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Hello everyone,

I am currently experiencing an issue with Calendly connected to my Exchange server.

  • Sometimes Calendly connects and works without any issues.

  • Other times, it becomes unavailable or shows an error asking me to contact support.

  • I have contacted Calendly support multiple times. They asked me to allow their IP addresses on my firewall, which I did, but the issue persists.

  • Support keeps telling me it is a problem with my Exchange server. However, if that were the case, why does it sometimes work fine and then randomly stop?

  • Unfortunately, Calendly support cannot provide logs or diagnostics to show where exactly the communication fails.

I am looking for help to properly troubleshoot and fix this problem.

Additional Information:

  • I am using [Exchange Server 2019- on-premises].

  • The Exchange server is accessible externally, and I confirmed that firewall rules allow Calendly IPs.

Questions:

  1. What could cause Calendly to work intermittently with Exchange?

  2. How can I better diagnose whether the issue is on the Exchange side or the Calendly side?

  3. Are there specific Exchange settings (like throttling or authentication token issues) that could cause this behavior?

  4. What logs or monitoring tools would you recommend to capture where the failure happens?

Thank you for your help!

Hi ​@Sale14517 - Appreciate the information here, thanks for reaching out!

Sorry to hear that you’ve been running into this, I’ve added answers to your questions below as well as some additional information:

  1. Most often we see this its either due to the network OR if you’re using 2FA within Exchange, causing token changes that cause the disconnect.
  2. We aren’t seeing any widespread Exchange issues, and there are users utilizing the Exchange connection currently, If we were seeing issues across the product we’d be able to dig into it more. It does look like Support sent over some logs that can be sent to your IT/Microsoft support who can look into it.
  3. Here are some of the main reasons we see exchange connections fail:
    1. Calendly does not support the ActiveSync protocol and requires our customers be using EWS in order to leverage our Exchange connection.
    2. If your server is behind a firewall AND only accessible via a VPN connection, the Calendly/Exchange connection will not work.
    3. Calendly does not support IMAP / POP Connections
  4. I don’t know of any specific tools that can be used outside of what built into Exchange. I’d recommend asking for examples from Support and match up times with what you’re seeing in Exchange.
     

To be frank. I don’t have as much insight into your account as support does, but they should be able to get you more examples on when we’re seeing disconnects, and match those up with your IT.

Let me know if you have any questions.

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