The Calendly integration in BoldDesk allows customers to schedule meetings from live chat workflows. When a meeting is scheduled, BoldDesk creates a ticket containing the meeting details. Rescheduling and cancellation updates are recorded in the same ticket.

This article explains how to resolve Calendly webhook, scheduling-time, and signature-validation errors in BoldDesk.

Prerequisites

Before troubleshooting, ensure that:

• The Calendly app is installed from Admin > Marketplace.
• A valid BoldDesk API key is configured in the Calendly app.
• The app configuration was completed using Verify & Save.
• The Calendly scheduling block is included in an active live chat workflow.
• The associated live chat widget and sticky button are active when sticky-button scheduling is used.

The BoldDesk Calendly integration currently supports meeting scheduling through live chat workflows. BoldDesk automatically tracks scheduled, rescheduled, and cancelled meetings in the related ticket.

Review the Calendly Configuration

Before resolving an error:

1. Go to Admin > Marketplace.
2. Search for and select Calendly.
3. Confirm that the app is installed.
4. Review the configured BoldDesk API key.
5. Click Verify & Save if the API key was changed.
6. Confirm that the applicable live chat workflow is published and active.

If the integration is disabled or not configured, BoldDesk ignores incoming Calendly webhook events, and meeting-related tickets are not created or updated.

Error Messages and Resolutions

Invalid Calendly Webhook Object

Error message
Invalid Calendly webhook object.

When It Appears

This error appears when BoldDesk cannot validate or process the Calendly webhook information received for a meeting event.
Calendly uses webhook events to notify connected applications when an invitee schedules, cancels, or reschedules a meeting. A scheduled meeting triggers an invitee.created event, while a cancellation triggers an invitee.canceled event. A rescheduled meeting generates both event types.

Resolution

1. Confirm that the Calendly app is installed and configured under Admin > Marketplace.
2. Confirm that the BoldDesk API key configured in the app is valid.
3. Click Verify & Save to validate the current configuration.
4. Confirm that the meeting event exists in Calendly.
5. Check the related BoldDesk ticket to determine whether the meeting was created, rescheduled, or cancelled despite the error.
6. Retry the affected scheduling action once.

If the error continues, contact BoldDesk Support and provide:

• BoldDesk organization URL or organization ID.
• Related chat conversation ID.
• Related ticket ID, if created.
• Calendly meeting or event link.
• Exact error message.
• Date, time, and time zone of the event.
• Whether the action was scheduling, rescheduling, or cancellation.

Start Time Must Be Before End Time

Error message
Start time must be before end time.

When It Appears

This error appears when the selected scheduling range has a start time that is equal to or later than the end time.
Calendly requires a valid availability range in which the start time occurs before the end time. Calendly also limits an available-time request to a maximum range of 31 days. Longer periods require separate availability requests.

Resolution

1. Return to the Calendly scheduling interface in the chat.
2. Review the selected date and time range.
3. Select a start time that occurs before the end time.
4. Confirm that both values use the intended date and time zone.
5. Submit the scheduling request again.

Valid example

• Start time: November 10, 2026, at 10:00 AM
• End time: November 10, 2026, at 10:30 AM

Invalid example

• Start time: November 10, 2026, at 11:00 AM
• End time: November 10, 2026, at 10:30 AM

If customers repeatedly receive this error from a live chat workflow:

1. Go to Admin > Chat > Chat Automation > Workflows.
2. Open the workflow containing Get Scheduler via Calendly.
3. Review the configured Calendly event or custom event URL.
4. Confirm that the intended event is active in Calendly.
5. Publish and activate the corrected workflow.

Start Time Must Be in the Future

Error message
Start time must be in the future.

When It Appears

This error appears when the scheduling request contains a start time that has already passed.
Calendly requires the start time used to retrieve or book available time slots to be in the future.

Resolution

1. Return to the Calendly scheduling interface.
2. Refresh the available time slots.
3. Select a future date and time.
4. Verify the time zone displayed in Calendly.
5. Submit the meeting request again.

If a recently selected time is reported as being in the past:

1. Compare the customer’s local time zone with the time zone displayed by Calendly.
2. Refresh the scheduling page to remove expired time slots.
3. Select another available future slot.
4. Retry the booking.

Calendly Webhook Signature Validation Failed

Error message
Calendly webhook signature validation failed. Please reconnect Calendly and try again.

When It Appears

This error appears when BoldDesk cannot verify the authenticity of a webhook event received from Calendly.
Calendly signs webhook events using a shared signing key and sends the signature in the Calendly-Webhook-Signature header. The receiving integration compares the supplied signature with the expected signature to confirm that the event originated from Calendly and was not modified.

Resolution

1. Go to Admin > Marketplace.
2. Search for and open Calendly.
3. Review the current integration configuration.
4. Reconnect or reconfigure Calendly using the available app controls.
5. Confirm that the BoldDesk API key is valid.
6. Click Verify & Save.
7. Retry the scheduling, rescheduling, or cancellation action.

After reconnecting the integration:

1. Confirm that the live chat workflow containing Get Scheduler via Calendly remains published and active.
2. Confirm that the Calendly event used by the workflow is available.
3. Run a test booking from the live chat widget.
4. Verify that BoldDesk creates the related ticket and records the meeting details.

If signature validation continues to fail, contact BoldDesk Support and provide:

• BoldDesk organization URL or organization ID.
• Calendly account or organization used by the integration.
• Related chat conversation ID.
• Related ticket ID, if available.
• Date, time, and time zone of the failed webhook.
• Exact error message.
• Screenshot of the Calendly app configuration without exposing API keys or credentials.

Contact BoldDesk Support

Contact BoldDesk Support if:

• A valid future time range continues to be rejected.
• A meeting is created in Calendly but no ticket is created in BoldDesk.
• Rescheduling or cancellation does not update the related ticket.
• Webhook signature validation continues to fail after reconnecting Calendly.
• The same error affects multiple customers or live chat conversations.

Provide:

• BoldDesk organization URL or organization ID.
• Exact error message.
• Screenshot of the error.
• Chat conversation ID.
• Calendly meeting or event link.
• Name of the BoldDesk live chat workflow.
• Date, time, and time zone of the event.
• Steps required to reproduce the issue.

Related Articles

1. How to Set up Calendly App with BoldDesk
2. How to Schedule Meetings in Live Chat Using Sticky Buttons
3. BoldDesk Third-Party Integrations: Access Marketplace and Apps