Microsoft

5 Things To Check In Your Microsoft Intune for Apple iOS 17 and iPadOS 17 Configuration

Posted on by Adam Fowler

Welcome to another ‘5 Things To Check’ security blog post. This time we’re looking at iPhones and iPads. Do you let people BYOD their own mobile device and just let them consume email on it? Are you controlling which application(s) can connect to your tenant on unmanaged devices, and are you applying application management to prevent data going out of those controlled applications?

iOS/iPadOS hardening has a lot of similarity to SOE/Windows Client hardening these days. Although when iPhones first launched there were next to no controls or management, the platform has eventually progressed into one that can be tightly controlled and hardened. Just like Windows though, this doesn’t mean that the out of the box is the most secure, and you’ll have to review a bunch of settings. You’ll also notice the settings are a bit more ‘basic’ compared to Windows, but that doesn’t mean they’re any less important.

Unsurprisingly, there’s a large amount of configuration than can be applied to harden the mobile user’s experience in dealing with company data, as well as protecting the users themselves. Again, I’m basing my 5 picks off the Center for Internet Security’s (CIS) benchmark’s list of ‘CIS Apple iOS 17 and iPadOS 17 Intune Benchmark’ items (freely available for non-commercial use), and I’m picking 5 that I think are important and not configured by default. This doesn’t mean you should only implement these 5, but it’s a good start for awareness on how much consideration needs to go into hardening an environment and why you need to put the effort in.

The CIS benchmark is broken up into two sections: BYOD and Supervised (i.e. company owned) devices, so my picks will be items that are recommended in both scenarios.

1. Ensure “Block Siri while device is locked” is set to “Yes” (and the lock screen in general)

Some may argue that Siri should be blocked altogether, because you’re sending data that could be sensitive back to Apple, and it may occur without you knowing. In reality, many people working from home probably have an Apple, Google, or Amazon device listening to everything they’re doing on their Teams or Zoom call anyway. However, those devices should at least not be connected to corporate data – unlike their Apple phone or tablet. This is more about someone gaining access to the physical device, and potentially being able to find out information about the data the iPhone has saved on it, or has access to. There have also been past bypasses on using Siri on the lock screen to unlock the phone or access certain other areas without needing the phone properly unlocked, so it’s seen as an unnecessary risk to leave this on.

This also extends to other data that could be viewable while the phone is locked, such as ‘Ensure “Block Today view in lock screen” is set to “Yes”‘ as this can show items like meetings, and ‘Ensure “Block voice dialing while device is locked” is set to “Yes”‘ as voice dialling is a function unrelated to Siri (there’s several more settings around lock screen information too!). You don’t want someone that finds your phone being able to access these and several other areas. One thing I’d potentially disagree with on the CIS benchmark is configuring the ‘Ensure a “Lock Screen Message” has been set’ message. Their advice is to have a helpdesk phone number or email address. The problem with this is, it shows someone who finds the phone what company the phone belongs to, and might incentivise them to keep or sell the phone somehow. If someone finds a phone from either a big company, or a company they don’t like, or a competitor to their own company, that’s a risky scenario. I’d suggest it’s better to use Apple’s guide on how to deal with a lost phone https://support.apple.com/en-au/101593 and also use Intune to destroy anything company managed – it should all be synced anyway and easily replaceable.

In Intune, this configuration is called ‘Allow Assistant White Locked’

2. Ensure “Maximum minutes after screen lock before password is required” is set to “Immediately”

This one is a straight forward setting. When the device’s screen is locked, how long should it wait before letting you just unlock it without a passcode or Face Unlock. It appears that the default for this is ‘Immediately’ but this demonstrates the importance of locking down configuration using a MDM such as Intune. The maximum time configurable is 4 hours, which is a long time someone could put their device down somewhere or completely lose it, and have no protection from being unlocked. The minimum time beyond immediate is 1 minute, which doesn’t seem like much – but someone locking their phone and putting it down leaving a whole minute for someone to obtain the phone is a fair amount of time. This is one I’d like to see a 5 second option just so users who accidently lock their device have a tiny window to unlock it again without having to verify – especially for BYOD. Extra layers of protection can be put on work related apps anyway requiring another Passcode or biometrics unlock.

To look at this option on iOS, Tap ‘Settings’ > ‘Touch ID & Passcode’ or ‘Face ID & Passcode’ depending on the device > Require Passcode. This needs to be set to ‘Immediately’, but as mentioned above a user can just change this.

In Intune, iOS Configuration Settings, the Maximum Grace Period can be set to ‘0’ which means ‘immediately’.

3. Ensure “Block viewing corporate documents in unmanaged apps” is set to “Yes”

As per Microsoft Learn documentation iOS/iPadOS device settings in Microsoft Intune | Microsoft Learn , this setting prevents documents being viewed/opened/saved to non-managed apps. Although some users might find this frustrating that they can’t use their favorite personal program, it prevents data leakage. Many apps will have their own data storage solutions and it’s quite easy for a user to accidently save a document in the wrong place, potentially another cloud provider and to a different country. On top of that, the app itself may not have the same protections as the managed apps you provide. Does the company scrape the data of what the user is doing – document names, metadata, or do they even try to use their own AI solution to read and help the user edit the document, provide a summary, or other hot AI topics? All this needs to be controlled by keeping the data where you manage it as much as possible, and not letting users have an easy path of getting data out. Without something like Purview, there’s always ways of extracting data, but you need to both provide good native ways of working with the data, as well as preventing or slowing down other methods.

As noted on the documentation, this setting does block third party keyboards, but for the same reasons as above, this is a good thing. Keyboard apps may track what you’re typing in different ways and keep a dynamic suggested list of shortcut words you commonly use – maybe you want to keep that project codenamed ‘Order 66’ under wraps as much as possible.

In Intune, Device Restrictions configuration has the ‘Yes’ option for ‘Block viewing corporate documents in unmanaged apps:

4. Ensure “Block trusting new enterprise app authors” is set to “Yes”

As the little (i) next to this configuration states – “Removes the Trust Enterprise Developer button in Settings->General->Profiles & Device Management.”

This setting actually blocks users from being able to trust apps that aren’t downloaded from the app store. Maybe good for a developer trying to quickly test their own app, but for normal users this shouldn’t be necessary. You can probably imagine plenty of scenarios where a user may get tricked into installing an app through non-standard means (such as being emailed a PDF that says to unlock the PDF, please install this software) and giving an attacker an easy path of getting malicious code onto a device.

The title of this setting is a bit misleading, because it sounds like new app authors to the Apple App Store would be blocked, but that’s not the case. Apple have a stringent App approval process and arguably it may not be perfect, it’s still a much larger barrier than just a file downloaded anywhere from the internet.

The approach of ‘only install approved apps’ may work for Corporate Owned devices, but not BYOD.

This is configured in Intune under Device restrictions > General > Block trusting new enterprise app authors:

5. Ensure “Block screenshots and screen recording” is set to “Yes”

I don’t really like the user impact of blocking screenshots and screen recording, but it’s a Level 1 CIS profile item which is their lowest baseline security recommendations. To quote CIS:

Be practical and prudent.
Provide a clear security benefit.
Not inhibit the utility of the technology beyond acceptable means.

Based on this, what is the big issue with screenshots, where’s the security benefit? If you think about most users (including yourself) there’s probably a mess of screenshots somewhere. People rarely clean these up. Worse, they get treated as images/photos and will sync to potentially multiple cloud solutions – Apple’s native photo sync, OneDrive, Google, and many other apps/companies that monitor newly created images and sync them off somewhere. Although you can protect Outlook from being able to take screenshots from within Intune via application configuration, you can’t stop someone screenshotting in many other apps, and therefore can’t protect the data in that screenshot.

If someone wants to take a photo of their computer screen or phone screen you can’t stop them, but blocking screenshots makes the process more difficult and means it should only happen when really needed (or someone’s stealing data on purpose!) and you severely reduce the risk of confidential screenshots floating around many unprotected consumer cloud solutions.

I hope this list has been useful, and I’m sure iOS/iPadOS 18 and beyond will come out soon, but the above should be relevant for quite some time!

5 Things To Check In Your Microsoft Edge Configuration

Posted on by Adam Fowler

In what has now become a ‘5 Things To Check’ series, this time we’re looking at Microsoft Edge. The Center for Internet Security’s (CIS) Microsoft Edge benchmark is up to v2.0.0, so again I’ll pick my favourite 5 things listed, along with giving my own explanation of why they matter and other considerations.

By the way, did you know there’s now a whole ‘Policies for Microsoft Edge’ area of the Microsoft 365 admin center? More details on the Microsoft Edge management service here.

OK let’s jump into the top 5!

1. Ensure ‘Configure extension management settings’ is set to ‘Enabled: *’

Browser extensions can do a bunch of useful things, including potentially reading everything you do and sending it off to a third party. Even if it’s not for malicious purposes, your users certainly aren’t looking into what an extension does permission wise, and thinking about data sovereignty (I know there will be exceptions to this!). Just like any other app, extensions should be controlled and go through an approval process before they’re allowed on a work device. Moreso, the tie-in with using Microsoft Edge with a work profile to both be required to access certain resources, as well as pulling down policies automatically to configure the profile in a secure state goes a long way to providing a full secure experience.

By default, all users can install whatever extensions they like.

Microsoft have full documentation on how to manage Microsoft Edge extensions here Detailed guide to the ExtensionSettings policy | Microsoft Learn but this setting is the start of enabling it, and blocking all by default unless there’s an exception – which is why it’s being set to a wildcard *. Exceptions to the global block can be granted with the setting ‘Allow specific extensions to be installed.’. There’s several ways to manage and deploy this:

Group Policy – https://learn.microsoft.com/en-us/deployedge/microsoft-edge-manage-extensions-policies#allow-or-block-extensions-in-group-policy

Intune – https://support.imperosoftware.com/hc/en-au/articles/10590384691347-Managing-Edge-extensions-in-Microsoft-InTune

Microsoft Edge management service (the new way!) https://learn.microsoft.com/en-us/deployedge/microsoft-edge-management-service#manage-settings-for-all-extensions

Yes there is management overhead in blocking all extensions and looking at each case on what you should allow, and yes you need to consider other browsers like Google Chrome – you can’t just lock down Microsoft Edge and leave Google Chrome to be a free for all, or users will go there instead.

2. Ensure ‘Enable profile creation from the Identity flyout menu or the Settings page’ is set to ‘Disabled’

I called out profiles in the first tip – Edge profiles are a core component of Microsoft Edge security. A work or school account signed into Microsoft Edge can pull down Microsoft 365 tenant settings, including the new Microsoft Edge Management Service which to quote the start of the learn.microsoft.com article:

The Microsoft Edge management service is a platform in the Microsoft 365 admin center that enables admins to easily configure Microsoft Edge browser settings for their organization. These configurations are stored in the cloud and the settings can be applied to a user’s browser through group assignment or group policy. Users must be logged into Microsoft Edge to retrieve these settings.

https://learn.microsoft.com/en-us/deployedge/microsoft-edge-management-service

Either Single Sign-on should enforce Edge to automatically sign in with the same account as the PC is logged in as, or on BYOD the requirement to create a profile with the work account can allow for application management – things like stopping data exiting the browser session, screenshots, the blocking of extensions etc.

On the flip side, letting users create profiles throws all that security and control out the window. If someone can create a new profile even as a guest, a lot of the controls drop off – as well as potentially treating the browser session as a consumer one, and things like Microsoft Rewards turn up. You also have history, bookmarks, password managers etc potentially being saved against a Microsoft account (rather than a work/school one). That Microsoft account may not even have MFA on it – so a compromised Microsoft account used to sync browser information could grab a lot of company related data if it’s being used for the wrong purposes.

The setting can be set by Group Policy if you download the Microsoft Edge for Business pack (worth doing if you’re living in Group Policy land still) – Download Edge for Business (microsoft.com), or the registry setting:

[HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Edge]
“BrowserAddProfileEnabled”=0

You can also set this via Microsoft Edge management service https://admin.cloud.microsoft/#/Edge/PolicyConfiguration/

3. Ensure ‘Enable AutoFill for addresses’ is set to ‘Disabled’

Ever walked up to an iPad at a business that you need to register your details on, and as you click on the first part of the form it shows you a bunch of other people’s data? That’s AutoFill enabled by default, when it definitely should not be.

This is a tough one, because AutoFill is so handy. You go to a website and need to fill in a form, but instead you get a dropdown, pick your name and the form is mostly filled out! In a work environment though, this can be a big catch. Are you ever putting in personally identifiable information for someone else? It could be as simple as an email address. That data gets saved in a manner that isn’t that much different to having a text file in your profile that contains the same data – so it shouldn’t be allowed.

You’d probably get user pushback on this, but a decent password manager should also have AutoFill functionality, but where it prompts you before it saves the data, and it’s easily readable against a profile rather than the more obfuscated method that Edge (and other browsers) generally use.

The AutofillAddressEnabled is easy to disable via registry, Group Policy with Download Edge for Business (microsoft.com) or via Microsoft Edge management service (and untick that ‘Allow users to override’ option which is ticked by default!).

4. Ensure ‘Prevent bypassing of Microsoft Defender SmartScreen warnings about downloads’ is set to ‘Enabled’

Microsoft Defender SmartScreen

Microsoft’s support site explains to users about Defender SmartScreen, including the Screening downloads part. Seems like a pretty good idea, if a user downloads something and it matches a file that Microsoft has already found unsafe, it’ll warn you:

Screening downloads: SmartScreen checks your downloads against a list of reported malicious software sites and programs known to be unsafe. If it finds a match, SmartScreen warns you that the download has been blocked for your safety. SmartScreen also checks your downloaded files against a list of well-known and popular downloads by Microsoft Edge users and warns you if your download is not on this list. 

https://support.microsoft.com/en-au/microsoft-edge/how-can-smartscreen-help-protect-me-in-microsoft-edge-1c9a874a-6826-be5e-45b1-67fa445a74c8#:~:text=Screening%20downloads%3A%20SmartScreen%20checks%20your,been%20blocked%20for%20your%20safety.

You can just bypass this warning and download the file anyway. A home user may want this experience to make the decision themselves, but this probably isn’t the decision you want an end user to make in a corporate environment and on a work device. Arguably, several other layers should protect you anyway including Defender for Endpoint or whatever EDR solution is in place, but this is a pretty safe extra layer to have in place.

Preventing user bypass of a SmartScreen detected suspicious download seems like an obvious one. Again, PreventSmartScreenPromptOverrideForFiles is a single setting via registry, Group Policy, or Microsoft Edge management service:

5. Ensure ‘Enhance the security state in Microsoft Edge’ is set to ‘Enabled: Balanced mode’

This is disabled by default. Clicking the ? next to ‘Enhance your security on the web’ will tell you:

What is enhanced security mode?
This runs your unfamiliar sites without the just in time (JIT) compilation to provide added protection. Running JIT-less reduces attack surface, making it difficult for malicious sites to exploit.
The additional protection includes Windows operating system mitigations such as Hardware Enforced Stack Protection, Arbitrary Code Guard (ACG), and Control Flow Guard (CFG).

Although there is a caveat ‘Most sites work as expected’, it’s an adaptive setting that learns behavour and what’s common the more it gets used. Admins can also add exceptions or forced enhanced security to certain sites: Browse more safely with Microsoft Edge | Microsoft Learn

I’ve been running this setting on at home for several months and haven’t noticed any issues, but I’m sure there are some sites that would be affected by this. You can decide if you let users toggle the option off on a per-website basis too.

The ‘Balanced mode option under ‘EnhanceSecurityMode’ setting can be set via registry, Group Policy with Download Edge for Business (microsoft.com) or via Microsoft Edge management service:

Bonus because I couldn’t pick between this and #5!
6. Ensure ‘Allow personalization of ads, Microsoft Edge, search, news and other Microsoft services by sending browsing history, favorites and collections, usage and other browsing data to Microsoft’ is set to ‘Disabled’

This is enabled by default. Regardless of trust in Microsoft or not, unnecessarily sending information such as browser history, favorites/collections etc is worth blocking. At the cost of ad personalisation, which should be irrelevant in a corporate setting. Enable this one!

The PersonalizationReportingEnabled setting is easy to disable via registry, Group Policy with Download Edge for Business (microsoft.com) or via Microsoft Edge management service:

It’s also worth calling out that Microsoft have their own Security Baseline for Microsoft Edge included in this: Download Microsoft Security Compliance Toolkit 1.0 from Official Microsoft Download Center which lists out all the policies with recommended settings, along with a bunch of other products. You should be keeping track of the Security Baseline for Microsoft Edge and following the guidance where possible on each release.

5 Things To Check In Your Intune for Windows 11 Configuration

Posted on by Adam Fowler

After receiving a lot of great feedback on my post 5 Things To Check In Your Microsoft 365 Tenant, I thought I’d do another post, picking my top 5 items from the Center for Internet Security’s (CIS) benchmark Microsoft Intune for Windows 11 Benchmark v3.0.1

This is a really big list to pick from, much bigger than the Microsoft 365 one – the document is over 1000 pages! Also you may look at this list and say ‘What has this got to do with Intune, I can apply these settings to any Windows 11 PC?’ – This is true, but the options CIS has laid out are ones that are natively available in Intune and therefore easily deployable. I’m also going to spend more time explaining the meaning behind the setting rather than telling you how to do it, as the CIS documentation (again freely avaialable for non-commerical use) clearly explains the setting and how to configure it.

Again these 5 things are important and I’ve tried to pick items that aren’t in the secure state by default, so I hope you find something new (or at least reassured!).

1. Ensure ‘Turn off access to the Store’ is set to ‘Enabled’

By default, any Windows 11 PC has the Microsoft Store enabled, the app installed, and a user can use it to obtain any software available in the store. I’ll avoid the whole ‘are Microsoft Store apps safe’ as I’m not privy to Microsoft’s application monitoring regime, just like Google’s Google Play or Apple’s App Store – but just like blocking users from installing software from other sources and methods, the Microsoft Store should be controlled in a corporate environment. There’s an entire history behind the Microsoft Store for Business and Microsoft Store for Education which is being replaced by packaging the apps in Intune for Microsoft Store which is still a work in progress with original retirement planned for 2023 being postponed.

All this leads to this one setting, which is just preventing the user being prompted the Windows Store as an option to find a program to open a file or protocol that currently has no association (for example, a user found a data.db file and tries to open it). They’ll see this dialog:

Either enable the confusingly named Intune setting ‘Turn off access to the Store’ (due to it only doing the below, which it describes in the details of the setting) or use this registry setting to remove the Microsoft Store option for any ‘open with’ dialog – Turn off access to the Store (admx.help)

Simple, but it ticks the box of a user complaining that they just followed what the computer told them to do when they end up with some wacky or weird solution obtained from the Microsoft Store that they start entering company data into. It also ties into a bigger piece around how you handle the Microsoft Store as a whole. I also found this blog post which goes into great detail about the Microsoft Store and how to control it, including the above setting: Restricting or blocking access to the Microsoft Store (call4cloud.nl)

2. Ensure ‘Backup Directory’ is set to ‘Backup the password to Azure AD only’

LAPS (Local Administrator Password Solution) is an incredibly important solution to prevent lateral movement between devices. At the high level, it is designed to automatically manage the local administrator password on each device, and make it unique. This means if someone was able to obtain the password on a single device, they can’t then use that same account against every other device in an organisation. More details: https://learn.microsoft.com/en-us/windows-server/identity/laps/laps-overview (and back in 2017 I was going on about it too https://www.adamfowlerit.com/2017/02/havent-deployed-laps-yet/)

Up until October 2023, this was only an on-premises natively supported solution; but now Intune supports it too. If you haven’t looked into LAPS or didn’t realise you could now do it in a cloud only environment, then put it at the top of your list.

Assuming you are now living with LAPS, the option Backup Directory controls where the LAPS password for each device goes. Apart from the default disabled option, this can either be ‘Backup the password to Active Directory only’ or ‘Backup the password to Azure AD only’ (yes I know it’s now Entra ID, nobody’s updated this name yet).

If you’re cloud only (Entra ID Joined) or cloud first, then this option should be ‘Backup the password to Azure AD only’ – your Entra ID should be more secure than your Active Directory, and this decision should really be a part of whatever system you’re putting first. It’s also a bit neater to view/report on events where any account is looking at the LAPS password value of a device in Entra ID, compared to on-premises Active Directory where you may have many different AD domain controllers and hopefully good monitoring/reporting of events across the entire environment – but more room for error there.

Creating a policy for this is quite a simple process from the Microsoft Intune Admin Center:

3. Ensure ‘Allow Cross Device Clipboard’ is set to ‘Block’

I am a huge fan of Clipboard in Windows and use it many times every single day. If you aren’t aware of this feature, press Winkey + V on your keyboard and it’ll pop up, asking if you want to enable it. It keeps a history of your clipboard contents – whatever you Ctrl + X or right click > copy. This is really handy when you’re copying all the time, but want to paste/recall anything beyond the absolute last thing you copied. It supports both text and pictures. Of course, this means it will copy things like passwords and other data you probably don’t want floating around. One feature of Clipboard in Windows is the ability to enable ‘Clipboard history across your devices’ which sounds somewhat handy, but drastically increases the risk of data leakage when you’re syncing that information to your account (if a work account, then should sit securely in your M365 tenant/Entra ID) or Microsoft consumer account. It’s just an unnecessary risk for little benefit – the clipboard history should stay local and be cleared on logoff/reboot. It will purely sit in memory and be lost afterwards when Clipboard sync is disabled.

Please start or keep using Clipboard in Windows but turn off Clipboard sync. It’s enabled by default.

Here’s the registry setting: Allow Clipboard synchronization across devices (admx.help)

4. Ensure ‘Notify Unsafe App’ is set to ‘Enabled’

Another setting disabled by default. Instead of explaining, I’ll just quote directly from the Group Policy setting:

This policy setting determines whether Enhanced Phishing Protection in Microsoft Defender SmartScreen warns your users if they type their work or school passwords in Notepad, Winword, or M365 Office apps like OneNote, Word, Excel, etc.

If you enable this policy setting, Enhanced Phishing Protection in Microsoft Defender SmartScreen warns your users if they store their password in text editor apps.

If you disable or don’t configure this policy setting, Enhanced Phishing Protection in Microsoft Defender SmartScreen will not warn users if they store their password in text editor apps.

This one sounds pretty reasonable right? If a user types their password into a program being monitored by Enhanced Phishing Protection, it’ll pop up and tell you:

Note that with my testing, this doesn’t apply to Microsoft Edge, nor does it apply if you paste your password, it has to be typed – but still a pretty good user reminder on something they shouldn’t be doing!

Interestingly I couldn’t find the registry value on GetADMX but the ‘Notify Unsafe App’ setting is available in Group Policy, and in Intune – create a Settings catalog policy, and use the settings listed under the category SmartScreen > Enhanced Phishing Protection: Notify Unsafe App. Further information here: https://learn.microsoft.com/en-us/windows/security/operating-system-security/virus-and-threat-protection/microsoft-defender-smartscreen/enhanced-phishing-protection?tabs=intune

Also worth calling out checking out the other Enhanced Phishing Protection settings at the same time: Automatic Data Collection, Service Enabled, Notify Malicious. Notify Password Reuse.

5. Ensure ‘Turn off toast notifications on the lock screen (User)’ is set to ‘Enabled’

This final one is pretty obvious. When a PC is locked, you don’t want notifications popping up that may contain sensitive information and be visible by anyone that can see the screen. This is a feature that I don’t think should even exist… but it does and it’s on by default. You want to enable the setting to disable the feature (yes this is a dig at the inconsistent state of settings and enabling/disabling!).

Easily done via Turn off toast notifications on the lock screen (admx.help) or enable the Turn off toast notifications on the lock screen via Intune via a Configuration Profile. A full guide is available here: Disable Toast Notifications From Lock Screen Using Intune HTMD Blog (anoopcnair.com)

That’s it for the list – as always I hope you found it interesting and love hearing any feedback (including constructive criticism), and hope it helps people out there to always be thinking security.

5 Things To Check In Your Microsoft 365 Tenant

Posted on by Adam Fowler

I’ve been diving into the Center for Internet Security’s (CIS) benchmarks lately – which are a set of benchmarks to use against different technologies (including Microsoft 365 and freely available for non-commercial use). They are a good set of checks to go through in a tenant to review configuration with a security focus; including how to remediate.

There is of course a lot more to it than reading a document and configuring items the way it says to; you need to understand what you’re changing, and what impact that may have to the business and it’s end users. For example; blocking the ability to share anonymous links from SharePoint/OneDrive is generally ‘a good idea’ security wise, but if your users are actually doing that you probably don’t want to just shut that off. You need to assess what’s being used and how, and have a strategy to get to a more secure point.

Anyway, I’ve picked my favourite 5 settings from their comprehensive list that I feel people could miss; I may have missed these myself when I used to be a Microsoft 365 administrator.

For PowerShell commands, if you’re not sure how to get to the right module (e.g. Exchange Online from my first example) then check out msshells.net which will show you how to install and connect.

The headings are quoted from CIS, but the rest of the material is my own:

1 – 3.1.1 Ensure Microsoft 365 audit log search is Enabled
If you’re a Microsoft 365 focused admin, Azure and log search may not be a front of mind for you unless you go looking to solve a problem that arises.

This should be enabled in new tenants, but older ones may not have it. First check it’s status with the PowerShell command in Exchange Online:

Get-AdminAuditLogConfig | Select UnifiedAuditLogIngestionEnabled

This will show a True or Fasle value – if it’s True, it’s on. If it’s off/false, enable it with this command:

Set-AdminAuditLogConfig -UnifiedAuditLogIngestionEnabled $true

This should have no user impact and just enables the ingestion of the Audit Logs.

To view these logs you can use PowerShell commands, but this is generally one I’d rather use a GUI for – go to the Microsoft Purview portal and the Audit section, and trigger a search. Without getting into too much detail, there’s two tiers of Audit – Standard and Premium. Read further information here.

2. Ensure modern authentication for SharePoint applications is required

This is another that many old tenants may have disabled. SharePoint has ‘legacy authentication’ similar to other services that are planning or already deprecated legacy auth – Exchange Online being the common one most people know about.

To check if you have this disabled, connect via PowerShell to SharePoint Online and run the command:

Get-SPOTenant | ft LegacyAuthProtocolsEnabled

True means it’s enabled, False means disabled – and we want it to be False. The command to enable it is:

Set-SPOTenant -LegacyAuthProtocolsEnabled $false

Entra ID’s Conditional Access should be configured to block all Legacy Auth requests also, but this is an extra layer to make sure SharePoint won’t work that way anyway (plus holes are poked through Conditional Access all the time!). There seems to be very little official public documentation about this option from Microsoft – I could find this example where they show how to set it to $true to avoid some login issues which is a bit concerning.

This is one that may have some user impact or application impact if systems are connecting to SharePoint Online in legacy ways. Users should be used to modern auth and match their experiences in other Microsoft 365 services – applications however would need to be redesigned or updated to accommodate this. You can search the Entra ID authentication logs for any attempts to connect to SharePoint Online using legacy authentication over as long as possible before changing this setting.

3. Ensure sign-in to shared mailboxes is blocked (Automated)

Shared Mailboxes are both a delight for having a central area for emails to go to, and multiple staff having access to them, but also a dismay in user expectations of being able to send as the account, and potentially log in as it. A reception desk or similar may have multiple people jumping in and out of the location, but they want to access the same contents without the time-taking task of logging in and out of the computer each time. Regardless – security wise each user should have a unique login, and all their actions performed under that login.

Although it can be a fight and go way beyond a technical issue – shared mailboxes should be disabled from logging in. A disabled from login shared mailbox can still send and receive emails; you’re only disabling the ability to log in using that account itself, and the mailbox can still be accessed as a delegate.

As this is a per account setting, you’ll need to check all shared mailboxes. As per Microsoft Learn, you can block a single account from the Microsoft 365 Admin Center and go to Users > Active Users, select a Shared Mailbox, and click the ‘Block Sign-In’ option:

… but this doesn’t really scale to check all Shared Mailboxes and change the setting. Instead, as per Microsoft Learn, we have to use Exchange Online PowerShell to find the shared mailboxes, then we can use Microsoft Graph PowerShell SDK to disable them. After connecting to Exchange Online and Microsoft Graph with the below scope:

Connect-Graph -Scopes User.ReadWrite.All

You can then run the one command to use Exchange Online to find all Shared mailboxes and then use Microsoft Graph to set the account to disabled:

Get-EXOMailbox -RecipientTypeDetails "SharedMailbox" | ForEach {Update-MgUser -UserId $_.ExternalDirectoryObjectId -AccountEnabled:$false}

You could also do the same for Room and Equipment mailboxes if they don’t need to sign in:

Get-EXOMailbox -RecipientTypeDetails "RoomMailbox","EquipmentMailbox" | ForEach {Update-MgUser -UserId $_.ExternalDirectoryObjectId -AccountEnabled:$false}

Also note that Exchange Online has it’s own ‘AccountDisabled’ variable which you could set to true, but this blocks sign in to the mailbox, and not the entire account to any M365 service/Entra ID authentication.

User impact on this needs to be assessed by again checking the Entra ID logs against each Shared Mailbox, and working out how to set systems up to avoid the shared account login. There may be some user resistance to this, but one argument could be ‘what if someone sent a nasty email to your boss under the account and they thought it was you – you couldn’t prove it wasn’t easily if others are also using that same account’.

4. Ensure ‘Per-user MFA’ is disabled

This is the ‘old’ MFA before Conditional Access was around. This only suported the MFA methods of ‘Call to phone, Text message to phone, Notification through mobile app, and Verification code deom mobile app or hardware token’.

You can check if any users have this enabled by going to https://account.activedirectory.windowsazure.com/usermanagement/multifactorverification.aspx and ensuring all users show as ‘disabled’ for the ‘MULTI-FACTOR AUTHENTICATION STATUS’ column.

If you see any users enabled, then you should ensure Conditional Access is set up and ready to go, then change the users to disabled. You also shouldn’t be using this function at all when Conditional Access is enabled. A few warnings from Microsoft:

More details here: https://learn.microsoft.com/en-us/entra/identity/authentication/howto-mfa-userstates

5. Ensure a dynamic group for guest users is created

I quite like this one. Yes, you can reasonably easily determine if an account is a guest account or not, but having an automated group means it’s easy to point other Conditional Access policies, or other monitoring, on what these accounts are doing in your tenant. It’s very little effort to create, doesn’t need maintenance, and can help in other scenarios when you want to review what guest accounts are around.

How to do this is well documented by Microsoft but you do need an Entra ID Plan 1 or Plan 2 license to create dynamic groups.

Simply create a New Group in the Entra Admin Center https://entra.microsoft.com/#view/Microsoft_AAD_IAM/AddGroupBlade

and after selecting a Group Name and choosing Memebership type: Dynamics user, click ‘add dynamic query’:

Use the filters Property = userType, Operator = Equals, Value = Guest, and click ‘Save’, then ‘Create’.

Note that it can take a minute for the group to initially populate. You can now use this group to block from certain things as an extra layer of protection against accidental permissions, or have extra Conditional Access policies that always require certain MFA methods.

If you don’t have Entra ID Plan 2 to be able to have guest reviews, you could use the membership of this group as a simple way to review the guest accounts in your tenant.

That’s my top 5 picks – check out the CIS Benchmark for Microsoft 365 yourself along with their other benchmarks as there’s a lot to learn and check through. It’s also not a one-time thing, settings change, the benchmark itself grows (currently at v3.1 at the time of writing), plus there’s more security to check beyond this!

Microsoft Copilot for Microsoft 365 Enablement Experience

Posted on by Adam Fowler

I’ve recently purchased Copilot for Microsoft 365 to play with on my own tenant, and wanted to share my experience. No, I did not use Copilot or any other AI to write this post :) Some of the below may sound picky, but I’m trying to be clear around names and functions as I found a lot of it hard to correctly define as I went. You’re going to see the word ‘Copilot’ a lot – sorry.

First, I’ll attempt to clarify that I’m only looking at Copilot for Microsoft 365. What is “Microsoft Copilot” is a harder question to get your head around, because Bing Chat for Enterprise/Bing Chat Enterprise is now just called Copilot. Copilot for Microsoft 365 is Copilot integrated into the Microsoft 365 apps – so think of Copilot as the AI solution itself, and “Copilot for X ” as anything else as Copilot being integrated with, and able to use some of the data in it, as well as giving answers more contextual to that solution (but not limited to!).

I found this really good graphic of Microsoft Copilot but can’t find the original source!


Alright, so looking at the options below we have Copilot which is free, Copilot for Microsoft 365 which you pay for per user and integrates into Microsoft 365 apps… and there’s also Copilot Pro which gives you integration with some of the Microsoft 365 apps and a few extra base Copilot perks. Copilot Pro is for consumers and targeted at individuals, you can’t buy this against a business account.

In my own tenant of 1 active user, I purchased Copilot for Microsoft 365. I had to do this for a year because it was either that, or 3 years. My tenant is quite old, US based, and also has some trial/unique test licenses applied from Microsoft.

Just for reference too, Copilot for Microsoft 365 data and processing stays within the service boundary, and is not read or used by Microsoft in any other way.

Source: https://learn.microsoft.com/en-us/microsoft-365-copilot/extensibility/ecosystem

Note that despite the official diagram above’s title is “Microsoft 365 Copilot”, that was the name at launch and it is now “Microsoft Copilot for Microsoft 365”

The purchasing and assigning of Copilot for Microsoft 365 is somewhat of a non-event like most other licenses. I was able to buy a single license, as Microsoft reduced the 300 minimum requirement in December 2023. From the Microsoft 365 admin center, you have the following subservices available:

From the user side, I just noticed the Copilot options turn up as soon as I went to check them. The first thing I wanted to work out, was how do I interface with Copilot when it’s app agnostic? Here’s where the fun started;

https://copilot.microsoft.com, https://www.microsoft365.com/chat/, and https://bing.com/chat look pretty much the same, two have a ‘work’ option to make sure you’re processing data in your own tenant and not giving sensitive information back to Microsoft in other ways… and the third requires a work login to access – so what’s the difference?

Honestly I’m not sure. I tried working this out but failed – maybe there isn’t one? It will save what you searched, and that history will be visible across all three chat solutions:

I was going to use this example question of ‘how many emails did I get yesterday’ as my next point of frustration – when I have been testing this for the last few days, it’s incorrectly told me each time that I’ve received just 1 email. Then when asking it about another email I received in that yesterday timeframe, agreeing that also was received yesterday. When questioning it around the discrepancy, it stopped the conversation.

However, it looks like that’s already been resolved:

I am glad it’s now not giving an incorrect answer, but I did expect it to be able to actually answer this question with a correct number. We’ll move on to finding some information I know is in there:

I asked to see ALL the emails where I’ve passed a Microsoft exam. It found one from 2008, something else irrelevant to exams, and then 6 other emails for me to check out.

Note that I have a bunch of emails that should quite clearly be picked up, such as this one from February this year and I found by doing a search of the word ‘Exam’ on my mailbox:

How about certifications then? For some reason it did find a much newer email about a Certification renewal (the word ‘Exam’ wasn’t on that one). When I asked to ‘show me more emails’ it proceeded to just do what I asked out of context, and showed me 5 example emails from my mailbox unrelated to the previous query.

These experiences are frustrating – partly because I can see the amazing potential Copilot has (honestly I can!), but also how it can consistently miss the mark of my expectations around it. It could be that my expectations are too high – but if they are, then it’s Copilot’s job to set them correctly as part of it’s answer system. And no, putting a label saying ‘AI-generated content may be incorrect’ at the bottom of everything doesn’t quite cut it.

OK, how about asking Copilot for Microsoft 365 about files? Asking it what I accessed last is correct, and matches what I see on the ‘My content > All’ section of Microsoft 365. However, that fell over quickly when I asked it was folders were in the root of my OneDrive – it claimed it’d have to do a search for that (why don’t you just go search then?), as well as showing me an ini file I’d opened 6 days ago for Diablo IV – and for reference, that was the 7th last file I’d accessed. Asking it to search for the folders resulted in it telling me that now it had done that search but couldn’t list the folders. Taking it’s next suggestion, I asked it to list the contents of a folder called Work – I’d created it a few days ago and it has only ever had 1 file in it. The results came back incorrect again, claiming the presentation2 file which as per the first result, was in a folder called ‘Documents’ and not in a folder called ‘Work’.

OK, enough digging for data.

My other surprise on purchasing the Copilot for Microsoft 365 license was receiving a call at about 5am, which although I woke up to, did not answer in time. I called it back, heard a recording saying it was Microsoft, and assumed it was a scam call. Checking my emails later, I noticed that a case had been logged in my name at 1:06am called “Getting started with Copilot, we’re here to help.”

I logged onto the support area of the Microsoft 365 Admin portal, and yes there was a ticket under my name, with my mobile phone number (including the +61 area code for Australia) that had been logged for me. Yes, I have notes on this experience:

  1. Although Microsoft Support can be used for both break/fix and advisory calls, it should not be used as a marketing tool to proactively ensure a customer is getting value from something they only just purchased. In other words, don’t shoehorn a solution to a problem you see, into a different system not designed for that.
  2. Don’t list it as the customer doing the action themselves if you automate something on their behalf.
  3. Don’t put down on my behalf that I’d like a phone call about the ticket you logged pretending to be me.
  4. Have a look at the customer’s timezone and call them during business hours.
  5. Who came up with the incident title? At least start with ‘Auto generated’ – you’ve used the title as a way to communicate to me when that’s very much not what the title of an incident is supposed to do.
  6. After calling me and waking me up, don’t send an email asking me to respond, but if I don’t you’ll call back again, but claim to do so ‘again’ during business hours.
  7. Don’t use the Status of ‘Feedback’ when it really isn’t – I’m probably not going to have feedback a few hours after enabling the service (but give me a few days to write up a blog post!).

Support also advised me that “A ticket is logged when copilot is purchased” and proceeded to give me a bunch of links about Copilot for Microsoft 365 anyway. Seems like that could have just been the email they sent without all the other noise.

There was one good link in there which was about Copilot prompts – worth a quick look but seriously, why isn’t this just linked at the top of the Copilot prompt area? There’s a lot of white space this link could go in.

I’ve had a few others claim similar experiences when enabling Copilot for Microsoft 365 including Microsoft MVP Karen Lopez:

Yikes.

I know I’ve banged on about frustrations here, but my general point is to try and set realistic expectations around the current state of Copilot for Microsoft 365. It is not a magical answer to doing most your work for you. It is really good at writing responses for you as either starters, frameworks, or mostly done content to fine tune. It’s really good at summarising emails. It’s really good at responding to something you don’t want to spend time on – I was ‘invited’ to attend free LinkedIn Workshops to help me put content on that platform, and clicking reply brings up a great Copilot experience – auto answer type buttons depending on the response I want to give, an area to get Copilot to help me draft a response, or I can just start typing and Copilot stays out of the way.

Although I can’t think of many situations that a poem would be my response, it’s one of those options you have to try:

So yes, these sorts of functions are hugely valuable just for these sort of use cases on email. It also does a lot of great stuff in Word, PowerPoint, and Excel, along with Outlook as above – but those deserve their own posts. Copilot, and in turn Copilot for Microsoft 365 is going to get better at a hugely accelerated rate, and the items that are less focused on purely the language side of LLM and a bit more data based will be valuable. And, despite my criticisms above, I still think everyone should buy or at least try this to learn, get ready, and understand what is actually possible right now in our era of AI – just make sure your environment is ready for it with the right controls, processes, and security in place.