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AlisonC_ZA
Community Member
May 4, 2026
Question

Outlook Calendar Sync Issue

  • May 4, 2026
  • 6 replies
  • 194 views

Outlook is not syncing to my personal microsoft email account - i have already troubleshooted via the BOT and have been waiting ages for a human to connect with me to support resolving this issue.  Any tips beyond the obvious troubleshooting please - the connected calendar IS the right email account (I do have another email account which is a work account but that is not the calendar which is on the linked account under connections).  Any advice greatly appreciated

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6 replies

David
Community Manager
David
Community Manager
May 4, 2026

Hey ​@AlisonC_ZA - It looks like an Agent was helping you through installing the Outlook Plug-in - If you need additional resources you can find more on this here: https://calendly.com/help/outlook-plug-in-overview

Let me know if you have any questions, or reach back out via chat!

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AlisonC_ZAAuthor
Community Member
May 5, 2026

Hi David.  No luck - if I try to connect via Plug In the Setting “reread” does not save and it defaults back to empty.  We did a full control shift D removal of all Plug In Files and still no resolution.  If I try to link via .com then calendly picks up a calendar that is not the one I need it to reference - I think this is because of Office 365 Co-Pilot and the new outlook (I have chosen to use Outlook Classic in order to import my classic pst file from old laptop, but New Outlook Calendar is still on my laptop and I cannot remove it (have tried).  Co-Pilot is automatically loaded with any new Windows 11 Install.  I surely cant be the only person with this issue?  I have used Calendly successfully for nearly 6 years and only now that I have a new laptop with co-pilot installed do I have this issue.  I really need tech assistance - am waiting on an email as my last chat with the agent yesterday he was going to escalate for me.  We ran out of troubleshooting options.  

David
Community Manager
David
Community Manager
May 5, 2026

Hi ​@AlisonC_ZA - Understood, thanks for letting me know.

I’ll check in on your ticket today to see where its at, and see if we can expedite it. :)

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    AlisonC_ZAAuthor
    Community Member
    May 6, 2026

    Hi David - any progress on my ticket as yet?

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    AlisonC_ZAAuthor
    Community Member
    May 6, 2026

    I can see now that the calendar CALENDLY is linking to is definitely my microsoft 365 subscription account, which is linked to co-pilot.  I installed a separate version of outlook classic to enable me to migrate my outlook data from my old laptop to my new one (which has this automatic co-pilot loaded! 😔)

    Calendly seems to only “see” this account and does not register that my email address associated with my microsoft login has both new and classic versions of outlook.  The new is web based. I am continuing to troubleshoot but welcome any advice from anyone in a similar predicament. 

     

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    Ava16424
    New Community Member
    May 14, 2026

    Hey Alison! I had a similar headache with my Outlook sync recently.

    Usually, when the connection says it's right but nothing's showing up, it's a "token" issue basically, the secret handshake between Calendly and Microsoft has expired or gotten glitched.

    The quickest fix is to just disconnect and then reconnect your Microsoft account in your Calendar Connections. It forces them to re-verify everything from scratch, which usually clears up those weird sync gaps.

    Also, just a quick check are you using the Outlook Desktop app or the web version (Office 365)? Sometimes the sync behaves differently depending on the version. Hope that helps

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