Sidekick Now Proactively Alerts You — No Prompting Required

v1.0.44 — Proactive Agent Notifications in Chat

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Until now, Sidekick worked on demand: you asked, it answered. That's still true — but starting with v1.0.44, your agent doesn't wait to be asked.

The problem with on-demand AI

An assistant that only reacts is still leaving work on the table. Unanswered emails pile up. CI breaks go unnoticed for hours. A calendar conflict slips through until it's too late to fix. You'd have to remember to ask the agent about each of these — which defeats the purpose of having one.

What's new: agent-initiated notifications

Sidekick now monitors your connected services in the background and sends you proactive messages in the chat when it detects something that needs attention. No new app, no separate notification system — it shows up right where you already work with your agent.

Out of the box, the agent tracks:

• Unanswered emails — catches messages that have slipped through your inbox
• Upcoming deadlines — flags tasks and due dates before they become urgent
• Failed CI builds — alerts you to broken builds across connected repositories
• Calendar conflicts — spots overlapping meetings and proposes fixes

Every notification comes with suggested actions so you can act immediately — reply, reschedule, investigate, or dismiss — without switching context.

You control the volume

Not everyone wants the same level of interruption. Two settings let you dial in the right balance:

• Notification frequency — how often the agent checks and surfaces alerts (High, Normal, Low, or Off)
• Notification channels — which categories you actually want to hear about

Turn off CI alerts on weekends. Crank up email monitoring during a launch week. It adapts to how you work.

Available now

Proactive notifications are available to all Sidekick users starting today. Connect your services, check your notification settings, and let your agent start pulling its weight around the clock.