VPN Gateway: Point-to-Site Connection Issue — TLS Handshake Failure Due to Expired Certificate

PawelC-5712 0 Punkty reputacji
2026-10-20T17:53:25.59+00:00

Problem description

I am experiencing a problem with my Azure VPN Gateway's Point-to-Site (P2S) connections. The VPN client is failing to establish a connection, with the error indicating a failure to complete the TLS handshake because the received certificate has expired.

Environment

Azure VPN Gateway used for Point-to-Site remote access

Tunnel type: OpenVPN,

Authentication type: Microsoft Entra ID,

Client OS: Windows,

Client OS version: 26H2.

What I've already tried

I have downloaded a new VPN client profile approximately 40 minutes before attempting to connect.

I verified that my device's date and time are correct and synchronized.

I also checked connectivity from different locations within Poland, ruling out ISP issues.

Additionally, I reviewed the diagnostic snapshot and noted planned gateway maintenance, which could cause brief disconnects but not the persistent TLS handshake failure.

In P2S configuration i have properly configured sts url with trailing slash /

Current status

The issue persists with the latest tests, and the connection still reports an expired certificate during the TLS handshake.

I am seeking guidance on how to resolve this certificate expiration problem and ensure successful P2S VPN connectivity.

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