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Comparison · Comms

Session vs Twilio

Side-by-side trajectory, velocity, and editorial themes.

S
Session
COMMS
0.0

Session shipped a protocol rewrite and a paid tier, then went publicly broke — the founder is asking users to bail it out.

◆ Current state

Session is simultaneously in its most ambitious technical phase and an open funding crisis. Protocol V2 — re-implementing forward secrecy and layering post-quantum cryptography on top of Session's onion-routed transport — has been announced, and the Session Pro paid tier exited beta planning into a December development update. Then in March, cofounder Chris McCabe published a personal appeal saying the project cannot continue developing without user support, and the public feed has been quiet since.

◆ Where it's heading

The product roadmap that was meant to fund itself via Session Pro is colliding with the underlying problem the appeal makes plain: the Loki/Oxen-era token economics and donations aren't covering ongoing development. Protocol V2 and Pro are the bets that have to land for Session to remain viable; if Pro doesn't convert a meaningful share of the user base, the next twelve months are about scope reduction, not feature growth. The Feb 1 APT key rotation in January suggests the core infrastructure is still being maintained — for now.

◆ Prediction

Watch for either a hard Session Pro launch and conversion announcement, or a more explicit wind-down / handoff post. A long stretch of silence after a funding appeal usually resolves one way or the other within a quarter; the absence of any new posts since mid-March is itself a signal.

Twilio logo
Twilio
SUPPORTCOMMS
8.8

Twilio reframes itself as the conversation layer for AI agents, not just a messaging API.

◆ Current state

Twilio just shipped a coordinated batch of GA launches anchored on a new Conversations layer: Agent Connect SDK, Conversation Memory, Conversation Intelligence, Enterprise Knowledge, and Conversation Relay Insights all moved to GA on the same day. Alongside that, Apple Messages for Business is in private beta and a Bulk Messaging API is in public beta. The platform's center of gravity has clearly shifted from raw channel APIs to an AI-agent orchestration stack sitting on top of them.

◆ Where it's heading

Twilio is repositioning the company as the runtime where customer-facing AI agents live — owning memory, intelligence, channel reach, and observability, not just message delivery. The packaging is deliberate: each piece is shippable alone, but together they form an opinionated stack that competes head-on with Salesforce/Genesys agent platforms and with developer-first stacks like LiveKit. Expect Twilio to push hard on lock-in through Conversation Orchestrator as the binding layer.

◆ Prediction

Next likely moves: GA for Apple Messages for Business, and an expansion of the Agent Connect SDK toward third-party LLM and tool integrations to position it as the de-facto agent runtime on top of Twilio's channels. A Bulk Messaging GA and pricing for the AI features should follow within one to two quarters.

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