The present invention provides systems and methods to automatically install and trust a self-signed (e.g., untrusted) web site certificate on one or more web clients local to the network. In addition, the systems and methods provide for automatic installation of the self-signed certificate and/or a signed (e.g., trusted) certificate on a web server, and automatic configuration to enable an authentication and/or encryption mechanism (e.g., SSL encryption) with at least a portion of the web site. Conventionally, certificate installation, configuration and trusting are achieved manually, which can be time consuming and prone to errors such as trusting a fictitious certificate, for example. The systems and methods of the present invention provide a novel approach to mitigate manual web site certificate installation (e.g., trusted and untrusted) and trusting, web client interruption via untrusted web site warning notifications, and domain web site redirection to a fictitious web site.