Get set up with Hindsight

What you’ll set up

This guide walks through a clean first setup for Hindsight on your Mac. By the end, Hindsight should be installed, activated or running on trial, allowed to capture the data you choose, and ready to search your timeline.

You’ll set up:

• The Hindsight app in Applications.
• The first-run onboarding flow.
• Screen capture and local OCR.
• App and window context through Accessibility.
• Audio transcription with a local model.
• Notifications for important capture and permission issues.
• A quick check that the timeline is recording normally.

Download and install Hindsight

1. Download the latest Hindsight.dmg from the public release page.
2. Open the DMG.
3. Drag Hindsight into Applications.
4. Eject the DMG after the copy finishes.
5. Open Hindsight from Applications.

Opening Hindsight from Applications is important. It makes macOS treat Hindsight as an installed app, which helps permissions and updates behave normally.

If macOS warns that the app was downloaded from the internet, choose Open if you trust the download source. If macOS blocks the app, open System Settings, go to Privacy & Security, and allow Hindsight from the security prompt.

Start the first-run flow

Hindsight runs as a menu bar app. After launch, look for Hindsight in the menu bar and follow the setup window.

During setup, Hindsight may ask you to start a free trial or activate a license. You can start the trial first and activate later, or enter your license key if you already have one.

If you have a license key:

1. Open the activation window when Hindsight asks for a license.
2. Paste the key exactly as it appears in your purchase receipt.
3. Keep your Mac online while activation validates.

If activation fails, confirm the key in your Lemon Squeezy order history and try again.

Grant Screen Recording

Screen Recording is required for Hindsight to capture your display and run local OCR over visible text.

1. Open System Settings.
2. Go to Privacy & Security.
3. Open Screen & System Audio Recording.
4. Enable Hindsight.
5. Quit and reopen Hindsight if macOS asks you to restart the app.

Without this permission, Hindsight can’t build a visual timeline.

Grant Accessibility

Accessibility lets Hindsight understand app and window context. It also helps Hindsight detect private browser windows so they can be skipped automatically.

1. Open System Settings.
2. Go to Privacy & Security.
3. Open Accessibility.
4. Enable Hindsight.
5. Return to Hindsight after the permission is enabled.

If you want Hindsight to skip Chrome Incognito and Safari Private windows, keep this permission enabled.

Enable audio capture

Audio capture lets Hindsight transcribe what you hear locally on your Mac. Audio search depends on both permission and a downloaded transcription model.

1. Enable Hindsight in Screen & System Audio Recording when macOS asks.
2. Continue through onboarding until you reach transcription setup.
3. Download the default English transcription model.
4. Wait for the model download to finish before relying on audio search.

The default model is the fastest option to get started. Larger models can improve language coverage and accuracy, but they use more disk space and can run slower.

Allow notifications

Notifications are used for important status changes, such as capture pausing because a permission changed.

1. Allow notifications during onboarding.
2. Open Hindsight settings later if you want to fine-tune notification behavior.
3. If notifications are blocked, re-enable them in macOS System Settings.

Notifications are not required for search, but they make setup and troubleshooting easier.

Review privacy settings

Before you let Hindsight run all day, review what should and should not be captured.

You should check:

• Apps that should never appear in your timeline.
• Whether private browser windows should be skipped.
• Whether capture should pause while your Mac is on battery power.
• How much local history you want to keep.

Hindsight is designed to process and store your timeline locally. You still control what the app is allowed to capture.

Confirm capture is working

After onboarding is complete:

1. Open a normal app or browser window.
2. Wait a short moment for Hindsight to capture.
3. Open the Hindsight timeline from the menu bar.
4. Search for a word that was visible on screen.
5. Open a result and confirm it takes you back to the expected moment.

For audio, play or join something with speech after the transcription model has downloaded, then search for a phrase from that audio once Hindsight has had time to transcribe it.

If the timeline is empty

Check these items first:

• Hindsight is running in the menu bar.
• Screen Recording is enabled for Hindsight.
• Hindsight was reopened after permission changes.
• Capture is not paused in Hindsight settings.
• Battery settings are not blocking capture while unplugged.
• The current app is not excluded from capture.

If audio is missing, also confirm a transcription model has finished downloading.

If private windows are missing

That is expected when private-browser skipping is enabled. Hindsight can skip Chrome Incognito and Safari Private windows so sensitive browsing does not enter your timeline.

If you intentionally want those windows captured, review the privacy controls in Hindsight settings before changing the rule.

Keep Hindsight updated

Hindsight uses direct app updates. Keep automatic update checks enabled so you receive compatibility, reliability, and security fixes.

When an update is downloaded, quit Hindsight when prompted so the new version can install.

What to note before asking for help

If setup still does not work, write down:

• Your macOS version.
• Your Hindsight version.
• Which permission or setup step is failing.
• The exact message macOS or Hindsight shows.
• Whether the issue affects screen capture, audio transcription, search, licensing, or updates.

Those details make setup issues much faster to diagnose.