Okta Verify for Windows fails to update automatically when a firewall, proxy, or Secure Sockets Layer (SSL) inspection blocks traffic to the Okta allowed IP addresses. Resolve this error by allowing HTTPS traffic on port 443 to the required Okta IP addresses. The Okta Verify logs on the affected devices repeatedly display the following error:

ApplicationInstaller: Auto Update will not happen due to exception: System.Net.Http.HttpRequestException ... System.Net.Sockets.SocketException (A connection attempt failed because the connected party did not properly respond after a period of time ...)

• Okta Identity Engine (OIE)
• Okta Classic Engine
• Okta Verify for Windows

Okta Verify attempts to reach the update server over HTTPS on port 443, and the connection times out at the network level. If a firewall, proxy, or SSL inspection blocks or restricts traffic to Okta allowed IP addresses, this error occurs and the automatic update fails. If the organization has several network environments, specific environments may lack the allowlist. Devices on the allowed networks update successfully, while devices on the restricted networks fail to update.

How is the network timeout error resolved?

Confirm the error in the Okta Verify logs, adjust the network settings to allow HTTPS traffic to Okta IP addresses, and verify that the automatic updates complete successfully.

1. Set the Okta Verify LogLevel to Debug in the Windows registry.
2. Reproduce the update failure on the affected device.
3. Save the Okta and Okta Authenticator Service logs from the Event Viewer.
4. Collect the Windows installation logs from C:\Windows\Temp and the user's AppData\Local\Temp folder.
5. Check the logs to confirm the presence of the network timeout error.
6. Review the firewall, proxy, and SSL inspection settings on every network utilized by the affected devices.
7. Allow HTTPS traffic on port 443 to the Okta allowed IP addresses.
8. Exclude the Okta IP addresses from SSL inspection.
9. Confirm that the automatic updates complete successfully and the error no longer appears in the logs.

Related References

• Collect Okta Verify Logs From macOS and Windows Desktops
• Allow access to Okta IP addresses