Schedule A Highfive Meeting: Outlook Calendar

If you're a Microsoft Outlook 2010-2016 user, the Highfive for Outlook Calendar Add-in makes scheduling Highfive calls in your calendar a one-click process.

Note: This feature is currently only available for Windows operating system users.


How to set up the Outlook Calendar Add-in:

  1. Download and install the Highfive application.
  2. Go to your Outlook Calendar.
  3. Under the Home tab, click on New Meeting.
  4. Click on the Highfive Login button. (Can't find this button? Click here for troubleshooting steps.)
  5. Your web browser will open and prompt you to sign into Highfive if you aren’t already logged in.
  6. Click Allow to use the Outlook Calendar Add-in.
  7. The Highfive button within your Outlook Calendar will now be labeled Add video call.
  8. Highfive! Your Outlook Calendar Add-in is ready to use.


Using the Highfive for Outlook Calendar Add-in:

  1. Create a meeting within your Outlook Calendar. For more information on how to do this, visit Microsoft’s Support Site here
  2. Once complete, click on the Highfive Add video call button.
  3. The subject name of your meeting will be used to automatically create a Highfive meeting link in the Location field. 
  4. For customers on Highfive service plans that include the phone dial-in feature, a dial-in link is also automatically added. For more information on how to dial-in, click here
  5. Highfive! At the time of the meeting, participants will only need to click the Join video call button to automatically launch the Highfive application and start their call.


Schedule a meeting from the Highfive application:

  1. You can also schedule a meeting in advance from the Highfive application by following these steps


Known issues:

Outlook 2010: If you're running Outlook 2010 and do not see the Highfive add-in, you'll need to install .NET framework (version 4.5 or above) and Visual Studios Tools for Office (VSTO) 2010 (x64). You can download the x64 version of VSTO 2010 at Microsoft's support site here.

Outlook 2016: If you're running Outlook 2016 and do not see the Highfive add-in, you'll need to install Visual Studios Tools for Office (VSTO) 2010 (x64). You can download the x64 version of VSTO 2010 at Microsoft's support site here.



  1. Some customers report being unable to see the Highfive add-in until they disable their Skype add-in and set the Highfive add-in to always be enabled. Microsoft's steps on how to manage these settings for Office 2016 can be found here
  2. If you have the Highfive application and then install Outlook afterwards, you’ll need to uninstall and reinstall the Highfive application for the Outlook Add-in to function.
  3. If you are on a Windows computer and are still not seeing the Highfive Add-in you may need to reinstall the VSTO file. Pick your user profile > appdata> local> Highfive > Outlook add-in and then double click on the VSTO to reinstall.  
  4. The Highfive add-in will not work with the in-browser web version of Outlook 365. Users will need to use the Outlook application. 
  5. Internet Explorer and Google Chrome users: If you don't have a browser window open before clicking on a Highfive meeting link within Outlook Calendar, you’ll be put into a Highfive application update loop. To fix this, open up a browser window first and then try clicking on the Highfive meeting link within your calendar afterwards. 
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