When attempting to sign in on a macOS using Okta Verify, the following error is encountered:

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• Okta Identity Engine (OIE)
• Multi-factor Authentication (MFA)
• Devices
• Okta Verify for macOS

• For security reasons, Okta does not allow for the inspection or modification of traffic between Okta Verify and its endpoints.
• A VPN is enabled.

1. First, collect Okta Verify Logs from Desktop (macOS / Windows).
2. Check the specific timestamp of the error, and if there are any of these errors in the logs:
   
   Sample Okta Verify logs: 
   
   

   {🛑 "Loopback": {"message": "Error during authentication flow: accountNotFound", "defaultProperties": "", "location": "LoopbackRequestHandler.swift:handle(_:completion:):64"}} {🛑 "Loopback": {"message": "Connection3: HandleLoopback complete failed with: Bad request", "defaultProperties": "", "location": "ServerConnection.swift:processChallengeRequest(request:success:failure:):242"}} {🛑 "Storage error": {"message": "Error: itemNotFound", "defaultProperties": "", "location": "OktaKeyValueStorageManager+Enrollments.swift:enrollmentKeys():264"}}

   
   To ensure proper functionality, it is a must to bypass Okta URLs from any SSL inspection tools. Because the agents utilize SSL pinning, SSL inspection will disrupt all related flows.

• If a VPN is enabled, this Tool acts as a man-in-the-middle tool, inspecting or blocking certain traffic. Okta Agents all utilize SSL Pinning, which helps mitigate man-in-the-middle attacks.
• Admin does not need to turn off the VPN, but it is recommended to ensure that the network does not inspect traffic for Okta Domains. Please consult with the Network Team.
• Alternatively, refer to the solution mentioned in the following article: Unable to Enroll Okta Verify on Windows - "The sign-in URL is not secure" or "Generic enrollment error".