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dnedrow/privatevpncert.md

Created June 19, 2026 20:47
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Installing a VPN root certificate in macOS running in a VM
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privatevpncert.md

The problem

When running a tool like Parallels on a Mac that is connected to a VPN with a custom certificate, the hosted macOS cannot, in many cases, connect to the outside world. This may manifest as a TLS error.

The Solution

Installing the VPNs certificate in the virtualized macOS system keychain.

The Steps (inside the macOS VM, assuming Zscaler certificate)

  1. Open Keychain Access
  2. Drag or import the Zscaler root certificate into the system keychain, not the login keychain
  3. Double click the imported cert
  4. Expand the Trust section
  5. Set the trust option to Always Trust
  6. Close Keychain Manager and authenticate when prompted

Terminal Access

sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /path/to/zscaler.cer

Restart the virtual machine

Now, you should be able to access the network without TLS errors.

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