Your AI Now Speaks Up: Proactive Agent Notifications in Chat

v1.0.48 · Released 2025-01-31

Up until now, Sidekick worked when you asked it to. Need a summary of your inbox? Ask. Want to check your CI status? Ask. That's useful — but it's still reactive. You had to remember to check.

With v1.0.48, that changes. Sidekick's agent now monitors your connected services in the background and comes to you when something needs attention.

The Problem It Solves

Information overload is a distribution problem as much as a volume problem. The important signals — a stalled email thread, a broken build, a calendar double-booking — are buried inside a dozen different tools, each with its own notification system competing for your focus.

A capable assistant shouldn't wait to be asked. It should know what matters and surface it at the right time.

What's New

Proactive notifications appear in the Sidekick chat as agent-initiated messages. The agent watches for four categories of signal across your connected services:

Unanswered emails that have sat too long without a reply
Upcoming deadlines from your calendar and task integrations
Failed CI builds in your connected repositories
Calendar conflicts that need to be resolved

When the agent spots something, it sends a message into the chat with a plain-language summary and a set of suggested actions — reply, reschedule, rerun, dismiss — so you can act without leaving Sidekick.

Built for Your Workflow

Not every team runs at the same tempo, and not every notification should land in the same place. That's why this release ships with two key configuration options:

Notification frequency lets you choose between real-time alerts, hourly batches, or a single daily digest. High-urgency signals can still break through immediately while lower-priority items get rolled up.

Notification channels let you route different alert types to different surfaces — CI failures to a shared dev channel, email alerts to your personal thread.

What Comes Next

This release covers the four highest-signal notification categories. Future releases will expand coverage to more integration types and introduce smarter prioritisation — so the agent gets better at knowing not just what to surface, but when.

Proactive notifications are available now on all Sidekick plans. Head to Settings → Agent → Notifications to configure your preferences.