The present disclosure relates generally to systems and methods for facilitating proactive two-way communication sessions. One example includes proactively sending a message, where when the message is received, the message initiates a conversation with a user across a first messaging platform. When it is dynamically determined that the first messaging platform is unavailable, a list of prioritized alternative messaging platforms is dynamically generated. A prioritized second messaging platform is selected from the list of prioritized alternative messaging platforms, and the message is dynamically modified in accordance with standards associated with the prioritized second messaging platform. When a response is then received after sending the modified message on the prioritized second messaging platform, an agent is selected from a pool of agents to respond.