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Thank you for taking the time to share such a detailed investigation.
Based on everything you have tested, I agree that disabling Automatic Reconnection would only avoid the path that triggers the problem. It would not explain why the affected session on Server 2025 does not recover afterward, so I would not consider that a resolution to the behavior you are investigating.
The important distinction in your findings is that the RDP connection itself appears able to reconnect to the existing session, while the Windows logon/session state does not complete the corresponding transition.
The sequence you captured is particularly useful:
- An Automatic Reconnection attempt begins and is interrupted.
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Winlogonsubsequently records event 4008. - Local Session Manager can report that the session reconnection succeeded.
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Winlogondoes not subsequently reach the normal unlock sequence you observe during a successful reconnect. - Further external RDP connections reach Please wait, although the user's applications remain running in the existing session.
The fact that Task Manager > Users > Connect can attach an administrator's connection to that same session and immediately display the working desktop is also important. It indicates that the user session and its applications have not simply terminated. However, as you have confirmed, that operation does not restore the session's ability to accept a subsequent normal RDP reconnect.
Given the amount of isolation you have already performed, I would not recommend continuing to change UDP/TCP transport settings, FSLogix, visual settings, keep-alive, or network-detection policies. The evidence now points toward a possible session reconnection/Winlogon state problem that requires deeper investigation.
At present, I cannot confirm from the published Windows Server 2025 known-issues documentation that this exact sequence has been identified as a known Windows Server 2025 issue. Likewise, I cannot find a publicly documented supported mechanism that resets this particular Winlogon/session state while preserving the user's running session.
Your Windows Server 2022 comparison is very valuable because it demonstrates a behavioral difference under apparently equivalent failure conditions. However, that comparison alone would not be enough to state that this is a confirmed Windows Server 2025 product defect. Establishing that would require analysis of the reproduction traces by Microsoft Support and, if necessary, the responsible product engineering team.
Unfortunately, for the same reason, I do not have a supported in-session recovery that I can recommend beyond what you have already tested. Task Manager > Users > Connect can be useful for emergency access, but it does not repair the session for the user's next external connection. I would also avoid terminating LogonUI, resetting the session, or manipulating Winlogon processes in production because these actions are not a documented recovery method for this condition and could leave the session unusable or result in loss of the user's work.
Therefore, if the session reaches this state, logging off the affected session remains the reliable way to return the user to a clean logon state until the underlying cause can be identified.
I realize this is probably not the definitive answer you were hoping for, particularly when you need to make a decision about continuing the Server 2025 migration. However, based on the troubleshooting you have already completed, I believe you have reached the point where further investigation goes beyond what can be reliably provided through a Microsoft Q&A thread.
Microsoft Q&A is a community technical Q&A platform. Within the forum, I can help with documented product behavior, configuration, published known issues, and supported troubleshooting guidance. However, a case such as this requires analysis of TSS/ETL traces, process dumps, and the internal Winlogon/RDS state at the exact point of failure. That level of debugging cannot be performed or validated through the forum.
I also do not want to speculate about undocumented Windows internals or present an assumption about the Winlogon notification sequence as an official root cause. Unless a behavior, defect, fix, or workaround has been publicly documented by Microsoft, or confirmed through the appropriate support/product channel, there is no reliable way in Microsoft Q&A to state whether the behavior is a product regression or what code-level condition is responsible for it.
For this reason, the one next step I recommend is to open a Microsoft Support case and provide the reproduction data you have already collected.
If possible, reproduce the interrupted Automatic Reconnection while that trace is running and retain the exact timestamps for the interrupted reconnect, Winlogon event 4008, and the subsequent connection that becomes stuck at Please wait. Include the RdpCoreTS, LocalSessionManager, RemoteConnectionManager, Winlogon/Application and Winlogon/Operational evidence, together with the dumps you have already collected.
I would also provide the equivalent Server 2022 reproduction where the interrupted reconnect occurs but the following reconnect succeeds. That side-by-side comparison should be especially useful in determining whether the behavior represents a Server 2025-specific regression.
Your investigation is already very thorough. At this stage, I would preserve the environment in which you can reproduce the problem rather than introduce additional configuration changes before collecting the support trace.
I am sorry that I cannot provide a definitive fix from the forum. In this case, however, escalating the reproducible trace to Microsoft Support is the most appropriate way to obtain the product-level analysis needed to determine whether a servicing fix or another supported mitigation is required.
References:
Windows Server 2025 known issues and notifications | Microsoft Learn
Troubleshoot Unexpected RDS Session Locks or Disconnections - Windows Server | Microsoft Learn
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