Troubleshooting Microsoft Entra ID to Microsoft Entra ID Device Migrations

Overview

The general troubleshooting flow

Step 1 — Review the Cloudiway migration logs

Before performing any troubleshooting on the device, review the migration logs in the Cloudiway portal. Identify the last successful operation and determine whether the migration failed:

The logs provide important information about what Cloudiway was attempting to perform when the migration stopped.

Once you have identified the migration phase, follow the appropriate section below.

Scenario 1 — Migration failed after the first reboot

If the migration fails after the first reboot, the device may still be connected to the source tenant, or may have been disconnected from the source tenant without successfully completing the next migration phase.

Step 1 — Log in with the Cloudiway local administrator account

Attempt to log in to the affected device using the local administrator account created by the Cloudiway Migration Agent. This account is created during the migration process to provide administrative access to the device if the source or target user's credentials cannot be used.

Once logged in, verify the current Microsoft Entra ID registration status of the device.

Step 2 — Check the current tenant connection

Open Command Prompt as Administrator and run:

dsregcmd /status

Review the output, particularly the Device State section. For a Microsoft Entra ID joined device, you would normally expect to see information such as:

AzureAdJoined : YES

Also review the tenant information to determine whether the device is currently associated with the source tenant or the target tenant. Based on the result, proceed with the appropriate scenario below.

Scenario 1A — Device is still connected to the source tenant

If the device is still correctly connected to the source Microsoft Entra ID tenant, the migration can generally be attempted again. Perform the following steps:

Scenario 1B — Device is not connected to either tenant

If dsregcmd /status or the Windows account configuration shows that the device is no longer connected to either the source or target Microsoft Entra ID tenant, the device should first be returned to a valid source state. Perform the following steps:

Scenario 2 — Migration failed after the second reboot

A different troubleshooting approach should be followed when the migration fails after the second reboot, particularly when the user cannot log in using either:

• •The source user's credentials, or
• •The target user's credentials.

At this stage, it is important to determine whether the device was successfully added to the target tenant during the migration.

Step 1 — Check the target Microsoft Entra ID audit logs

Sign in to the target Microsoft Entra admin center and review the device audit logs. Navigate to:

Search for events related to the affected device around the time the migration was performed. Look for events indicating that the device was:

The objective is to determine whether Cloudiway successfully added the device to the target tenant before the failure occurred.

Scenario 2A — Device was never added to the target tenant

If there is no indication in the target Microsoft Entra ID logs that the device was successfully added, review the Cloudiway migration logs for the registration/join failure. Potential areas to investigate include:

Scenario 2B — Device was added and subsequently removed

If the Microsoft Entra ID audit logs confirm that the device was successfully added to the target tenant but was later deleted or removed, this indicates that the target registration initially succeeded.

In this situation, investigate the target Microsoft environment to determine what caused the device to be removed. Review configurations such as:

The Microsoft Entra ID audit logs should be used to identify the operation and, where available, the service or account responsible for removing the device.

Recover the device after identifying the root cause

Once the underlying issue has been identified and corrected, attempt to access the affected device using the Cloudiway local administrator account.

If the device is currently disconnected from both tenants and the migration had already progressed to the target registration phase, you may need to manually connect the device to the target Microsoft Entra ID tenant.

After connecting the device

Troubleshooting decision tree

Use the following flow to quickly determine the appropriate troubleshooting procedure.

Migration failed
  ↓
Check Cloudiway migration logs
  ↓
Failed after the FIRST reboot?
  → Log in using the Cloudiway local administrator account
  → Run dsregcmd /status
  → Determine the current tenant connection
     │
     ├─ Device still connected to source
     │    → Verify source connection
     │    → Re-run Cloudiway Migration Agent
     │    → Restart migration
     │
     └─ Device connected to neither tenant
          → Log in using Cloudiway local administrator
          → Reconnect device to source tenant
          → Verify source registration
          → Re-run Cloudiway Migration Agent
          → Restart migration

Failed after the SECOND reboot?
  → Review target Microsoft Entra ID Audit Logs
     │
     ├─ Device was never added to target
     │    → Review Cloudiway logs
     │    → Check authentication/account configuration
     │    → Check enrollment restrictions and target tenant policies
     │    → Correct the underlying issue before retrying
     │
     └─ Device was added and later removed
          → Cloudiway successfully completed the target join operation
          → Review Microsoft Entra ID/Intune logs and policies
          → Determine why the device was removed
          → Correct the target tenant configuration
          → Log in using the Cloudiway local administrator account
          → Manually connect the device to the target tenant if required

Information to collect before contacting Cloudiway Support

If the issue persists after performing the above troubleshooting, collect the following information before opening or updating a Cloudiway Support ticket:

Providing this information will help the Support team identify the migration state and determine the appropriate next troubleshooting steps.

Important considerations

References

For additional information, refer to the following Cloudiway Help Center articles:

• • Azure AD to Azure AD Tenant Migration
• • Troubleshooting Device Migrations