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Troubleshooting

Updated

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

Import Issues

Import Fails with "Invalid JSON"

Symptoms: Error when trying to import a trip file

Solutions:

  1. Check the JSON is complete: AI assistants sometimes truncate long responses. Ask the AI to continue or regenerate a shorter version (fewer days)
  2. Verify the schema version: The JSON must include "schema_version": "2.0" at the top level
  3. Remove any markdown formatting: When pasting from an AI chat, make sure you're pasting only the raw JSON, not the surrounding code fence (` ```json ` ... ` ``` `)
  4. 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. This is safe — your visit statuses and notes for matching stops are preserved.
  • If you want a separate copy, edit the id field at the top of the JSON to a new unique value before importing.

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

Generate with AI Is Not Available

Symptoms: The "Generate with AI" option doesn't appear

Solutions:

  • AI generation requires iOS 26 / macOS 26 or later on a device that supports Apple Intelligence. On older OS versions or unsupported hardware, the option is hidden.
  • Confirm you have Sidetrip Pro — AI generation is a Pro feature.
  • Use the Copy Prompt workflow as an alternative on any device.

Generation Fails or Stops Partway Through

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

Solutions:

  1. Try again: On-device AI can occasionally time out. Tap the retry button.
  2. 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.
  3. Restart the app: Close Sidetrip and reopen, then try generating again.
  4. Use the Copy Prompt workflow: If on-device generation consistently fails, use an external AI to generate the JSON instead.

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.
  • If you're on a shared trip (Shared with Me), the assistant may not be available as the trip is owned by someone else.

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.

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: Use the Copy Link option and send the link 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

Pro Subscription 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 forces a subscription status refresh
  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 Sidetrip version (visible in Settings)