Troubleshooting

Having trouble with Sidetrip? This guide covers common issues and their solutions.

iCloud Sync Issues

Trips Not Appearing on Other Devices

Symptoms: A trip created on one device doesn't show up on another

Solutions:

1. Check iCloud is enabled for Sidetrip:
   • Go to Settings → [Your Name] → iCloud on each device
   • Scroll down and ensure Sidetrip is toggled on
2. Verify the same iCloud account: All devices must be signed into the same iCloud account
3. Check your internet connection: iCloud sync requires an active connection
4. Wait a few minutes: Initial sync after enabling iCloud can take a few minutes
5. Restart the app: Close Sidetrip completely and reopen it to force a sync check

Changes Not Syncing

Symptoms: Edits made on one device don't appear on another

Solutions:

• Ensure both devices have an active internet connection
• Open Sidetrip on the device that should receive the update — the app fetches changes when it opens
• Check that iCloud is not paused due to low storage on your iCloud account

Apple Watch Issues

Trips Are Not Appearing on Apple Watch

Symptoms: The Watch app shows no trips or an empty library

Solutions:

1. Confirm Sidetrip Pro is active. The Apple Watch companion requires Pro.
2. Make sure the Watch and the iPhone or Mac that has your trips use the same iCloud account.
3. Open Sidetrip on your iPhone or Mac and confirm the trips are visible and not archived.
4. Check that Sidetrip is enabled in iCloud and that the Watch has an active Wi-Fi or cellular connection.
5. Open the Watch app again and wait for the initial iCloud sync to finish.

Apple Watch Shows "Sidetrip Pro Required"

Symptoms: The Watch app shows a locked screen instead of your trips

Solutions:

1. Purchase or restore Sidetrip Pro in Sidetrip on your iPhone, iPad, or Mac.
2. Verify the main app and Watch use the same iCloud account.
3. Wait for iCloud to sync the Pro access state, then tap Try Again on the Watch.

Apple Watch Changes Are Not Syncing

Symptoms: A visit-status change made on the Watch is not visible elsewhere

Solutions:

• Check the Watch has a Wi-Fi or cellular connection.
• Open Sidetrip on another device to allow iCloud changes to be fetched.
• Confirm the trip is not read-only and that you have permission to edit it.
• Open the Watch app again after the connection returns.

Import Issues

Import Fails with "Invalid JSON" or Another Format Error

Symptoms: Error when trying to import a trip file

Solutions:

1. Let the AI fix it: The error message says what's wrong and where (for example, a line number or a field such as trip.parts[0].days[2].stops[1].time). Tap Copy for AI, paste it into the AI chat that created the JSON, and import the corrected reply
2. Check the JSON is complete: AI assistants sometimes truncate long responses. Ask the AI to continue or regenerate a shorter version (fewer days)
3. Verify the schema version: The JSON must include a "version" field at the top level, such as "version": "2.1"
4. Copy only the JSON: Sidetrip removes a ```json code fence around the JSON automatically, but any other text before or after it — like "Here's your trip:" — must be left out
5. Check the dates: All dates must use the YYYY-MM-DD format, such as 2026-04-15
6. Validate the JSON: Paste the JSON into a free online JSON validator to check for syntax errors before importing

Import Fails with "Duplicate Trip"

Symptoms: Message saying a trip with that ID already exists

Solutions:

• Sidetrip detected that you're importing a trip whose ID matches one you already have. You'll be asked if you want to Update the existing trip with the new data. Visit statuses for matching stops are kept; everything else, including notes, comes from the file.
• If you want a separate copy, edit the id field at the top of the JSON to a new unique value before importing.

Update Trip Says the File Is for a Different Trip

Symptoms: Using ⋯ → Update Trip in a trip shows an error about a different trip

Solutions:

• Update Trip only accepts a file with the same trip id as the open trip. Make sure you picked the right file, or that the AI kept the original id when it edited the JSON.
• To add the file as a new trip instead, import it from the + button on the trips list.

Imported Trip is Missing Stops or Accommodations

Symptoms: The trip imports but some content is absent

Solutions:

• The source JSON may be incomplete. Check the raw JSON to verify all stops are present in the data
• If you generated the JSON with an external AI, ask it to regenerate or complete the missing sections

AI Generation Issues

Apple Intelligence Generation Is Not Available

Symptoms: The Apple Intelligence section is missing, shows a message, or Generate Trip is disabled

Solutions:

• AI generation requires iOS 26 / macOS 26 or later. On earlier OS versions, the Apple Intelligence section doesn't appear.
• On iOS 26 / macOS 26 or later, read the message in the section. It tells you if your device doesn't support Apple Intelligence, if it's turned off (enable it in Settings → Apple Intelligence & Siri), or if the model is still downloading (keep the device plugged in and on Wi-Fi).
• On iOS 27 / macOS 27 or later, the section also shows when Apple's daily Private Cloud Compute limit has been reached, with any usage options Apple offers.
• Generation is available to Free and Pro users within their existing trip limits. Pro is not required for generation itself.
• Use Generate with External AI as an alternative on any device.

Generation Fails or Stops Partway Through

Generation uses Apple Private Cloud Compute (PCC) exclusively on iOS 27 / macOS 27 or later and remains local on iOS 26 / macOS 26. Sidetrip shows failures without silently switching models or processing locations.

Symptoms: Error message during generation, or progress stops and doesn't complete

Solutions:

1. Check PCC access on OS 27+: Generation requires an internet connection. For availability errors, try again when the service is available. If Apple's daily quota is reached, wait for it to reset. The quota is independent of Sidetrip Pro; upgrading does not increase or remove it.
2. Retry local generation on OS 26: On-device AI can occasionally time out. Tap the retry button.
3. Simplify the description: A very long or complex prompt can push the model to its limits. Try a shorter description or reduce the number of days.
4. Restart the app: Close Sidetrip and reopen, then try generating again.
5. Use Generate with External AI: If generation consistently fails, you can choose to use an external AI to generate the JSON instead. Sidetrip never switches to an external AI automatically.

AI Assistant Issues

AI Assistant Is Not Available

Symptoms: The assistant button doesn't appear in the toolbar

Solutions:

• The AI assistant requires iOS 26 / macOS 26 or later on a device that supports Apple Intelligence, plus Sidetrip Pro.
• On a trip shared with you, the assistant appears only if you have permission to make changes. It's hidden on view-only trips.

Private Cloud Assistant Is Unavailable

Symptoms: The Private Cloud assistant shows a message instead of the message field, or a request fails

Solutions:

• Private Cloud requires iOS 27 / macOS 27 or later and an internet connection. Check your connection and try again.
• If Apple's daily Private Cloud Compute limit has been reached, the assistant shows when usage resets. Trip generation uses the same limit. Sidetrip Pro does not increase it.
• Tap Switch to On Device to keep editing offline. The On Device assistant edits the trip's details from the trip overview and a single day from a day view.

Assistant Doesn't Understand My Request

Symptoms: The assistant asks for clarification repeatedly, or makes the wrong change

Solutions:

• Be more specific: include the exact name of the stop or day you're referring to
• Break complex requests into smaller steps: one change at a time tends to work more reliably
• If an incorrect change was made, ask the assistant to reverse it in the same session

Session Limit Reached

Symptoms: Message saying the session has reached its limit

Solutions:

• Tap New Session to start a fresh conversation. All changes from the previous session are saved to your trip.

Cover Photo Issues

Generate with AI Is Missing or Disabled in the Cover Editor

Solutions:

• AI-generated covers require iOS 27 / macOS 27 or later. On earlier versions, the option doesn't appear.
• The option is disabled when Image Playground isn't available on your device. You can still use Choose Photo or Choose File.
• AI-generated covers require Sidetrip Pro; photos and files are free.

I Can't Add a Cover

Solutions:

• Add Cover appears only when you can edit the trip. On a view-only shared trip, ask the owner to add it.
• Covers added by others appear after iCloud sync. Make sure both devices are online.

Launch Issues

Sidetrip Doesn't Open My Current Trip at Launch

Solutions:

• Check that Settings → Trips → Open Current Trip at Launch is on. To open today's day rather than the overview, also turn on Open Today's Day.
• Today must fall between the trip's start and end dates, and the trip must not be archived.
• The trip opens when the app launches, not when you switch back to Sidetrip while it's still running. Opening Sidetrip from a share invitation also shows the trips list.
• If several trips overlap today, Sidetrip opens the one that started most recently.

Sharing Issues

Share Invitation Not Received

Symptoms: The person you invited doesn't see the share invitation

Solutions:

1. Verify the iCloud email: Confirm you used the correct iCloud email address for the recipient
2. Check their iCloud: The invitation may appear in the recipient's iCloud notifications rather than as an email. Ask them to check for a Sidetrip share notification.
3. Try the share link: In the trip overview, tap Manage Sharing, copy the link, and send it directly via Messages or Mail instead.
4. Wait a few minutes: iCloud invitations can take a few minutes to arrive.

Cannot Accept a Shared Trip

Symptoms: Tapping the share link shows an error or the trip doesn't appear

Solutions:

• Free tier trip limit: If you already have one trip and are on the free tier, you cannot accept another. Upgrade to Sidetrip Pro or remove your existing trip first.
• iCloud account mismatch: The share invitation is tied to the iCloud account the invitation was sent to. Ensure you're signed into that iCloud account on the device where you're accepting.
• Check internet connection: Share acceptance requires an active connection.

Shared Trip Shows Outdated Content

Symptoms: A shared trip you received doesn't reflect the owner's recent changes

Solutions:

• Ensure you have an active internet connection
• Close and reopen Sidetrip to trigger a sync
• If the issue persists, ask the owner to verify their changes synced from their device

Sidetrip Pro Issues

Pro Features Not Unlocked After Purchase

Symptoms: Purchased Pro but still seeing the free tier restrictions

Solutions:

1. Wait a moment: Purchases sometimes take a few seconds to register
2. Close and reopen the app: This refreshes your Pro status
3. Restore purchases:
   • Go to Settings
   • Tap Restore Purchases
   • Wait for confirmation
4. Check your Apple ID: Confirm you're signed into the App Store with the Apple ID used for the purchase

Cannot Restore Purchase on New Device

Symptoms: Previously purchased Pro, but restore fails on a different device

Solutions:

1. Verify you're signed into the App Store with the same Apple ID used for the original purchase
2. Go to Settings → Restore Purchases in Sidetrip
3. If still unable to restore, check your purchase history in Settings → [Your Name] → Media & Purchases → Purchase History

Still Need Help?

If you've tried the above and still have an issue, contact support with:

• A description of the problem
• Steps to reproduce it
• Your device model and iOS/macOS version
• Your Apple Watch model and watchOS version, if the issue occurs on Watch
• Your Sidetrip version (visible in Settings)