Microsoft Entra Connect Sync Is Being Retired — What Every IT Admin Needs to Know (2026)

If you are an IT admin managing a hybrid Microsoft environment, 2026 is the year you cannot afford to look away from Microsoft Entra ID. Microsoft is actively retiring on-premises identity tooling, enforcing new security baselines, and pushing organizations firmly toward cloud-native identity management. This post is the first in a series covering everything you need to know — starting with the biggest infrastructure change: the end of Microsoft Entra Connect Sync. 

Microsoft is transitioning from Microsoft Entra Connect Sync to the cloud-native Entra Cloud Sync to simplify hybrid identity management and strengthen Zero Trust security, reducing on-premises complexity while improving reliability, security, and day-to-day operations. This is arguably the most impactful change for enterprise IT admins — if you're still running Connect Sync, your migration window notification will arrive via M365 Message Center starting July 2026. Microsoft Community Hub

Upcoming Change - Migrate from Microsoft Entra Connect Sync to Microsoft Entra Cloud Sync

Type: Plan for change
Service category: Entra Connect
Product capability: Entra Connect

As organizations look to strengthen identity security and advance their Zero Trust strategies, many are looking for simpler, more reliable ways to manage hybrid identity. To support these needs, we’re beginning the transition from Microsoft Entra Connect Sync to the cloud‑native Microsoft Entra Cloud Sync - helping reduce on‑premises complexity while improving security, reliability, and day‑to‑day manageability.

This shift is a key step toward a cloud-managed identity future that will provide a more secure, resilient, and easier-to-operate synchronization experience. As part of ongoing modernization efforts, Microsoft’s strategy remains to deliver stronger security, improved reliability, and simpler identity operations.

What's next

Beginning in July 2026, we will begin notifying customers through the M365 Message Center, Entra Connect Health, and targeted emails about their individual transition timelines. The transition will be rolled out in phases, and we will reach out directly to each organization when their assigned transition window begins. This phased approach ensures that we can provide tailored guidance and support to all our customers.

• Initial phases: In the first waves, we will focus on tenants for whom Entra Cloud Sync already meets all their identity synchronization needs. If your organization relies on advanced features or has a large directory, you will not be among the initial targeted groups. We will prioritize early transitions for customers with straightforward configurations that are fully supported by Entra Cloud Sync’s current capabilities.

• Subsequent phases: As Entra Cloud Sync’s capabilities expand, we will progressively notify the later groups and ensure they can transition successfully once equivalent support is available in Entra Cloud Sync

We are committed to supporting you by providing tooling and documentation for the transition to Entra Cloud Sync.

What's changing

Once your organization is notified of its assigned transition window, you will receive detailed guidance and resources to help you begin the move to Entra Cloud Sync. During this period:

• You will need to review your current configuration, assess readiness, and familiarize yourself with Cloud Sync’s capabilities.

• You will gain access to the transition tool and step-by-step documentation to support a smooth transition.

• You will move and test your synchronization environment in Entra Cloud Sync before any permanent changes are made.

Once your transition to Entra Cloud Sync is successfully completed:

• Entra Cloud Sync will be the primary mechanism for identity synchronization capabilities between Active Directory and Entra ID, replacing the identity sync functionality in Entra Connect tool.

What's not changing

Once you migrate to Cloud Sync, your hybrid authentication features that enable on‑premises credentials to be used for accessing cloud resources will continue to be available after migration on the Connect Sync config wizard.

What should you do right now?

If your organisation is still running Microsoft Entra Connect Sync, here are the three immediate actions to take before your migration window arrives:

1. Assess Cloud Sync readiness — Run the Microsoft readiness assessment tool to check if your current configuration is supported by Entra Cloud Sync. Organisations with advanced features or large directories will not be in the first migration wave, but it is never too early to know your gap.
2. Watch your M365 Message Center — Starting July 2026, Microsoft will notify each organisation individually with their assigned transition window. Make sure your admin notification email is current and someone is monitoring the Message Center actively.
3. Upgrade Entra Connect now — Even before your migration window, upgrade to the latest version of Microsoft Entra Connect and disable hard-match takeover. This protects against SyncJacking attacks independently of when you migrate.

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This is Part 1 of a series on Microsoft Entra ID changes in 2026. Coming next: SyncJacking — what it is, how the attack works, and how to fully harden your hybrid environment against it.

Found this useful? Leave a comment below— I read every one. You can also follow this blog for more Microsoft identity and infrastructure deep-dives from a practising IT admin with 15 years in the field.

Choosing an Office 365 User Authentication Method

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Choosing an Office 365 User Authentication Method

Authentication

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With the exception of internet sites for anonymous access created with SharePoint Online, users must be authenticated when accessing Office 365 services.

·         Modern authentication Modern authentication brings Active Directory Authentication Library (ADAL)-based sign-in to Office client apps across platforms. This enables sign-in features such as Multi-Factor Authentication (MFA), SAML-based third-party identity providers with Office client applications, and smart card and certificate-based authentication. It also removes the need for Microsoft Outlook to use the basic authentication protocol. For more information, including the availability of modern authentication across Office applications, see How modern authentication works for Office 2013 and Office 2016 client appsand Using Office 365 modern authentication with Office clients.

Modern authentication is not turned by default for Exchange Online. To learn how to turn it on, see Enable Exchange Online for modern authentication.

·         Cloud identity authentication   Users with cloud identities are authenticated using traditional challenge/response. The web browser is redirected to the Office 365 sign-in service, where you type the user name and password for your work or school account. The sign-in service authenticates your credentials and generates a service token, which the web browser posts to the requested service and logs you in.

·         Federated identity authenticationUsers with federated identities are authenticated using Active Directory Federation Services (AD FS) 2.0 or other Security Token Services. The web browser is redirected to the Office 365 sign-in service, where you type your corporate ID in the form a user principal name (UPN; for example,isabel@contoso.com). The sign-in service determines that you are part of a federated domain and offers to redirect you to the on-premises Federation Server for authentication. If you are logged on to the desktop (domain joined), you are authenticated (using Kerberos or NTLMv2) and the on-premises Security Token Service generates a logon token, which the web browser posts to the Office 365 sign-in service. Using the logon token, the sign-in service generates a service token that the web browser posts to the requested service and logs you in. For a list of available Security Token Services available, see Single sign-on roadmap.

Office 365 uses forms-based authentication, and authentication traffic over the network is always encrypted with TLS/SSL using port 443. Authentication traffic uses a negligible percentage of bandwidth for Office 365 services.

As an Office 365 admin, you might feel the only way to manage users (on occasions!) is with the whip. Unfortunately, that’s not allowed anymore, so you’ll have to get a bit more sophisticated with your management skills.

When users want to access Office 365, they have to be authenticated. Users in your organization will already have a username and password, most likely while using an internal Active Directory. Of course, you could create separate Office 365 user accounts for your users, but ideally you would make them “reuse” existing on-premises accounts.

I’ve put “reuse” deliberately between quotation marks, as technically speaking this is not entirely true for all possible scenarios. More about that later.

User management is very important. You don’t want the wrong users to have access to the wrong resources, or even worse, have hackers gain access to internal data by hacking user accounts. So, think carefully about authentication and authorization options when using Office 365.

Single Sign-On with Your Existing Active Directory

As mentioned above, you can make use of your existing authentication system (like Active Directory) when implementing authentication for Office 365. Before I explain the possible options, you must know that behind the scenes Office 365 uses Azure AD for authentication. Every Office 365 tenant has a separate Azure AD.

There are two possible options:

1. Synchronized identities: Accounts are synchronized between Azure AD and your On-Premises directory. You can choose to sync passwords as well, or let users have a different password for both.
2. Federated identities: In this model, users always authenticate against your internal directory. When signing into Office 365, users are redirected to your internally hosted identity provider, like ADFS. When signed in successfully, users are redirected to Office 365 and are logged in.

Option 2 is the preferred option and is the only option that allows for a seamless, single sign-on experience. However, Option 2 also requires additional on-premises configuration for the identity provider and is therefore the more complicated option.

Option 1 is the easiest solution to set up. In most cases, organizations begin with Option 1, and eventually move to Option 2.

Multifactor Authentication

Besides the two authentication options for identity management, the third way to manage your users is multifactor authentication.

The idea behind multifactor authentication is that a physical item is required when signing in. In most cases this will be a code sent via text or phone call, or is generated by a mobile app. When logging in with your username and password, a key generated by the multifactor device must also be entered.

In the scenario in which a hacker gains the username and password, they still cannot log in unless they have access to the user’s phone. It’s not impossible, but it makes it much harder for hackers to gain access to a user’s account.

In Office 365, you can configure multi-factoraythentication from the Office 365 Admin Center. You can choose which users you want to enable it for, and what to do if the client does not allow multifactor authentication. For example, non-browser clients like Outlook don’t support multifactor authentication yet, but by configuring a so-called app password, users can still use the application.

Office 365 multifactor authentication is based on Azure AD as explained before, and therefore also uses Azure multi-factor authentication.

When it comes to managing your Office 365 users, you have three options:

1. Synchronized Identities: User accounts are synchronized between your internal directory and Azure Active Directory. Users have to login twice: once to your internal systems, and secondly to Office 365. Passwords can be synchronized between the two, so users don’t have to remember two separate passwords.
2. Federated identities: There is only one user account, which in most cases will be your On-Premises directory account. When logging into Office 365, your identity provider (e.g. ADFS) will be used to authenticate a user. Single sign-on can be implemented such that users have to log-in only once.
3. Multifactor authentication: After logging in successfully to Office 365, multifactor authentication requires them to enter a challenge response sent to them via text, a phone call, or generated by a mobile app. Only after entering the code, they can log into Office 365.

There is a fourth option I mentioned briefly earlier - namely, using separate Office 365 accounts, (so-called “onmicrosoft”-accounts, as the format isusername@tenant.onmicrosoft.com. This is only useful in demo purposes, or when you don’t have an internal directory, which is unlikely.

What Should YOU Choose?

As discussed, federated identities are, in most cases, the best solution, but it requires more configuration. When you initially sign up for Office 365, you may not want to do all of that right away. Beginning with synchronized identities and moving to federated identities at a future stage is a very solid approach.

Finally, multifactor authentication is a good thing, but requires users to enter a code every time they log in. You may want to restrict this to admins only however, in order to have the best balance between usability and security. Office 365 has awesome features like document management, version control, workflows, team sites, email, Lync, and more. However, if nobody uses it because of overly strict or overly complicated authentication requirements, it is useless.