TL;DR: Outlook Calendar Integration Plus offers 15 automation recipes as an alternative to the 2-way sync sidebar. Automations give you granular control over when and how events are created — triggered by column changes, button clicks, or new calendar events. They are essentially one-way: monday.com → Outlook or Outlook → monday.com.
Before you start
The 2-way sync sidebar is the primary and recommended way to keep monday.com and Outlook Calendar in sync. See Set up your first sync .
Automations are a secondary option, mainly used by users who are already familiar with monday.com's automation templates. Compared to the full sync configuration, automations offer fewer options and less control.
Automations are essentially one-way . Each recipe goes in one direction: monday.com → Outlook, or Outlook → monday.com.
Every automation run counts as 1 action toward your monthly quota.
How automations work
Automations in monday.com follow a simple structure: "When something happens → perform an action."
Trigger — the event that activates the automation (e.g., a column changes, a button is clicked, a new calendar event is created)
Action — what happens next (e.g., create an event in Outlook, create an item in monday.com)
When an automation runs, it checks the Integration Column:
If there's no connected event , it creates a new event
If there's an existing connected event , it updates or replaces it based on the update logic you choose
Update logic
When creating a monday.com → Outlook automation, you choose how updates are handled:
Update connected event — updates the existing event based on your field mapping. This is the default and recommended option for most use cases.
Create new event & keep previous event — creates a new event without deleting the old one. Useful when an item has rolling events (e.g., a sales lead with multiple meeting dates).
Create new event & delete previous event — replaces the old event entirely. Useful when you want to "reset" the event from scratch based on the current field mapping.
These automations create an item or subitem in monday.com when a new event appears in your calendar.
Create items:
When an account event is created in this calendar , create an item in this group .
When an account event is created in this calendar and only if its creator is someone , create an item in this group .
When an account event is created in this calendar and only if its title is this title , create an item in this group .
Create subitems:
When an account event is created in this calendar , create a subitem in this item .
When an account event is created in this calendar and only if its creator is someone , create a subitem in this item .
When an account event is created in this calendar and only if its title is this title , create a subitem in this item .
Deletion
These automations clean up calendar events when items or subitems are removed.
When an item is deleted, delete the connected calendar event.
When a subitem is deleted, delete the connected calendar event.
Setting up an automation
Open your board and click the Automate button (top-right, lightning icon).
Search for "Outlook Calendar" in the automation center.
Click Use template on the recipe you want.
Configure the placeholders — select your Outlook account, choose a calendar, map your fields, and set the update logic.
Click Create automation to activate.
During setup, you'll configure your Field Mapping — this determines how monday.com columns map to Outlook event fields.
Good to know
The 2-way sync sidebar and automations can work on the same board, but be careful not to create conflicting rules (e.g., a sync that creates events + an automation that also creates events for the same items).
Each automation run counts as 1 action. If you have 5 automations on one board and all 5 trigger from the same change, that's 5 actions.
Automations use the same Integration Column as the 2-way sync to track connections between items and events.
Conditional triggers in automations (status changes to "something", creator is "someone", title is "this title") work differently from the Conditional Triggering feature in the sync sidebar.