Hey there @ttsouchlos - thanks for your topic, and great questions, here! Firstly, check out our New User Guide - it’ll def prove helpful as you get used to the platform!

It sounds like you have shared your Google Calendars with your Outlook Calendar. Is that right? If so - here’s some information you might find helps you resolve this! (Personally, I suggest directly connecting your Google Calendars to your Calendly account - you can connect up to six calendars! - which is the simplest and most direct way to avoid this issue. That said, hopefully the below info will prove helpful!) 

Many organizations utilize shared calendars within their connected calendar platforms. More information from each platform:

• Google: Share your calendar with someone
• Office 365: Share your calendar in Outlook on the web

Firstly, you might simply have too many shared calendars! Click “show content” below to read more about this!

Generally speaking, Calendly can access shared calendars for which you have read/write access. These calendars would appear in the "Check for conflicts" and "Add to calendar" menus on the Calendar Sync page or in your Outlook plug-in. For example:

Google shared/sub-calendars

Within the Google calendar settings, if one of the following is selected:

• "See only free/busy (hide details)" or
• "See all event details"

You will be able to add the shared or sub-calendar to the Check for Conflicts calendar configuration, but will not be able to add the calendar as their Add to Calendar.

On the contrary, if one of the following is selected:

• "Make changes to events" or
• "Make changes and manage sharing"

You will be able to add the shared or sub-calendar to both the Check for Conflicts and Add to Calendar calendar configurations.

Microsoft shared calendars - Changing Privileges

1. Sharing Office 365 calendars with low level access, may not acquire enough permissions for Calendly to interact with that calendar.
2. As Calendly requires CRUD level calendar permissions, you can change your calendar properties to grant access.
3. Minimum level permissions required is Editor.

Subscribed Calendars

Many calendars that you may be subscribed to, such as calendars displaying national holidays, company holidays, etc, are shared (often public) calendars. Generally, Calendly is not able to check subscribed calendars for conflicts.

If you would like Calendly to consider you unavailable on a holiday, for example, you can copy/clone the event on the subscribed calendar onto your own calendar, then set the event to "Busy."

Here is an example of a cloned Thanksgiving Day event in Google Calendar with the status set to "Busy."

Check out these articles in our Help Center for more info: 

Getting Started with Office 365 or Outlook.com 

Working with multiple email accounts and calendars

Connecting your calendar