Systems and methods involve receiving a connectivity subscription request for one or more connections, such as a virtual private network (VPN) connection. A connectivity subscription request may be received through an application programming interface (API) call and the connectivity subscription request may indicate that a user associated with a connection wants to receive a notification when a connectivity event occurs. A connectivity event can occur when changes to the connection are detected, such as when the connection becomes active, when the connection becomes inactive, or when one or more tunnel connections related to the connection becomes disconnected. A potential problem associated with the connectivity event may be detected and a potential solution to the problem may be determined. The potential solution can be sent to a user associated with the connectivity event.