The changing security environment with Microsoft 365

First, a quick trip down memory lane. Back when Microsoft released Windows XP it had no local firewall (yep, I know, hard to believe now). After that fact being exploited by malicious software to spread through networks, Microsoft added a firewall to Windows XP in Service Pack 1. However, it didn’t automatically enable it. It remained something optional that was on the user to enable. Of course, given that most people are never going to enable a security feature that is optional, security issues continued. Then, with Service Pack 2, Microsoft enabled the firewall in Windows XP and it has been on ever since.

Most software is generally not configured as securely as it could be out of the box. In the case of Microsoft, it has to cater to a very, very broad audience with very different needs and configurations. Thus, it has fallen to the IT Professional for the business to implement the appropriate security using the features provided.

This equates to the Windows XP Service Pack 1 days. That is, the security capabilities are included but not enabled. And just like those days, only a very small percentage of them seem to get implemented. Multi Factor Authentication (MFA) is a great example of this. From Microsoft Ignite 2019 (i.e ONLY last year):

“it was discussed that out of all the Azure tenants globally, less than 8% of them WORLD-WIDE have enabled MFA.  99.9% of attacks on accounts are prevented by MFA.” – Reference

Even though EVERY Microsoft/Office 365 and Azure tenant includes MFA for identities, less than 8% have enabled it. This is hard to rationalise given the reality that doing so would prevent almost 100% of attacks. Clearly, it harkens back to the Windows XP Service Pack 1 days – if it ain’t on by default, then it will probably NEVER be turned on, no matter how much protection it provides.

So I hope you can appreciate, that in one aspect the IT security landscape hasn’t changed much from back when we had Windows XP (2002 if you check Wikipedia). I think however that this is in fact driving what I see as the ‘new’ security landscape for Microsoft 365.

The first big change with Microsoft 365 security is that Microsoft is beginning to move from Windows XP Service Pack 1 approach to a Service Pack 2 approach. That is, security enabled by default.

The first example of this is the End of support for Basic authentication and actively disabling it which you can read about here:

Deferred end of support date for Basic Authentication in Exchange Online

The next example is Security defaults.

Security defaults make it easier to help protect your organization from these attacks with preconfigured security settings:

  • Requiring all users to register for Azure Multi-Factor Authentication.
  • Requiring administrators to perform multi-factor authentication.
  • Blocking legacy authentication protocols.
  • Requiring users to perform multi-factor authentication when necessary.
  • Protecting privileged activities like access to the Azure portal.

If your tenant was created on or after October 22, 2019, it is possible security defaults are already enabled in your tenant. In an effort to protect all of our users, security defaults is being rolled out to all new tenants created.

and from – Introducing security defaults

“We will expand first to apply security defaults to all new tenants as well as applying it retroactively to existing tenants who have not taken any security measures for themselves.”


The next example are the new templated Exchange Online policies found in the Administration console which I have detailed previously here:

New templated email policies


Basically, this is a ‘Microsoft Security Baseline’ for securing Exchange online to best practices. You can read more about these at:

Preset security policies in EOP and Office 365 ATP

I can see a future where at least the Standard protection policy is applied to all new tenants out of the box.


Next, if you go and look in Microsoft EndPoint Manager you will see a growing number of similar baseline policies. I say growing, because a

New Security baseline for Office

is on the way.

At the moment, the smart approach is to use these baseline policies from Microsoft and then adjust or add as required to suit your own environment (i.e. Windows XP Service Pack 1 approach). Again, I see the day, in the not too distant future, where these baselines will be enabled by default (i.e. Windows XP Service Pack 2 approach).


Where I see a major difference between the Windows XP Service Pack 2 approach (i.e. security on by default) is with the introduction of Artificial Intelligence (AI). Thanks to telemetry from tenants and activities being fed back into the Microsoft Cloud, AI and Machine Learning (ML) can be used to look for anomalies. The best example of this Azure Sentinel.

In this new world of AI, you need to spend less time looking at individual events. In essence, you allow the AI to do that and determine what looks suspect based on EVERYTHING it sees in your environment and what it sees across the whole ecosystem. I can see a future where not only will the AI analyse all this data in a blink of the eye but it will also start taking action. For example, if you haven’t disabled basic authentication, it will disable it automatically because it knows that doing so is recognised by its algorithm to protect data to a high degree. I also believe we will also soon have the option for the AI to start taking ‘pro-active’ action to re-configure spam filtering to provide the best protection and adapt automatically to new methods of attack.

In short, I see a day, in the not to distant future, when all possible security options will be enabled by default and then AI will not only monitor but automatically adjust services and settings as required to meet the changing threat landscape. All of this will be driven by the growing volumes of telemetry that Microsoft collects from tenants big and small.

This all seems pretty marvellous, having a self adjusting security posture but perhaps the bigger question to consider is, what role does the IT Professional who is supposed to be setting this security configuration up manually today play in this future? Does a role for manual IT security configuration exist in the future? If not, where will the opportunities be in the IT security realm?

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