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1Scan for outdated or missing drivers - takes under a minute2Clear out junk files and repair common Windows errors3Fix the driver behind crashes, sound loss and screen glitchesTo connect on-premises Active Directory Domain Services (AD DS) to Microsoft 365, synchronize selected identities to the Microsoft Entra ID tenant associated with your Microsoft 365 organization. Microsoft offers two approaches: Microsoft Entra Connect Sync, installed on a server, and Microsoft Entra Cloud Sync, which uses provisioning agents. Prepare and secure the directory and sync infrastructure before enabling exports, then validate the objects and functions your organization relies on.
What directory synchronization does
AD DS is the on-premises source directory; Microsoft Entra ID is the cloud directory used by a Microsoft 365 tenant. Synchronization copies and maintains selected identity information—such as users, groups, contacts, and configured attributes—between them. Administrators define which objects and attributes are in scope.
Microsoft Entra Connect Sync runs its synchronization engine on an installed server. Microsoft Entra Cloud Sync uses provisioning agents on domain-joined servers. Both support core user, group, and contact synchronization, but their supported features and operating models differ. Older environments and documentation may still call Microsoft Entra ID “Azure AD” and Microsoft 365 “Office 365.”
Prepare AD DS before the first sync
Start by deciding which forests, domains, organizational units (OUs), objects, and attributes should be synchronized. Clean up the identities that will be used with Microsoft 365 before connecting them: incorrect or conflicting directory values can cause synchronization errors or warnings, and fixes may take additional sync cycles to appear.
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- Check that user principal names (UPNs) are valid and unique where possible. Microsoft recommends aligning AD DS UPNs with the corresponding Microsoft Entra UPNs for the best synchronization experience.
- Review email and proxy address values for validity and uniqueness. Resolve duplicate proxy addresses rather than choosing a value automatically when the conflict needs a business decision.
- Confirm that display names and contact details are accurate if they should appear in the global address list.
- Use Microsoft’s IdFix utility to find formatting and duplicate-value issues. Review each finding and determine the correct business value before making changes; the tool does not decide which conflicting record is authoritative.
Take an inventory of the intended scope before configuration. A documented object and attribute scope makes it easier to review the synchronization result and to keep a later migration from assigning the same identity to two synchronization tools.
Choose Connect Sync or Cloud Sync against your requirements
Neither option is universally better. Compare the requirements of your topology and Microsoft 365 workloads with Microsoft’s current feature comparison before committing: supported features, limits, and prerequisites can change.
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| Consideration | Microsoft Entra Connect Sync | Microsoft Entra Cloud Sync |
|---|---|---|
| Operating model | Installed synchronization engine on a server. | Cloud-oriented provisioning with agents on domain-joined servers. |
| Capabilities identified in Microsoft’s comparison | Supports device synchronization. | Supports disconnected-forest scenarios and multiple active agents. |
| Other requirements to verify | Check the current comparison for scale and group-size limits, writeback features, custom rules, authentication configuration, topology support, and migration eligibility. Support differs by capability and configuration. | |
Choose based on actual dependencies
Before choosing, establish whether you need device synchronization or hybrid join, custom synchronization rules, disconnected forests, particular password or group writeback capabilities, large-group support, or a complex forest and domain topology. Confirm requirements for pass-through authentication or federation as well. Do not infer that a feature is supported merely because both products synchronize basic users and groups.
Microsoft says its development focus for new provisioning capabilities centers on Cloud Sync, but its migration guidance also recognizes that organizations may need to stay on Connect Sync when a required feature is not supported in Cloud Sync. Use the live comparison and migration guidance for the specific configuration you operate.
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How to synchronize domain users to Microsoft 365
Use a controlled rollout rather than enabling broad production scope as the first test. The sequence below applies to either approach; the server and agent setup details differ, so follow the current product-specific prerequisites and configuration guidance.
- Define the scope. Record the forests, domains, OUs, users, groups, contacts, and attributes that should be synchronized. Identify representative accounts and groups for validation.
- Correct directory data. Resolve the UPN, proxy address, and profile-data issues found during preparation. Confirm which values are intended to be authoritative when records conflict.
- Confirm prerequisites and provision the host. Microsoft’s current Connect Sync prerequisite guidance recommends Windows Server 2025 or Windows Server 2022 and requires a writable domain controller. Cloud Sync also requires a domain-joined host. Check Microsoft’s live prerequisite pages for supported server and agent versions before installation because requirements can change.
- Set up the selected synchronization approach. For Cloud Sync, setup requires a Hybrid Identity Administrator account and appropriate Active Directory administrator credentials. Microsoft recommends three active agents for high availability. For Connect Sync, configure the server and synchronization scope according to the current deployment guidance.
- Review the resulting scope and changes. Check which objects and attributes are selected, then validate the result for representative users, groups, and contacts. Where using Connect Sync, staging mode can process and retain pending changes for review without exporting them to Microsoft Entra ID.
- Activate exports deliberately. Enable production export only after validating the scope and pending changes. Maintain one active Connect Sync export path; do not activate a second server while the first remains active.
- Monitor and verify business outcomes. Check individual identities, group membership, required attributes, and any configured writeback or hybrid functions. Aggregate object counts alone do not establish that the identities your organization depends on are correct.
Secure the synchronization infrastructure
A synchronization server or agent host is privileged identity infrastructure, not an ordinary utility server. Microsoft recommends treating Connect Sync as a Tier 0/control-plane asset. Someone who controls the synchronization infrastructure may be able to affect cloud identities, so restrict who can administer it and use dedicated privileged accounts.
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- Limit server and agent administration to authorized identity administrators; avoid routine use of privileged accounts for unrelated work.
- Coordinate DNS and connectivity to configured domains and Microsoft endpoints with identity and infrastructure teams. Account for firewall, proxy, TLS, and server-hardening requirements.
- Include the host, its administrative access, and its configuration in the organization’s privileged-infrastructure protections and operational monitoring.
Use staging mode and manage cutovers safely
What Connect Sync staging mode does
A Connect Sync server in staging mode runs import and synchronization processing but does not export pending changes to Microsoft Entra ID. The changes remain available in its Connector Space for review. This makes staging useful for configuration testing, previewing results, and preparing a failover server. Microsoft recommends keeping a staging server synchronized so it can take over without a large catch-up cycle.
Keep one active Connect Sync export path
Only one Connect Sync server should be active at a time. Before switching roles, confirm the intended server’s staging state and review pending exports. Microsoft warns that activating one server while another remains active can disrupt password writeback. Do not treat staging as permission for two servers to export concurrently.
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Move from Connect Sync to Cloud Sync
Connect Sync and Cloud Sync must not manage the same objects side by side. Microsoft’s migration guidance calls for separating scope—such as with OUs—so each object is managed by only one tool at a time. Pilot or validate the change, back up the Connect Sync configuration, and check which configuration elements are eligible to migrate. Migration options depend on the tenant’s state and the configuration in use.
Before retiring the former sync path, verify representative objects and attributes, group memberships, writeback behavior where configured, and any required hybrid functions. Keep rollback and cutover responsibilities clear so a scope change does not leave identities unmanaged or create overlapping exports.
Understand what depends on synchronization
Directory sync can underpin capabilities beyond creating cloud user records. Microsoft identifies seamless single sign-on and Exchange hybrid scenarios among its related use cases; Exchange hybrid can include a shared global address list and mailbox coexistence. These are workload-specific dependencies, not automatic benefits of turning on basic synchronization.
The default export pattern is cloud-directed, while writeback is a separate, supported configuration that sends selected information back to AD DS. Identify which writeback features and hybrid functions are actually configured before changing scope, moving tools, or removing synchronization. A change that preserves user objects may still affect a dependent sign-in or Exchange scenario.
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