bug reports, open discussion, public fixes and review.
In a fashion similar to Windows platforms, Apple operating systems also pose many security and privacy threats.
Table: macOS Threats 
|User Control and Freedoms||
Based on the preceding sections and analysis, it is strongly recommended to learn more about GNU/Linux and install a suitable distribution that safeguards rights to secure and private computing. Otherwise, significant effort is required to play "whack-a-mole" with Windows and malware, which routinely subjects users to surveillance, limits choice, purposefully undermines security, and harasses via advertisements, forced updates, remote removal of applications without consent, and so on.
Use GNU/Linux on the host and prefer in-repository software that is automatically gpg-signed and installed from the distributor's repositories by the package manager. This is far safer than downloading programs from the Internet like Windows adherents are required to do.
Recommended GNU/Linux Distribution
For additional reasons to avoid Ubuntu or Ubuntu-derived distributions, expand this section.
Ubuntu's paltry contributions to the upstream Libre projects they heavily rely upon is a policy decision and not a coincidence. Canonical founder Mark Shuttleworth has stated: "It is absolutely true we have no interest in the core fundamentals of the Linux kernel, none whatsoever." 
Canonical only bothers to majorly contribute in any way when forking significant projects; for example, Wayland into Mir, GNOME into Unity , and .deb packages incompatible with Debian because of zstd compression.  This appears to be a consistent attempt to fragment the software stack to lock in users and put pressure on competing distributions and vendors.  
The Ubuntu Contributor License Agreement gives them complete power over patents that cover contributed code. Essentially they are granted the right to re-license this code under any license of their choice, including a proprietary one.
Ubuntu also has a history of treating staff in a hostile fashion. For example, the Kubuntu spin project lead was unilaterally removed without warning and contrary to wishes of his team members.  Canonical also pilfered donation funds originally meant for desktop spin projects (Kubuntu, Lubuntu and others). In Kubuntu's case, after funding was abruptly dropped, Blue Systems had to step in to save the popular project.  
Canonical has also been applying an absurd intellectual property (IP) policy over packages in its repositories for years. This resulted in claims that Canonical owns the copyright over any binaries compiled by their servers. After the FSF stepped in and arranged a resolution over a period of two years, the policy was amended to state that Canonical’s IP policy cannot override packages with GPL licenses. However, this now means that any package with a permissive license is now copyrighted by Canonical.  
Unfortunately, downstream forks based on Ubuntu cannot be relied upon either. For example, the popular Linux Mint distribution was threatened with being cut off from access to Ubuntu infrastructure unless they caved in to Canonical's binary licensing terms.  Since then, Linux Mint has developed a version based on Debian instead. Canonical's vague trademark and IP policy has become toxic for downstream distributions. Many have made the smart choice to re-base on Debian instead of Ubuntu over the years including Kali, Whonix ™  and others. 
A final major concern is Canonical's friendly relationship with Microsoft. This should make all GNU/Linux users uncomfortable, given Microsoft's strategy of "Embrace, Extend, Extinguish" with respect to Free Software. 
There are of course other options. See "Why don't you use <your favorite most secure operating system> for Whonix ™?" for analysis of alternatives.
- https://www.gnu.org/proprietary/malware-microsoft.en.html [archive]
- https://www.fsf.org/windows [archive]
- https://web.archive.org/web/20170609221304/https://forums.whonix.org/uploads/default/original/2X/0/004857ec71ff2e4b23c88bf596b6142373fe2879.jpg [archive]
- https://web.archive.org/web/20071011010707/http://informationweek.com/news/showArticle.jhtml?articleID=201806263 [archive]
- https://archive.fo/LffTy [archive]
- https://arstechnica.com/information-technology/2015/07/windows-10-updates-to-be-automatic-and-mandatory-for-home-users/ [archive]
- http://voices.washingtonpost.com/securityfix/2007/09/microsofts_stealth_update_come.html [archive]
- https://www.zdnet.com/blog/hardware/confirmation-of-stealth-windows-update/779 [archive]
- https://community.spiceworks.com/topic/1535835-win-10-update-resets-privacy-again [archive]
- This is especially true for users of Tor, who are regularly targeted in this fashion.
- https://en.wikipedia.org/wiki/MD5#cite_note-11 [archive]
- https://arstechnica.com/security/2012/06/flame-crypto-breakthrough/ [archive]
- https://www.chip.de/downloads/Firefox-64-Bit_85086969.html [archive] https://www.webcitation.org/6mgUDIObc [archive]
- In 2019,
chip.denow enforces https for its entire website.
- https://www.gnu.org/proprietary/malware-apple.en.html [archive]
- https://fix-macosx.com/ [archive]
- https://fixubuntu.com/ [archive]
- https://www.theinquirer.net/inquirer/news/2168086/canonical-linux-kernel [archive]
- https://ask.fedoraproject.org/en/question/25127/how-to-build-unity-in-fedora/ [archive]
- https://www.phoronix.com/scan.php?page=news_item&px=Ubuntu-Zstd-Deb-Packages [archive]
- https://mjg59.dreamwidth.org/25376.html [archive]
- https://www.linux-magazine.com/Online/Blogs/Off-the-Beat-Bruce-Byfield-s-Blog/Mir-vs.-Wayland-show-why-upstream-projects-matter [archive]
- https://kver.wordpress.com/2015/05/27/making-sense-of-the-kubuntucanonical-leadership-spat/ [archive]
- https://www.pcworld.com/article/2998647/operating-systems/kubuntus-founder-resigns-accuses-canonical-of-defrauding-donors-and-violating-copyright.html [archive]
- https://lists.ubuntu.com/archives/kubuntu-devel/2012-February/005782.html [archive]
- https://www.fsf.org/news/canonical-updated-licensing-terms [archive]
- https://mjg59.dreamwidth.org/37113.html [archive]
- https://forums.linuxmint.com/viewtopic.php?t=152450 [archive]
- https://mjg59.dreamwidth.org/45939.html [archive]
- https://www.zdnet.com/article/microsoft-and-canonical-partner-to-bring-ubuntu-to-windows-10/ [archive]
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