Systems, methods, and software can be used to process certificate validation warnings. In some aspect, a connection to a Virtual Private Network (VPN) server is initiated at an electronic device. The VPN server is associated with a VPN profile. In response to initiating the connection, a certificate associated with the VPN server is received at the electronic device. A validation warning associated with the certificate is received. A fingerprint of the certificate is generated. A validation action is selected based on the validation warning, the fingerprint, and the VPN profile. The selected validation action is executed.