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Troubleshooting: WatchOS App stuck on “Waiting for authentication”

If Habitify on Apple Watch keeps showing “Waiting for authentication”, make sure iCloud Keychain is enabled on both iPhone and Apple Watch and they are signed into the same Apple ID.

Written by Habitify
Updated this week

Why this happens

Habitify’s Apple Watch sign-in is synced from your iPhone via iCloud Keychain. If iCloud Keychain is turned off on either device (or the Watch and iPhone are not using the same Apple ID), the Watch app may remain stuck on “Waiting for authentication”.

Fix: Enable iCloud Keychain

Step 1: On your iPhone

  1. Open Settings on iPhone

  2. Tap [your name]iCloud

  3. Tap Passwords & Keychain

  4. Turn ON Sync this iPhone (iCloud Keychain)

Step 2: On your Apple Watch

  • Make sure your Watch is signed into the same Apple ID as your iPhone

  • Confirm Keychain is enabled for the Watch (if available in your watchOS settings)

Tips to complete authentication

  • Keep the iPhone near the Watch (Bluetooth on)

  • Keep Habitify open on the iPhone for 2–5 minutes during the first sync/auth

  • Re-open Habitify on the Watch after enabling Keychain

If it still doesn’t work

  1. Restart both your iPhone and Apple Watch

  2. Open Habitify on iPhone first, then open Habitify on Watch

  3. If needed, reinstall the Watch app and try again

If the problem persists, please contact us with your iPhone model, Apple Watch model, watchOS version, and a short video of the issue.


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