Troubleshooting

Tasks won't start — Terminal permission denied

Sightdeck AI launches each Claude session in a Terminal window. macOS requires explicit permission to let one app control another. If you click Start and nothing opens — or you see an "operation not permitted" message — the Automation permission is missing.

1. Open System Settings → Privacy & Security → Automation.
2. Find Sightdeck AI in the list and make sure the toggle next to Terminal is on.
3. If Sightdeck AI is not in the list at all, go back to the app, hover any backlog task and click Start. macOS shows the permission prompt — click OK.
4. Try starting the task again.

The board does not update — Files & Folders permission

If the board looks stale — tasks do not flip to active or done even though Claude has finished — Sightdeck AI may not be able to watch the task file for changes. This usually happens when your project folder is inside ~/Documents, ~/Downloads or ~/Desktop.

1. Open System Settings → Privacy & Security → Files & Folders.
2. Find Sightdeck AI and check that the relevant folder is toggled on.
3. If nothing is listed, restart Sightdeck AI. macOS prompts the first time the app tries to watch a file in a protected location.
4. Grant access in the prompt, then check the board again.

Skill not triggering — tasks appear in the terminal but not in the app

If Claude runs your request but no task appears in Sightdeck AI, the skill is either not installed or not wired up to the project.

1. Open the app, go to Setup, and check whether the Install Skill step is green. If not, click Install to reinstall.
2. Open your project in Claude and send any message (for example, "hello"). The skill wires itself in on first use — the task you asked for appears on the board in the app, which confirms it worked.
3. If the task still does not appear, update Claude Code to the latest version (old versions can silently ignore the skill), then try again.

App won't open after install

macOS blocks apps downloaded from the internet until you explicitly allow them.

1. Open System Settings → Privacy & Security and scroll to the bottom of the page.
2. You should see a message that Sightdeck AI was blocked. Click Open Anyway.
3. macOS asks one more time — click Open in that dialog.

If there is no "Open Anyway" button, right-click the app in Finder and choose Open from the context menu instead of double-clicking.

License activation failed

The app verifies your license key once online when you first paste it. A few things can stop this from working.

1. Check that you are connected to the internet. The verification is a single outbound call and takes a second or two.
2. Make sure you pasted the full key with no leading or trailing spaces. Copy it directly from your purchase email or the thank-you page.
3. If you bought a license and have not received an email after a few minutes, check your spam folder. The key is also on the thank-you page in your browser right after checkout.
4. If you have already activated on two machines and want to add a third, deactivate one of the existing machines first in your license settings.

If none of these steps resolve the issue, reach out via the contact page with your order email address and we will sort it out.

Task stuck in testing

A task stays in testing when Claude is still running tests, or when the tests stopped without telling the app they finished. Both are recoverable.

1. Check the Terminal window for the task. If tests are still running, wait for them to finish.
2. If the terminal session has ended but the task is still in testing, open the task's detail panel and use the status selector to set it back to active. Claude can then pick up and re-verify.
3. If the task stays stuck, read the last history entry in the detail panel, look for a test-runner error, fix it, and click Start again to run a fresh session.

Notifications — done banner not appearing

The banner when a task completes is optional and depends on macOS notification permission. If you never saw the prompt, or dismissed it and want it back:

1. Open System Settings → Notifications.
2. Find Sightdeck AI and set it to Allow Notifications.

Declining this permission has no effect on task launching or board updates — only the done banner is affected.

Still stuck?

If a problem is not listed here or the steps above did not resolve it, use the contact page. Include the app version, your macOS version, and a short description of what you did and what happened.