A device can receive, from a user device, a hypertext transfer protocol (HTTP) CONNECT request associated with a toll-free data service. The user device can establish a first transmission control protocol (TCP) connection with a proxy server. The HTTP CONNECT request can request the proxy server to establish a second TCP connection with a content provider server. The device can determine, based on the HTTP CONNECT request, that an authorization condition is satisfied. The device can store information associated with a flow between the user device and the content provider server. The user device and the content provider server can establish a transport layer security (TLS) connection based on the first TCP connection and the second TCP connection. The device can provide the information associated with the flow to permit an account of an entity to be adjusted in association with the toll-free data service.