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Calendly for Outlook: Plugin, Add-in & Workflows Guide

Fernando Figueiredo
March 11, 2025
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3
 min read
Contents

Effectively managing your meeting schedule can impact your productivity and your business’s. If you're using Calendly for appointment scheduling and Outlook as your email provider, connecting these tools simply creates a more efficient workflow. But you probably know this already. 

This guide will walk you through everything you need to know about the Calendly Outlook plugin and add-in, from installation to practical uses. We'll also introduce how Zeeg offers advanced scheduling at a lower price point, and with enhanced GDPR compliance.

Try Zeeg now

Does Calendly work with Outlook?

Yes, Calendly works with Outlook through several methods:

  1. Direct Office 365/Outlook.com calendar connection
  2. Outlook plugin for Windows desktop users
  3. Outlook add-in for scheduling directly from your inbox
  4. Outlook Workflows

The integration allows for bidirectional syncing, preventing double-booking and streamlining the scheduling process.

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Calendly for Outlook Plugin vs Outlook add-in vs Outlook workflows

Before diving into installation steps, it's important to understand the difference between these three type of connections between Outlook and Calendly.

Outlook plugin

The Outlook plugin serves as a behind-the-scenes connection between Calendly and your desktop Outlook calendar. Also referred to as the desktop plugin, this tool runs quietly in the background of your Windows computer, creating a link between your scheduling platform and your Outlook calendar. 

When active, it continuously monitors your Outlook schedule for potential conflicts, and automatically adds any new Calendly appointments to your calendar. 

It's worth noting that this plugin is exclusively available for Windows users with Outlook 2007 or later running on Windows XP or newer systems (doesn’t run on Mac). And for the plugin to work effectively, both your computer and the plugin must be running simultaneously.

Outlook add-in

Unlike the background-operating plugin, the Outlook add-in brings Calendly's functionality directly into your Outlook interface, giving your inbox scheduling capabilities. 

With the add-in, you can instantly access and share your Calendly links while reading or composing emails, eliminating the need to switch between applications. The tool also provides a centralized hub for viewing upcoming meetings, tracking your contact history, and booking appointments in real-time. 

Also, this connection lets you create specialized scheduling options like one-time meetings, single-use links, and group meeting polls – all without leaving Outlook email.

Outlook Workflows for Calendly

This extension allows you to automate your email communications through your Outlook account rather than using Calendly's default email system. When you set up these workflows, all automated emails (such as appointment confirmations, reminders, follow-ups, and cancellation notices) are sent directly from your personal Outlook email address instead of appearing as "notifications@calendly.com."

Your recipients see your actual email address as the sender, making communications feel more personal and professional, and being able to reply; and all sent workflow emails appear in your Outlook "Sent" folder, keeping your communication history organized in one place, with consistency.

How to install the Calendly Outlook add-in

The installation process varies slightly depending on your version of Outlook:

For Office 365 or Outlook for Mac

  1. Access the Calendly for Outlook add-in through the Microsoft AppSource store
  2. Click "Get it now"
  3. Sign in to Microsoft AppSource with your email address as requested
  4. Follow the prompts to complete installation

For Outlook for Windows, Outlook 2019, or Outlook 2016

  1. In Outlook, go to the navigation bar
  2. Select "More Apps" > "Add apps"
  3. Search for "Calendly for Outlook"
  4. Select "Add"

Note: If you have an older version of the add-in already installed, you'll need to log in to your Microsoft account and uninstall it before installing the newest version.

How to access the Calendly Outlook add-in

Once installed, accessing the add-in is straightforward:

  1. In Outlook, select "Compose" to create a new email
  2. Find and select the Calendly icon in the Outlook toolbar
  3. Log in to your Calendly account
  4. Your event types will appear on the right-hand side of the window

How to install the Calendly Outlook plugin

The Outlook plugin is specifically designed for Windows users who cannot use the Office 365/Outlook.com connection. To install:

  1. Contact Calendly support to receive a download link (you must be logged into Calendly to access it)
  2. Download and save the plugin file
  3. Run the installation (allow any security permissions that pop up)
  4. Enter the unique key Calendly generates for you
  5. Select which calendar accounts to check for conflicts
  6. Choose the calendar where you want new meetings to be added
  7. Save your changes
  8. Click "Sync Now" to begin syncing between Outlook and Calendly

Important requirements for the Outlook plugin

For the plugin to work properly:

  • Both Outlook and the plugin must either run in administrator mode or not run in administrator mode
  • Configure Outlook to always use the same profile
  • Leave plugin settings in their default state unless you have a specific reason to change them
  • If you have a firewall, ensure that calendly.exe is added to the allowlist
  • The plugin is not compatible with Outlook versions downloaded from the Microsoft/Windows store

Another way to setup Calendly with Outlook (three options)

If you're using Office 365 or Outlook.com, you have another option for connecting your calendar to Calendly:

  1. Go to your Calendly Dashboard
  2. Select "Integrations" and type in "Outlook" on the search bar
  3. Choose one of the three integrations you want: Outlook Calendar (plugin), Calendly for Outlook (add-in), and Outlook for Workflows
  4. Sign in to your Microsoft account when prompted
  5. Follow the instructions that will be prompted depending on your choice:
  • if you choose the first, Outlook Calendar (plugin), then pick which calendars Calendly should check for conflicts, set which statuses (Busy, Working Elsewhere, Away, etc.) should make you unavailable, which calendars Calendly should add new events to, and enable "Sync Cancellations" (optional)
  • if you choose Calendly for Outlook (add-in), you'll be taken again to the AppSource Store, so you just need to get the extension and follow the instructions
  • if you choose Outlook for Workflows, you'll have to press "Connect Microsoft Outlook" on the new window, and follow the quick set-up instructions

How Calendly reads your Outlook calendar status

Understanding how Calendly interprets your Outlook calendar statuses is crucial for effective scheduling. The platform recognizes the various availability markers you set in Outlook and translates them into your Calendly availability. 

By default, Calendly considers any time blocks marked as "Busy," "Working Elsewhere," or "Away/Out of office" as unavailable periods, automatically removing these slots from your scheduling page. Conversely, events labeled as "Free" or "Tentative" remain open for booking, allowing potential meetings during these more flexible times. 

If this default behavior doesn't align with your scheduling preferences, you can easily adjust these settings through your Calendar settings page. This customization gives you better control over how your Outlook calendar status influences your Calendly availability, ensuring your scheduling accurately reflects your true availability across both platforms.

Alternatives to Calendly Outlook integration

While Calendly's Outlook integration works well for many users, several alternatives are worth considering, based on your needs and circumstances.

Zeeg: Zeeg offers a budget-friendly alternative to Calendly with comparable functionality at a lower price point. This scheduling platform provides advanced features like smart routing forms that qualify leads and round-robin scheduling for teams. As a European-developed solution, Zeeg delivers full GDPR compliance with secure data hosting in EU-based servers, making it ideal for privacy-conscious businesses. The platform connects seamlessly with various calendar systems beyond Outlook, including Google Calendar and Apple Calendar, giving you flexibility across different tools. With customizable booking pages and automated workflows for reminders and follow-ups, Zeeg provides a comprehensive scheduling solution with plans starting at just $7/month.

Microsoft Bookings: For organizations already invested in the Microsoft ecosystem, knowing how to use Microsoft Bookings might just be what you need. It's the natural (and native) integration option. It comes included with many Microsoft 365 Business and Enterprise subscriptions, eliminating the need for additional software expenses. Bookings offers direct integration with Outlook calendars, Teams meetings, and the broader Microsoft environment. The platform features a customer-facing booking page, automated confirmation emails, and staff scheduling capabilities. While not as feature-rich as dedicated scheduling platforms, Microsoft Bookings provides a straightforward solution for basic appointment scheduling needs within the familiar Microsoft interface.

CRM scheduling tools: If you already use a CRM system like HubSpot or Pipedrive, their built-in scheduling features might eliminate the need for a separate tool entirely. These integrated schedulers allow you to merge your email communications, customer relationship management, and appointment scheduling in one centralized platform. HubSpot's Meeting Scheduler and Pipedrive's Scheduler both connect with your Outlook calendar while keeping all customer interaction data within your CRM. This unified approach provides valuable context for meetings and streamlines workflows by reducing the number of platforms you need to manage. However, these tools typically offer fewer specialized scheduling features compared to dedicated solutions, focusing instead on integration with your sales and marketing processes.

👉 Read more:

Zeeg: Integrate with Outlook, save money, and get more leads

While Calendly offers functionality for Outlook users, Zeeg provides a compelling alternative with enhanced features:

Zeeg delivers the same core functionality as Calendly's Outlook integrations while offering additional benefits for businesses concerned with data protection and advanced scheduling needs.

Try Zeeg now

Troubleshooting common issues

For the Outlook plugin

When encountering issues with the Calendly Outlook plugin, several fixes can resolve most problems. First, verify that both your computer and the plugin are actively running, as the synchronization depends on that. Next, check that your administrator settings are consistent across both Outlook and the plugin—they must either both run in administrator mode or both run in standard mode to communicate properly.

Another common source of trouble stems from using incompatible software versions. Ensure you're using an Outlook version downloaded directly from your Office 365 account rather than the Microsoft Store, as store versions aren't compatible with the plugin. If you've recently updated Office and started experiencing problems, upgrading to the latest version might resolve compatibility issues introduced by the update. As a final troubleshooting step, sometimes the simplest solution works best—restart your computer to refresh all systems and potentially clear any temporary glitches affecting the synchronization.

For the Outlook add-in

Issues with the Outlook add-in typically have different solutions than plugin problems. When the add-in fails to appear in your Outlook interface, first try restarting the application completely to trigger a fresh load of all components. If that doesn't work, the problem may involve permissions—check with your organization's administrator to confirm you have the necessary rights to use add-ins in your Outlook environment.

For persistent problems, uninstalling and reinstalling the add-in often resolves underlying configuration issues that aren't immediately apparent. This process essentially gives you a clean slate, removing any corrupted files or settings. Finally, verify you're logged into the correct Calendly account within the add-in, as authentication issues can prevent proper functioning even when the add-in itself is correctly installed. Most users find that one of these approaches effectively restores normal operation of their Calendly integration.

Final thoughts

Integrating Calendly with Outlook can indeed streamline your scheduling workflow, reducing the back-and-forth that comes with setting up meetings. Whether you choose the plugin for calendar syncing, the add-in for in-inbox scheduling, or a direct Office 365 connection, you'll gain time and get rid of scheduling headaches.

But for those looking for an alternative solution that is more affordable, safe and compliant, and that also works with Apple Calendar, Zeeg offers comparable functionality with enhanced privacy features and a user-friendly interface.

Try Zeeg now