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Windows 11 pulls ahead of Windows 10 in anti-phishing stakes

Some new security additions and changes have been announced for users of Windows, but you’ll have to be using Windows 11 to get the most out of them. Windows 10 users may find that this is going to be a case of falling behind the herd ever so slightly.

Anti-phishing tools

Enhanced phishing protection, by way of Smartscreen, is the name of the game, and Microsoft is all too happy to explain the changes. Smartscreen is a Windows feature which helps ward off bogus sites phishing for personal data and payment information. People running IE8 and later will also find it attempts to protect against infectious files. It offers slightly different features depending on which flavour of Microsoft browser you’re using, but the overall end result is largely the same: A variety of protections against phishing portals.

In terms of features for Windows 11, enhanced phishing protection “automatically detects when users type their password into any app or site”. Windows knows “in real time” whether websites and apps have secure connections to trusted websites, notifying users of potential danger up ahead and also spreading word to other users when a phishing attack is blocked.

There is also mention of Windows analysing when and where password entry occurs, notifying users of potentially unsafe usage. This sounds a lot like how many password managers operate, popping a notification when (for example) password reuse is detected. One key difference here is that using passwords in an unsafe way is “reported to IT” for incident tracking purposes.

Friendly popups

There are some interesting additions to the user experience. Typing a password into a phishing site in a Chromium browser, or an application connecting to a phishing portal, presents the user with a popup which says:

This app made an unsafe connection that was reported to Microsoft for stealing passwords. Your organisation recommends changing your work or school password to keep your account safe.

Clicking the change password button takes users to sign-in options where they can alter the password as needed. Microsoft says that without this feature, credentials may be handed over to the fake site. On the other hand, popups that lead people from dangerous sites to password amendment options may encourage malicious imitations that trick unwary users. However, two sets of popups might increase the chances of something untoward being noticed, but the history of UX is littered with intolerant users blazing through that sort of thing.

Elsewhere, Windows will notify users who are typing passwords into notepad files and other programs that this is bad practice. As per the relevant popup:

It’s unsafe to store your password in this app. Your organisation considers it unsafe to store your password in this app and recommends removing your password from this file.

We’re not here today to discuss the merits and drawbacks of off-the-beaten-track password systems. However, it’s worth noting that this detection of typed passwords is raising some eyebrows:

Windows 11, but not 10

Finally, we come to the part where our two operating system paths diverge.

Custom-made phishing alerts are available to Windows 11 users, but not to users of Windows 10. Organisations can configure Enhanced Phishing Protection to warn uses about password reuse, unsafe apps, and malicious activity, and can and switch the feature’s audit mode on and off, which determines whether sends telemetry about unsafe password events.

It’s to be expected that Windows 11 will eventually pull away from 10 in the security frontrunner stakes. Although adoption was low at the tail end of 2021, numbers will slowly ramp up over time as the Windows 10 end-of-life approaches, and organisations catch up with the stringent hardware requirements.

Only a few months back, we saw Microsoft tackling RDP intrusion with rate limiting for login attempts. We also now have upgrades to kernel protection, more support for hybrid work operations, and new default limits for SMB server authentication. It’s inevitable that we’ll continue to see this happening, and so the gulf will widen between the OS siblings.

No matter which version you’re running, ensure you keep your OS fully up-to-date and enable the security options most relevant to you. There’s enough choice available to hopefully configure your devices the exact way you need them to be running at any given time.

Stay safe out there!


Christopher Boyd

Former Director of Research at FaceTime Security Labs. He has a very particular set of skills. Skills that make him a nightmare for threats like you.