Welcome to the Microsoft Q&A Platform! Thank you for asking your question here.
Based on your description, I would like to offer some insights to help you understand the behavior you are encountering with Quick Assist.
The issue you are experiencing is expected behavior and not the result of a fault, misconfiguration, or specific VPN setup. It reflects broader updates aimed at strengthening how Quick Assist maintains session integrity and security.
We understand this change may be challenging, especially if you are used to the previous experience. However, this behavior is intentional and was introduced to enhance protection for users and organizations by enforcing stricter authentication and identity validation.
Recommendation:
For a more secure, consistent, and supportable remote assistance experience, we recommend transitioning to Remote Help.
Because Quick Assist is no longer recommended for enterprise use in managed environments. Hence, this solution is designed specifically for enterprise scenarios and offers enhanced identity verification, improved session control, and seamless integration with Microsoft Intune.
Learn more about Remote Help and how it can better support your enterprise needs:
🔗 https://learn.microsoft.com/en-us/mem/intune/remote-actions/remote-help
For broader context on the recent changes to Quick Assist, please refer to this Microsoft article:
I hope this information can help you. Wish you have a pleasant day!