Methods and apparatus for forwarding Caller ID data on demand when retrieving messages from an answering device using an endpoint telecommunications device and an associated call control system (such as the central office of the calling phone, a PBX, ToL Gatekeeper, wireless carrier switch, etc.), to fully or partially automate the dialing process for remotely calling back a message sender. The invention permits the caller retrieving messages to quickly and easily return calls with little or no manual intervention, without having to create a trombone connection. The invention operates with calling endpoint telecommunication devices that are "intelligent" enough to receive, store and/or utilize Caller ID data forwarded from an answering device; as well as with not so intelligent telecommunications devices (such as many pay phones) that may lack the ability to receive, store and/or utilize forwarded Caller ID data.