A voice communication controller (e.g., private branch exchange (PBX)) is described herein which can automatically enable an outbound dual tone multi-frequency (DTMF) feature for one of it's extensions that is attached to a phone which belongs to a user while that user is or is likely to be participating in a session with an external DTMF communication system (e.g., a conference/collaboration bridge, an interactive voice response (IVR) system, or a voice mail system). This is desirable because if the user presses button(s) on their phone then the voice communication controller which has enabled the outbound DTMF feature will not attempt to process the corresponding DTMF digit(s) but instead will automatically transfer the corresponding DTMF signal(s) to the external DTMF communication system.