Calendar Integration

Keep your taskboards and calendar in perfect sync. Automatically create calendar events for tasks, sync due dates bidirectionally, and manage your schedule across Waymaker and your preferred calendar application.

Overview

Calendar integration bridges the gap between task management and time management. Tasks with due dates automatically appear on your calendar, calendar events can create tasks, and changes sync in both directions to maintain a single source of truth for your schedule.

Key Benefits

Unified Schedule Visibility See all your commitments—tasks, meetings, and events—in one place without manually duplicating information across systems.

Automatic Event Creation Tasks with due dates automatically create calendar events, eliminating manual calendar entry and ensuring your schedule reflects your taskboard commitments.

Bidirectional Sync Changes made in either Waymaker or your calendar sync automatically, so you can work in whichever tool fits your current context.

Time Blocking Reserve calendar time for task completion with automatic blocking based on task estimates and deadlines.

Supported Calendar Services

Waymaker integrates with all major calendar platforms through native connections.

Google Calendar

Full Integration Support

Two-way sync between Waymaker and Google Calendar
Multiple calendar support (work, personal, project-specific)
Shared calendar integration for team visibility
Recurring event patterns
Event attendee synchronization
Color coding based on task properties

Connection Method OAuth authentication provides secure, permission-based access to your Google Calendar. You authorize specific calendar access without sharing credentials.

Microsoft Outlook

Office 365 and Exchange

Full compatibility with Office 365 calendars
Exchange server support for enterprise environments
Teams meeting integration
Shared mailbox calendar access
Outlook categories sync with task labels

Enterprise Features

SSO integration for organizations using Microsoft as identity provider
Conditional access policy compliance
Advanced security and compliance features

Apple Calendar (iCloud)

iCloud Calendar Integration

Two-way sync with iCloud calendars
Cross-device synchronization (Mac, iPhone, iPad)
Calendar sharing capabilities
iCloud Calendar events can create Waymaker tasks

Native App Support Synced events appear in Apple Calendar app across all your devices with no additional configuration.

Generic CalDAV

Universal Calendar Protocol Connect any CalDAV-compatible calendar service including:

Fastmail
Nextcloud
Zimbra
Self-hosted calendar servers

CalDAV provides open-standard calendar access for maximum compatibility.

Connecting Your Calendar

Set up calendar integration in minutes with straightforward authentication flows.

Initial Connection

Step 1: Open Integration Settings Navigate to your account settings and select "Integrations" from the sidebar menu.

Step 2: Select Calendar Service Choose your calendar provider from the available options: Google Calendar, Microsoft Outlook, Apple Calendar, or CalDAV.

Step 3: Authorize Access Click "Connect" to initiate the OAuth authorization flow. You'll be redirected to your calendar provider to grant permissions.

Step 4: Grant Permissions Review and approve the requested permissions:

Read calendar events
Create and modify events
Delete events created by Waymaker
Access calendar settings

Step 5: Configure Sync Settings After authorization, configure initial sync preferences:

Which calendars to sync
Default calendar for new tasks
Sync direction preferences
Update frequency

Selecting Calendars

Multiple Calendar Support If you have multiple calendars, choose which ones integrate with Waymaker:

Primary Task Calendar Select one calendar as the default destination for task-related events. This calendar receives events for all tasks with due dates unless specified otherwise.

Project-Specific Calendars Map different Waymaker boards or projects to different calendars for organizational clarity:

Product Development board → Product Calendar
Marketing Campaigns board → Marketing Calendar
Personal Tasks board → Personal Calendar

Shared Team Calendars Integrate shared team calendars to provide visibility into task deadlines for all team members without requiring everyone to use Waymaker.

Disconnecting and Reconnecting

Temporary Disconnection Pause sync without removing integration settings using the "Pause Sync" toggle in integration settings. Useful for troubleshooting or temporary privacy needs.

Full Disconnection Remove the integration entirely through "Disconnect Calendar." This revokes Waymaker's access and removes sync settings, but preserves existing calendar events previously created by Waymaker.

Reconnection Reconnecting requires re-authorization but can restore previous sync settings if disconnect was recent.

Two-Way Sync Capabilities

Understanding bidirectional synchronization helps you work confidently across both systems.

Waymaker to Calendar

Automatic Event Creation When you set or update a task's due date in Waymaker, the integration automatically:

Creates a calendar event at the due date/time
Titles the event with the task name
Includes the task description in event notes
Adds a link back to the Waymaker task
Sets event duration based on task estimate

Update Propagation Changes to task properties sync to the calendar event:

Due date changes update event time
Task title changes update event title
Priority changes update event color
Task completion removes or marks the event

Calendar to Waymaker

Event-Created Tasks Create tasks directly from your calendar by adding events with specific keywords or hashtags:

Events containing "#task" automatically create Waymaker tasks
Event title becomes task title
Event time becomes task due date
Event description populates task description

Event Update Sync Modifications to calendar events created by Waymaker sync back:

Reschedule the event → task due date updates
Change event title → task title updates
Mark event complete → task status updates

Conflict Resolution

Handling Simultaneous Changes When changes occur in both systems simultaneously, the integration uses configurable conflict resolution:

Last Write Wins (Default) The most recent change takes precedence, overwriting the older change.

Calendar Priority Calendar changes always override Waymaker changes. Useful if you primarily manage time in your calendar.

Waymaker Priority Waymaker changes override calendar changes. Appropriate if taskboards are your primary planning tool.

Manual Resolution For critical tasks, enable manual conflict resolution to review and choose the correct value when conflicts occur.

Task-to-Event Mapping

Control how task properties translate to calendar events.

Event Timing

Due Date Events By default, tasks create all-day events on their due date. This appears as a banner event spanning the full day in your calendar.

Scheduled Time Blocks Enable time blocking to create events at specific times rather than all-day entries:

Task estimated duration determines event length
Tasks auto-schedule in available calendar slots
Respect working hours and existing commitments

Lead Time Events Create events before the actual due date as reminders or work time:

"Start working 3 days before due date"
"Review 1 week before deadline"
Configurable per task or as board default

Event Duration

Estimate-Based Duration If tasks have time estimates, events use that duration:

2-hour task estimate → 2-hour calendar event
Overruns can automatically extend the event

Default Duration For tasks without estimates, use a configured default:

1 hour for standard tasks
30 minutes for quick tasks
4 hours for complex tasks
Customizable per board or task type

Event Details

Task Information in Events Calendar event descriptions include rich task information:

Full task description with formatting preserved
Assignee information
Priority and status
Link to open the task in Waymaker
Layer and project context
Recent activity summary

Attachments Task attachments can optionally link from calendar events for quick access to relevant documents during scheduled work time.

Event Categories and Colors

Color Coding Map task properties to calendar event colors for visual organization:

High priority tasks → Red events
Design tasks → Purple events
Completed tasks → Green events
Blocked tasks → Gray events

Calendar Categories Task labels or layers can map to calendar categories/tags for filtering and organization within your calendar application.

Sync Settings and Preferences

Fine-tune integration behavior to match your workflow.

Sync Frequency

Real-Time Sync Changes propagate within seconds for immediate consistency. Best for teams with high task activity and calendar dependency.

Scheduled Sync Synchronize on a schedule (every 15 minutes, hourly, daily) to reduce API usage and battery consumption on mobile devices.

Manual Sync Disable automatic sync and trigger synchronization manually when you want updates to propagate. Useful for careful review before changes appear in calendars.

Sync Direction

Bidirectional (Default) Changes flow in both directions between Waymaker and calendar for complete synchronization.

Waymaker to Calendar Only Tasks create and update calendar events, but calendar changes don't affect tasks. Use when calendar is a read-only view of commitments.

Calendar to Waymaker Only Calendar events create and update tasks, but task changes don't modify events. Useful when calendar is the authoritative schedule.

Filtering What Syncs

Task Criteria Define which tasks create calendar events:

Only tasks with due dates
Only high and medium priority tasks
Only tasks assigned to you
Only incomplete tasks
Custom filters based on labels, layers, or status

Date Range Limits Sync only tasks within specific timeframes:

Next 30 days only
Current and next sprint only
Within the next quarter
Prevents calendar clutter from distant deadlines

Notification Settings

Calendar Notifications Control whether calendar events created from tasks inherit your calendar's default notification settings or use Waymaker-specific notifications.

Waymaker Notifications Choose whether changes from calendar sync trigger Waymaker notifications:

Notify when calendar event creates a task
Notify when calendar reschedule changes due date
Notify when calendar deletion marks task complete

Timezone Handling

Ensure consistent timing across different timezones in distributed teams.

Timezone Defaults

User Timezone All times display and sync in your configured user timezone. Tasks created at "3 PM" appear at 3 PM in your timezone on your calendar.

Board Timezone Optionally set a board-level timezone for project-based scheduling:

Client projects use client timezone
Event coordination uses event location timezone
Global teams can standardize on UTC or headquarters timezone

Cross-Timezone Collaboration

Distributed Teams When team members work in different timezones:

Due dates use creator's timezone by default
Assignees see times converted to their timezone
Calendar events adjust automatically to viewer's timezone
Absolute times (UTC) stored prevent ambiguity

Daylight Saving Time

Automatic Adjustment The integration handles DST transitions automatically:

Events maintain the intended local time across DST boundaries
Recalculates when timezones shift
Preserves user intent (9 AM meeting stays 9 AM after DST)

Calendar Notifications

Manage how and when you receive calendar-based task reminders.

Default Reminders

Inherit Calendar Settings Use your calendar's default reminder settings for task events:

Google Calendar: 10 minutes before
Outlook: 15 minutes before
Customizable per calendar

Task-Specific Reminders

Override Defaults Set custom reminders for specific tasks:

Critical tasks: 1 day, 1 hour, and 15 minutes before
Routine tasks: 10 minutes before
Long-lead tasks: 1 week and 1 day before

Reminder Types

Notification Methods Calendar applications typically support multiple reminder types:

Pop-up notifications on desktop and mobile
Email reminders sent to your inbox
SMS reminders (if configured in calendar)

All configured reminder methods work with task-created events.

Smart Reminders

Context-Aware Timing Enable intelligent reminder timing based on task properties:

High priority tasks get earlier reminders
Tasks with dependencies remind you to check prerequisites
Recurring tasks use optimized reminder schedules

Troubleshooting Sync Issues

Resolve common calendar integration problems.

Events Not Appearing in Calendar

Verify Sync Settings Confirm that calendar sync is enabled and the task meets sync criteria (has due date, passes filters, etc.).

Check Calendar Selection Verify the correct calendar is selected as the sync destination and that calendar is visible in your calendar application.

Refresh Calendar Some calendar applications cache data. Manually refresh your calendar view to see recently created events.

Authorization Status Ensure the calendar connection remains authorized. Expired tokens or revoked permissions prevent sync.

Tasks Not Updating from Calendar

Sync Direction Verify bidirectional sync or calendar-to-Waymaker sync is enabled in integration settings.

Event Ownership Only events created by Waymaker or explicitly tagged for sync (#task) update Waymaker tasks. Manual calendar events don't create tasks unless tagged.

Field Mapping Check that the event properties you changed map to task fields. Some event properties may not have corresponding task fields.

Duplicate Events

Multiple Calendar Sources If you have multiple calendar integrations or subscription calendars, you may see duplicates. Disable redundant connections.

Re-sync Issues Disconnect and reconnect the calendar integration, then use the "Remove Duplicate Events" tool in integration settings.

Sync Delays

Check Sync Frequency If using scheduled sync rather than real-time, delays are expected based on your chosen interval.

Service Status Verify that your calendar provider's service is operational. API outages prevent synchronization.

Rate Limiting Excessive sync activity may trigger rate limiting. Adjust sync frequency or filter criteria to reduce API calls.

Missing Event Details

Permission Issues Ensure Waymaker has permission to read full event details, not just free/busy information.

Privacy Settings Some calendar privacy settings may hide event details. Adjust calendar sharing settings if working with team calendars.

Advanced Features

Sophisticated capabilities for power users.

Recurring Task Sync

Repeating Events Tasks with recurrence patterns create recurring calendar events:

Daily standups appear every day
Weekly reviews appear every Monday
Monthly planning appears on the first of each month

Pattern Customization Define complex recurrence rules:

Every weekday (Mon-Fri)
First and third Tuesday of each month
Every 2 weeks on Wednesday
Custom RRULE patterns

Meeting Integration

Calendar Events as Tasks Automatically create tasks for meetings that require preparation or follow-up:

"Prepare for Client Review" task created 1 day before meeting
"Send Meeting Notes" task created after meeting ends
Attendees become task collaborators

Resource Scheduling

Room and Resource Calendars Integrate resource calendars (conference rooms, equipment) to:

Reserve resources when tasks require them
Check resource availability before scheduling
Automatically release resources when tasks complete

Multiple Calendar Views

Calendar Overlays Display multiple Waymaker boards on different calendars:

Personal calendar for your assigned tasks
Team calendar for all team tasks
Project calendar for specific board tasks
Master calendar combining all sources

Integration Examples

Real-world scenarios demonstrating effective calendar integration.

Agile Sprint Planning

Scenario: Two-week sprint with defined commitments and ceremonies.

Setup:

Sync sprint board to team calendar
Sprint tasks create time blocks during working hours
Ceremonies (planning, standup, retro) manually added to calendar
Task deadlines visible alongside meetings

Result: Team members see sprint commitments alongside meeting schedules, can plan focused work time, and identify scheduling conflicts early.

Client Project Management

Scenario: Multiple client projects with different timelines and stakeholder meetings.

Setup:

Each client board syncs to a client-specific calendar
Client meetings in calendar create preparation tasks in Waymaker
Deliverable tasks appear on client calendar for visibility
Share client calendar with stakeholders for transparency

Result: Clients see project milestones on shared calendar while team manages detailed tasks in Waymaker with automatic synchronization.

Personal Productivity

Scenario: Individual managing work tasks, personal commitments, and side projects.

Setup:

Work tasks sync to work calendar
Personal tasks sync to personal calendar
Side project board syncs to separate project calendar
All calendars visible in unified calendar view

Result: Complete schedule visibility across all life areas with separation maintained for different contexts.

Event Planning

Scenario: Planning a conference with many deadlines and coordinated timing.

Setup:

Event taskboard syncs to shared team calendar
Key milestone tasks create all-day calendar events
Vendor meeting calendar events create follow-up tasks
Timeline visualization in calendar format

Result: Team coordinates complex event planning with clear visibility into deadlines and dependencies via familiar calendar interface.

Best Practices

Maximize calendar integration value with proven strategies.

Intentional Sync Scope

Selective Syncing Don't sync everything—choose tasks that benefit from calendar visibility:

Time-sensitive tasks with specific deadlines
Tasks requiring scheduled focus time
Cross-team commitments needing visibility
Exclude: small tasks, distant deadlines, low-priority items

Consistent Timezone Usage

Standardize for Teams Establish timezone conventions for your team:

Use project timezone for client work
Use UTC for global coordination
Document timezone expectations for remote teams

Regular Review and Cleanup

Weekly Calendar Audit Review your calendar weekly to:

Remove completed task events if they linger
Reschedule tasks with changed priorities
Verify sync accuracy and resolve conflicts
Archive old events and completed projects

Clear Naming Conventions

Distinguishable Events Use task naming that's clear in calendar context:

Include project/board name in task title
Use consistent prefixes ([CLIENT], [INTERNAL], [PERSONAL])
Avoid overly short or cryptic task names

Privacy and Security

Understand how calendar integration protects your data.

OAuth Security

No Password Sharing Calendar integration uses OAuth 2.0 authentication—you authorize access without sharing your calendar password with Waymaker.

Revocable Access You can revoke Waymaker's calendar access at any time through your calendar provider's security settings.

Data Handling

Minimal Data Storage Waymaker stores only the calendar event IDs and sync metadata necessary for integration. Full event data remains in your calendar service.

Encryption All data transmitted between Waymaker and calendar services uses TLS encryption in transit.

Shared Calendar Considerations

Visibility When syncing to shared calendars, remember that all calendar users see synced task information. Don't sync sensitive tasks to shared calendars.

Edit Permissions Only users with edit access to the calendar can modify events. This may differ from Waymaker task permissions.

Getting Started

Begin using calendar integration today.

Step 1: Connect Your Calendar Go to Settings → Integrations → Calendar and connect your preferred calendar service.

Step 2: Configure Sync Preferences Choose which boards or task types should sync to your calendar.

Step 3: Test with a Few Tasks Create a few test tasks with due dates and verify they appear correctly in your calendar.

Step 4: Verify Bidirectional Sync Modify an event time in your calendar and confirm the task due date updates in Waymaker.

Step 5: Expand Usage Once comfortable with the basics, enable calendar integration across all your active boards.

Next Steps

Task Automation - Automate calendar-related workflows
AI Task Management - Use AI to schedule and prioritize tasks
Import & Export - Migrate tasks and calendar events
Team Collaboration - Coordinate schedules with your team