Task Automation Rules

Eliminate repetitive work and ensure consistency with Waymaker's powerful automation system. Create intelligent rules that trigger actions based on task changes, saving hours of manual work and reducing errors.

Overview

Automation rules transform your taskboards from passive tracking tools into intelligent workflow engines. Instead of manually updating fields, assigning tasks, or sending notifications, define rules that execute automatically when specific conditions are met.

What Are Automation Rules?

An automation rule consists of three components:

Triggers: Events that activate the rule (task status changes, field updates, time-based conditions)

Conditions: Optional filters that must be true for the rule to execute (task priority is high, assignee is specific team member)

Actions: Operations performed when the rule triggers (move task, send notification, update fields)

Key Benefits

Time Savings Automate repetitive actions that would otherwise require manual intervention, freeing team members to focus on high-value work.

Consistency Ensure workflow steps execute reliably every time without depending on someone remembering to take action.

Error Reduction Eliminate mistakes from manual data entry or forgotten steps in multi-stage processes.

Process Enforcement Automatically enforce team processes and policies through automated checks and actions.

Scalability Handle growing task volumes without proportional increases in administrative overhead.

Automation Overview

Understanding the automation system's capabilities and limits helps you design effective rules.

Rule Types

Board-Level Rules Apply to all tasks within a specific board. Useful for board-specific workflows and processes.

Organization-Level Rules Apply across all boards in your organization. Best for company-wide standards and policies.

Task Template Rules Execute when tasks are created from specific templates, enabling template-specific automation.

Execution Model

Event-Driven Rules execute immediately when triggering events occur, typically within 1-2 seconds.

Sequential Processing Multiple rules can trigger from the same event. They execute in priority order with conflict resolution.

Atomic Operations Each rule execution is atomic—it either fully completes or fully fails without partial updates.

Performance Considerations

Rule Limits Organizations have limits on total active rules based on subscription plan:

Free: 5 active rules
Professional: 25 active rules
Business: 100 active rules
Enterprise: Unlimited rules

Execution Time Complex rules with many conditions or actions may take several seconds. Design rules to be as simple as possible.

Rate Limiting Rapidly triggering rules (thousands per minute) may be rate-limited to protect system performance.

Creating Automation Rules

Build your first automation rule with the visual rule builder.

Accessing the Rule Builder

Step 1: Open Automation Settings Navigate to board settings and select the "Automation" tab. Click "Create Rule" to open the rule builder.

Step 2: Choose a Template or Start Blank Select from pre-built templates for common workflows or choose "Blank Rule" for custom automation.

Step 3: Name Your Rule Give your rule a descriptive name that clearly indicates its purpose: "Auto-assign design tasks to Sarah" or "Notify team when high priority tasks are blocked."

Rule Builder Interface

Trigger Section Define what event activates the rule using the trigger dropdown and configuration options.

Condition Section Add optional filters that must be true for actions to execute. Multiple conditions combine with AND/OR logic.

Action Section Specify one or more actions to perform when the rule triggers and conditions are met.

Test Panel Test your rule against existing tasks before activating to verify it behaves as expected.

Saving and Activating Rules

Save as Draft Save incomplete rules as drafts to continue editing later without activating them.

Activate Immediately Save and activate the rule to begin automatic execution. The rule processes future events immediately.

Schedule Activation Schedule rule activation for a future date/time to align with process rollouts or sprint changes.

Triggers

Triggers define the events that activate automation rules.

Status Change Triggers

Any Status Change Trigger when task status changes to or from any value. Useful for universal status change actions like logging or notifications.

Specific Status Entered Trigger when a task enters a specific status:

"When status changes to In Progress"
"When status changes to Done"
"When status changes to Blocked"

Specific Status Exited Trigger when a task leaves a specific status:

"When status changes from To Do"
"When status changes from Review"

Status Transition Pairs Trigger only on specific status transitions:

"When status changes from In Progress to Done"
"When status changes from To Do to In Progress"

Assignment Triggers

Task Assigned Trigger when a task is assigned to any user or to a specific user:

"When task is assigned to anyone"
"When task is assigned to Sarah"
"When task is assigned to me"

Task Unassigned Trigger when assignee is removed from a task.

Assignee Changed Trigger when assignee changes from one user to another, optionally filtered to specific users:

"When assignee changes from anyone to James"
"When assignee changes from Sarah to anyone"

Due Date Triggers

Due Date Set Trigger when a due date is added to a task that previously had no due date.

Due Date Changed Trigger when an existing due date is modified to a different date/time.

Due Date Approaching Trigger when current time reaches a specific interval before the due date:

"When due date is 3 days away"
"When due date is 24 hours away"
"When due date is 1 week away"

Due Date Passed Trigger when a task becomes overdue:

"When due date passes and task is incomplete"
"1 day after due date passes"

Field Update Triggers

Any Field Changed Trigger when any field on the task is modified. Useful for general change logging.

Specific Field Changed Trigger when particular fields are updated:

"When priority changes"
"When layer changes"
"When estimate changes"
Custom fields

Field Value Set Trigger when a field is set to a specific value:

"When priority is set to High"
"When label contains 'Bug'"

Time-Based Triggers

Task Created Trigger immediately when a new task is created on the board.

Scheduled Time Trigger at a specific time each day, week, or month to run maintenance actions:

"Every day at 9 AM"
"Every Monday at 8 AM"
"First of every month"

Time Since Last Update Trigger when a task hasn't been updated for a specified duration:

"When task hasn't been updated for 7 days"
"When task has been in same status for 3 days"

Dependency Triggers

Dependency Completed Trigger when a task this task depends on is marked complete.

All Dependencies Completed Trigger when all tasks this task depends on are complete.

Blocked By Added Trigger when a dependency is added that blocks this task.

Comment and Activity Triggers

Comment Added Trigger when any comment or a comment containing specific keywords is added:

"When any comment is added"
"When comment contains '@approval-needed'"

Attachment Added Trigger when a file or link is attached to the task.

Checklist Completed Trigger when all checklist items in the task are marked complete.

Actions

Actions define what happens when a rule triggers and conditions are met.

Task Movement Actions

Move to Status Change the task's status to a specified value:

Move to "In Progress"
Move to "Done"
Move to "Blocked"

Move to Layer Change the task's layer assignment:

Move to "Sprint 2"
Move to "Backlog"
Move to specific milestone layer

Move to Board Transfer the task to a different board entirely, useful for escalation or handoff workflows.

Assignment Actions

Assign Task Assign the task to a specific user:

Assign to task creator
Assign to specific team member
Assign to the user who triggered the rule

Unassign Task Remove the current assignee, returning the task to unassigned state.

Add Follower Add specific users as task followers to receive notifications without being assignees.

Notification Actions

Send Notification Send in-app notification to specified users:

Notify assignee
Notify task creator
Notify specific team members
Notify all board members

Send Email Send email notification with customizable subject and body:

Email assignee
Email stakeholder list
Include task details and link

Send Slack Message Post message to Slack channel or direct message:

Post to #project-updates channel
DM the assignee
Include custom message template

Send Webhook Trigger webhook to external service with task data payload for custom integrations.

Field Update Actions

Set Priority Change task priority:

Set to High
Set to Low
Increase priority by one level

Set Due Date Set or modify the task's due date:

Set to specific date
Set to X days from now
Set to end of current sprint
Clear due date

Add Label Add one or more labels to the task:

Add "Urgent" label
Add multiple labels

Remove Label Remove specific labels from the task.

Update Custom Fields Set values for custom fields defined on the board.

Comment Actions

Add Comment Post an automated comment to the task:

Add status update comment
Add reminder or instruction
Include dynamic variables (assignee name, due date)

Add Checklist Automatically add a checklist with predefined items:

Add review checklist
Add quality assurance steps
Add handoff procedures

Dependency Actions

Create Subtask Automatically generate subtasks with predefined properties:

Create "Code review" subtask
Create "Testing" subtask
Set up multi-step workflow

Add Dependency Automatically link tasks based on rules:

Make this task depend on template task
Block subsequent tasks until this completes

Integration Actions

Create Calendar Event Generate calendar event for the task with specified settings.

Log to External System Send task data to external logging or analytics systems via API.

Update Related Record Update related records in integrated systems (CRM, support tickets, etc.).

Conditions and Filters

Conditions refine when actions execute by filtering which tasks are affected.

Basic Conditions

Task Property Conditions Filter based on task attributes:

Priority is High or Critical
Assignee is Sarah Jones
Layer is "Sprint 3"
Status is "In Progress"
Has due date
Has no assignee

Field Value Conditions Compare field values to specific values:

Estimate is greater than 8 hours
Due date is within next 7 days
Created date is today
Title contains specific keywords

Advanced Conditions

Multiple Condition Logic Combine conditions with AND/OR logic:

(Priority is High OR Priority is Critical) AND (Assignee is empty)
Status is "Blocked" AND (no update in last 3 days)

Negative Conditions Exclude tasks matching criteria:

Assignee is NOT Sarah
Status is NOT "Done"
Label does NOT contain "Archived"

Date-Based Conditions Sophisticated date filtering:

Due date is in the past
Created more than 30 days ago
Updated within last 24 hours
Due date is within current sprint

User Context Conditions

Current User Checks Conditions based on who triggered the rule:

Triggered by specific user
Triggered by task assignee
Triggered by board admin
Triggered by anyone except task creator

Hierarchy Conditions

Parent/Child Task Conditions Filter based on task relationships:

Is a subtask
Is a parent task
Has incomplete subtasks
All subtasks are complete

Dependency Conditions Filter based on task dependencies:

Has dependencies
Has no dependencies
All dependencies complete
Any dependency is blocked

Templates for Common Automations

Pre-built automation templates for frequent use cases.

Workflow Automation

Auto-Start Dependent Tasks "When all dependencies complete, move task to In Progress and assign to next team member"

Completion Workflow "When task moves to Done, unassign task, add completion comment, and notify stakeholders"

Escalation "When high priority task is in Progress for more than 3 days, notify manager and add 'Needs attention' label"

Assignment Automation

Round-Robin Assignment "When unassigned task enters To Do, assign to next available team member in rotation"

Skill-Based Assignment "When task with 'Frontend' label is created, assign to Sarah or James based on current workload"

Manager Review "When task is marked Done by team member, assign to manager for review"

Notification Automation

Overdue Alerts "When task becomes overdue, send daily email reminder to assignee and post to Slack channel"

Status Update Reminders "When task is In Progress for 2 days without update, notify assignee to add status comment"

Stakeholder Updates "When high priority task changes status, send email to stakeholder list with task summary"

Maintenance Automation

Stale Task Cleanup "When task hasn't been updated in 30 days and status is To Do, move to Backlog and add 'Stale' label"

Sprint Preparation "When sprint layer is created, automatically create standard sprint tasks (planning, review, retro)"

Archive Completed "When task has been Done for 14 days, move to Archived board"

Quality Assurance

Review Checklist "When task moves to Review status, automatically add review checklist items"

Testing Requirement "When high priority task moves to Done without test results attached, block completion and notify assignee"

Documentation Check "When task is marked Done and no documentation link exists, add 'Needs docs' label and return to In Progress"

Chaining Automations

Combine multiple rules for sophisticated workflows.

Sequential Automation

Multi-Stage Workflows Create sequences where one rule's action triggers the next rule:

Rule 1: "When task moves to Done → Move to Review and assign to QA team" Rule 2: "When task is assigned to QA team → Add testing checklist" Rule 3: "When testing checklist completes → Move to Done and notify stakeholders"

Conditional Branching

If-Then-Else Logic Use conditions to create different automation paths:

Rule A: "When task is Done AND estimate > 8 hours → Require manager approval" Rule B: "When task is Done AND estimate ≤ 8 hours → Auto-complete"

Parallel Automation

Multiple Simultaneous Actions Multiple rules can respond to the same trigger for parallel processing:

Trigger: Task moves to Blocked

Rule 1: Add "Needs attention" label
Rule 2: Notify assignee and manager
Rule 3: Create follow-up task to resolve blockage
Rule 4: Post to Slack #blockers channel

All execute simultaneously when the task is blocked.

Recursive Prevention

Avoiding Infinite Loops Be cautious when automation actions can trigger other automations:

❌ Bad: Rule that assigns task when assignee changes (infinite loop) ✅ Good: Rule that assigns task only when assignee is cleared (terminates)

Waymaker includes infinite loop detection but design rules carefully to avoid issues.

Testing Rules

Validate automation behavior before activating in production workflows.

Rule Testing Interface

Test Against Existing Tasks Select existing tasks and simulate the rule trigger to see what actions would execute without actually performing them.

Test Results Preview View detailed breakdown of:

Which conditions passed/failed
Which actions would execute
Expected outcomes for each action
Any warnings or potential issues

Testing Strategies

Start with Limited Scope Test rules on a small subset of tasks or a test board before rolling out to production data.

Verify All Condition Branches Test scenarios that match conditions and scenarios that don't to ensure correct filtering.

Check Edge Cases Test with:

Tasks with no assignee
Tasks with no due date
Completed tasks
Deleted or archived tasks

Dry Run Mode

Non-Destructive Testing Enable dry run mode to have the rule execute and log what it would do without actually performing actions. Monitor logs to verify behavior.

Troubleshooting

Diagnose and fix automation rule issues.

Rules Not Triggering

Verify Rule is Active Check automation settings to confirm the rule is enabled, not paused or in draft mode.

Check Trigger Configuration Ensure the trigger event you expect is actually occurring. Review automation logs to see if triggers are firing.

Review Conditions Use the rule tester to verify conditions pass for the affected tasks. A single failed condition prevents all actions.

Confirm Scope Verify the rule applies to the board or organization where you're testing. Board-level rules don't affect other boards.

Actions Not Executing

Permission Issues Verify the rule has permissions to perform actions:

Assign users (requires user management permissions)
Move to boards (requires access to target board)
Send notifications (requires notification permissions)

Invalid Action Configuration Check that action parameters are valid:

Assigned user still exists and is active
Target status exists on the board
Target layer exists
Email addresses are valid

Execution Errors Review automation logs for error messages indicating why actions failed.

Unexpected Behavior

Multiple Rules Conflicting Check if multiple rules respond to the same trigger and create conflicting actions:

Rule A assigns to Sarah
Rule B assigns to James
Result: Task rapidly reassigns

Resolve by adjusting conditions or rule priority.

Action Order Issues Some actions depend on others completing first. Ensure action order in the rule is logical.

Timing Issues Time-based triggers may not fire at exact millisecond precision. Build in appropriate tolerances.

Performance Problems

Complex Conditions Simplify overly complex condition logic that may slow rule execution.

Too Many Actions Rules with many actions (>10) may execute slowly. Consider splitting into multiple rules.

High Trigger Frequency Rules that trigger hundreds of times per minute may experience delays due to rate limiting.

Advanced Automation Features

Sophisticated capabilities for complex workflows.

Variable Substitution

Dynamic Action Content Use variables in action content for dynamic values:

{task.title} - Task name
{task.assignee} - Assignee name
{task.due_date} - Due date
{user.name} - Triggering user name
{current_date} - Today's date

Example: "Task {task.title} assigned to {user.name} on {current_date}"

Custom Webhook Payloads

Structured Data Transmission Define custom JSON payloads for webhook actions:

{
  "task_id": "{task.id}",
  "event": "status_changed",
  "new_status": "{task.status}",
  "timestamp": "{current_timestamp}"
}

Rule Priority

Execution Order Control Set rule priority to control execution order when multiple rules trigger:

Priority 1 rules execute first
Priority 10 rules execute last
Same priority rules execute in creation order

Rule Scheduling

Time Windows Configure rules to only execute during specific timeframes:

Business hours only (9 AM - 5 PM)
Weekdays only
Specific date ranges

Conditional Actions

If-Then Logic Within Rules Create multiple action sets with different conditions within a single rule:

If priority is High → Assign to senior team member
If priority is Low → Assign to junior team member

API Access to Automation

Programmatic automation control for advanced use cases.

API Endpoints

Create Rules Programmatically Use Waymaker API to create automation rules from external systems or scripts.

Trigger Rules Manually Force-trigger specific rules via API for testing or batch processing.

Query Rule Status Retrieve rule execution history and statistics via API.

Webhook Integration

External System Triggers Configure webhooks to trigger Waymaker automations from external events:

GitHub PR merged → Move related tasks to Done
Stripe payment received → Create onboarding tasks
Zendesk ticket created → Create support task

Best Practices

Maximize automation effectiveness with proven strategies.

Design Principles

Start Simple Begin with simple, single-action rules and add complexity gradually as you validate behavior.

Single Responsibility Each rule should have one clear purpose. Multiple simple rules are easier to manage than one complex rule.

Clear Naming Use descriptive rule names that explain trigger and action: "Notify manager when high priority task is blocked"

Document Complex Rules Add detailed descriptions to rules with complex logic explaining intent and behavior.

Maintenance

Regular Audits Review automation rules quarterly to:

Disable unused rules
Update rules for process changes
Optimize slow or problematic rules

Monitor Execution Review automation logs weekly to identify:

Rules that never trigger (may be unnecessary)
Rules that trigger very frequently (may need refinement)
Rules with frequent errors

Version Control When modifying important rules, note the changes in the rule description to track evolution over time.

Team Coordination

Communicate Changes Notify team members when creating or modifying automation that affects their work.

Shared Ownership Designate automation owners responsible for maintaining rule sets in their areas.

Training Ensure team members understand which processes are automated to avoid duplicate manual work.

Getting Started

Begin automating your taskboards today.

Step 1: Identify Repetitive Tasks Observe your workflow for 1-2 weeks and note actions you perform repeatedly.

Step 2: Choose Your First Automation Select one simple, high-value automation to start—status-based assignment or notification rules work well.

Step 3: Build and Test Use the rule builder to create your automation and test thoroughly on a test board or small task set.

Step 4: Monitor Results After activation, monitor for a few days to ensure the rule behaves as expected.

Step 5: Iterate and Expand Refine your first rule based on results, then gradually add more automations to optimize additional workflows.

Next Steps

AI Task Management - Combine automation with AI assistance
Calendar Integration - Automate calendar sync
Import & Export - Automate data migration workflows
Team Collaboration - Configure automated notifications