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Dropbox client does not work if HTTPS Inspection is enabled
  • With HTTPS inspection is enabled, the Dropbox client does not work.

  • Packet captures shows a successfully established SSL handshake (Firewall - Server), but when we are trying to establish SSL handshake (Firewall - Client), the Client is sending back Fatal Alert, causing connection to close with:

    Alert (Level: Fatal, Description: Unknown CA)


In Outbound HTTPS Inspection, the Security Gateway's CA used to generate certificates needs to be installed as Trusted Root.

Dropbox client does not use host machine's trusted root authorities. Therefore, Security Gateway with enabled HTTPS Inspection will not be trusted, which causes Dropbox client to drop the connection.

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