2.5 is a big one :) Sidekick has a new home, a conversation that stays with you, and a much smoother way to work across your Mac.
A proper home for Sidekick
The new chat brings your prompts, replies, and ongoing work into one continuous conversation. Pick up where you left off, search your history, or reply to a specific part of an answer.
You can keep chatting. Sidekick automatically summarizes older messages in the background, so you don't need to manage conversation length. If you do want to clear your chat, your knowledge base and saved Sidekick instructions stay.
Everything feels more Sentient: deep blacks, slowly moving signature colors, a little grain, and liquid glass. Proactive cards have more room to breathe and tuck into their dock as you scroll. Settings opens from its button, and the home screen gives your work more space.
See the work. Stay in your flow.
Expand Worked for… to see the apps Sidekick used and the steps it took, right inside the conversation. Live activity follows along as it works, with app icons and clear updates like “Looking at an app” and “Clicking.” The notch gets those same updates with both ChatGPT and Claude.
When Sidekick asks a question, you can answer directly in the notch. No need to leave what you're doing. Open in Sentient is there when you want the full conversation.
Proactive card actions now start working in chat, so the request, progress, and result live together.
More resilient computer use
We've put a lot of work into the moments where an app takes a beat to open, a window moves, your click interrupts typing, or the connection briefly drops. Sidekick can read fresh state and recover instead of treating every tool hiccup as the end of the task. It checks what already happened before repeating an action.
This update also improves long-running tasks, ChatGPT and Claude activity reporting, and automatic handoff from a lingering ChatGPT Computer Use helper.
If something really isn't working, Test & repair in Permissions & Health checks Sentient's own test window and gives you clearer evidence of the problem. Sidekick only offers this as a last resort after repeated failures across apps and confirmed permissions, and asks before opening the window. You can review the technical report and choose whether to send it to us. Reports exclude screenshots, chat content, and document contents.
Ready sooner. Easier to discover.
- Use Sidekick while your first analysis runs, or schedule analysis for overnight and get started right away.
- A visible Double Tap shortcut and a gentle ready hint help you find it when initial analysis finishes.
- Start analysis now even if you previously scheduled it for overnight.
- Choose your overnight wake time in Settings.
- Let another notch app handle clicks, and open Sidekick with your keyboard shortcut instead.
- Clearer onboarding guidance points at your actual notch, and smaller MacBook screens keep their controls in view.
- Find Give AIs Knowledge inside your knowledge base, with less clutter on the home screen.
Thank you for all the feedback, bug reports, and very specific opinions about pixels. They made this release much better :D
October 19 refresh: This download now includes the FINAL_1000 courtesy-gift flow, with the gift animation and a note from us for people who missed the lifetime offer. Existing lifetime access stays intact. This replaces the 2.5 download and keeps build number 14.
Sentient OS 2.5 (build 14). Requires an Apple silicon Mac running macOS 15.4 or later.