How to troubleshoot the Outlook plug-in

Updated Aug 19, 20264 min read
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Follow these steps to fix issues with the Outlook Plug-In for desktops when encountering unexpected behaviors.

Confirm you're troubleshooting the Outlook plug-in

Calendly offers both an Outlook plug-in and an Outlook add-in. Each integration has its own installation and troubleshooting steps.

  • Outlook plug-in: Syncs your Outlook desktop calendar with Calendly to keep your availability up to date. Continue with this article.
  • Outlook add-in: Lets you schedule Calendly meetings directly from Outlook. See Calendly Outlook add-in instead.

Troubleshooting the plug-in

Step 1 – Check your system requirements

Make sure you're using a PC running Windows XP or later with Outlook 2007 or later.

If you use Outlook.com, Office 365, or Exchange, we recommend connecting your Microsoft calendar directly instead of using the Outlook plug-in. For instructions, see Connect your calendar.

Step 2 – Check your plug-in connection

Go to your Calendar settings and make sure your Outlook calendar is connected through the Outlook plug-in.

If it isn't connected, see Install the Outlook plug-in for setup instructions.

Step 3 – Check your plug-in version and last sync date

Go to your Calendar settings and check your Outlook plug-in version and Last sync date.

  • If you're not using the latest version of the Outlook plug-in (Version 174), reinstall the plug-in by following the steps in Install the Outlook plug-in.
  • If the Last sync date hasn't updated recently, continue to the next troubleshooting steps.

Step 4 – Make sure you're only running one version of the Outlook plug-in

In order for the Outlook plug-in to properly sync with Calendly, you should only run one instance of the Outlook plug-in per Calendly user.

Step 5 – Check that your Outlook plug-in is your system tray icon

The Outlook plug-in will only sync when it is running in the background and your computer is connected to the internet. Any changes made while your computer is off and the plug-in is disconnected will only update once your device is back on. To check if your Outlook plug-in is running:

  1. Select the upwards-facing arrow in your Windows taskbar to Show hidden icons.
  2. From there, look for an item listed with the Calendly logo.
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  3. If you do not see an instance of the Outlook plug-in running in your taskbar, use your PC's search bar to search for, and open the Calendly Plugin for Outlook. 4618345788695
  4. If you do not see the Calendly Plugin for Outlook app within your search bar, the Outlook plug-in is not installed on your device. For more information on how to install the Outlook plug-in, check out How to install the Outlook plug-in.

Step 6 – Check your Outlook plug-in advanced settings

Set your sync to "Realtime" so Calendly can update your Outlook calendar right away. To set your Outlook plug-in sync to realtime:

  1. Open the Outlook plug-in via the taskbar in Windows (or by searching for the Calendly Plugin for Outlook in your Windows search).
  2. Select Settings
  3. Select Advanced in the bottom left corner of the Settings window.
  4. Select Realtime under Auto-Sync within the Advanced Settings window.
  5. Select OK to confirm your changes within the Advanced Settings window.
  6. Select Save to save changes made within your Outlook plug-in Settings.
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  1. Open the Outlook plug-in via the taskbar in Windows (or by searching for the Calendly Plugin for Outlook in your Windows search).
  2. Select Settings
  3. Select Advanced in the bottom left corner of the Settings window.
  4. Check Reread Outlook and Reread Calendly under the section titled Logging.
  5. Select OK to confirm your changes within the Advanced Settings window.
  6. Select Save to save changes made within your Outlook plug-in Settings.
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  1. Open the Outlook plug-in via the taskbar in Windows (or by searching for the Calendly Plugin for Outlook in your Windows search).
  2. Press CTRL+SHIFT+U to open the Special Settings Screen.
  3. Check Disable MAPI to the right of Disable MAPI DLL for Outlook.
  4. Select OK to confirm your changes within the Advanced Settings window.
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