Configuring ChatGPT Desktop App for macOS

Configuring ChatGPT Desktop App for macOS

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Note:
This step is only required if you are using a SASE-based deployment. If you are using the Lumia installers, no additional steps are needed to analyze ChatGPT Desktop App for macOS.
The ChatGPT macOS application uses Certificate Pinning, which prevents it from working with TLS inspection. This results in a "Network configuration issue" error when starting the application.
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To mitigate this, you must explicitly allow your SASE root certificate within the ChatGPT application. The steps below will guide you through adding your certificate's unique hash to the application's trusted list.
Before you begin
Please ensure you are using the latest version of the ChatGPT macOS app. Older versions do not support manual certificate overrides.

Implementation Steps

We recommend first validating these settings manually on a single machine. Once verified, this configuration can be deployed organization-wide via your MDM (e.g., Jamf or Kandji) as a shell script or a configuration profile.

1. Locate your SASE Root Certificate

To proceed, you will need the full path to your SASE root certificate file (e.g., /Users/yourname/Downloads/cert.pem).
follow our Locating your SASE Root Certificate guide to obtain the file before proceeding to the next step.

2. Generate your Unique Certificate Hash

  1. Download the LumiaBypassChatGPTPinning.sh1.2 KiB script (Right-click the link → "Save As..." and save it to your computer).
  2. Open Terminal and make the script executable:
    chmod +x ./LumiaBypassChatGPTPinning.sh
  3. Run the script by pointing it to your certificate file:
    ./LumiaBypassChatGPTPinning.sh [path_to_your_cert.pem]

3. Apply the Configuration

The script will output a command containing your unique hash. Run that command once in the Terminal (in the user's context, do not use sudo). The command will look like this:
defaults write com.openai.chat com.openai.pinned_cert_hash_list -array "YOUR_GENERATED_HASH"

4. Verification

To validate the configuration:
  1. Restart ChatGPT (Right-click the icon in the Dock and select Quit, then reopen the application).
  2. Confirm that the application functions correctly and that the "Network configuration issue" message no longer appears.
  3. Return to our Getting Started guide to view setup links for other applications, or proceed to Step 1.B to complete your integration.
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Need assistance? If you have questions or require help with your specific configuration, please reach out to your Lumia representative.