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I
InsightsIA
Community Member
December 3, 2025
Question

Outlook keeps disconnecting, part 2

  • December 3, 2025
  • 1 reply
  • 77 views

Sadly, this continues to occur randomly each week. 

It seems like MS continually changes the SID of my calendar so it continues to get disconnected.

I know this is also happening to other users as well, as they cancel the appointment I set using their Calendlys.

So I’m hoping someone can answer how to solve this once and for all? As a single MS365 user I have no sway with MS, so going that route is a non-starter.

Honestly, I’m at whit's end here, and while I love Calendly, I can’t have important customers booking meetings when I’m already busy with other important customers - the “my Calendy disconnect from Microsoft again” excuse has run it’s course :-(

Shawn

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    1 reply

    David
    Community Manager
    David
    Community Manager
    December 4, 2025

    Hi ​@InsightsIA - Thanks for reaching out, sorry to hear this is going on!

    So, there are a couple reasons why this might be happening so frequently:

    • Your Microsoft account password change.
    • You have Two-factor/MFA enabled or reconfigured.
    • Other security/policy updates that revoke tokens or require fresh consent. (Although this is more common for users in a larger Microsoft 365 organization)

    I’ve seen this happen most often with users who have MFA enabled within their account - Is that something you have configured?

    If none of these apply to you, the next thing I would do is check in with our support team. They’ll be able to take a closer look into whats going on, and what errors we’re seeing. You can either chat in, or email support@calendly.com to get in touch directly.

    Let me know if you have any questions!

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