topic Re: Round Robin Calendar Issues - "Well This Is Disappointing" in Sales Hub Tools

Round Robin Calendar Issues - "Well This Is Disappointing"

LStier — Wed, 25 Jun 2025 17:58:38 GMT

We have a round robin calendar five users have used successfully to balance meetings for >1 year. Yesterday, the calendar broke - you can pick a day/time, fill out the form, but upon form submission it takes you to an error page with the "Well This Is Disappointing" messaging, asking you to reach out to the calendar owner.

No other meeting pages are experiencing issues. I've tried disconnecting and reconnecting all users emails. I've taken them out, and added them back. I created a new Round Robin meeting which experienced the same issue. I've contacted support. I've tried testing the meeting with each user individually and in different small groups. I tried another browser.

Is anyone else experiencing Round Robin issues or have any other troubleshooting ideas?

Re: Round Robin Calendar Issues - "Well This Is Disappointing"

JessicaBaskey — Thu, 26 Jun 2025 03:09:08 GMT

Hi @LStier,

A few of my clients ran into something similar this week: form submits fine, then redirects to that "Well This Is Disappointing" error message. In one case, it turned out to be an issue with the calendar connection timing out in the background — even though it looked connected. Disconnecting and reconnecting helped only after clearing cookies and reauthorising everything from scratch (not just via the HubSpot settings panel).

A few things that might help:

Double check that every user in the Round Robin has a connected calendar that’s syncing correctly (even one inactive or misconfigured user can break the flow).
Try switching off “Respect User Availability” temporarily to see if that changes the behaviour — sounds odd, but this helped isolate the issue for another team I worked with.
Look in Developer Tools (Network tab) while submitting the form to see what’s failing — might surface something support hasn’t caught yet.
If you’re using embedded forms or custom domains, make sure there aren’t any cookie/tracking issues breaking cross-domain tracking or submissions.

It’s good that support’s involved — this might be one of those sneaky backend bugs that require their dev team to resolve. In the meantime, you could clone the meeting link and assign it to only one user temporarily, just so meetings can still come through while it’s being sorted.

Best,

Jess

Re: Round Robin Calendar Issues - "Well This Is Disappointing"

ArisudanTiwari — Thu, 26 Jun 2025 12:31:25 GMT

Hi @LStier ,

This kind of error usually means there’s a hiccup with calendar sync or someone’s availability. Here are a few things you can try to troubleshoot:

Double-check calendar connections: Make sure everyone in the Round Robin still has their calendar properly connected in Settings > General > Calendar.
Test availability: Try removing all users and adding them back one at a time to see if a specific calendar is causing the issue.
Create a fresh Round Robin: Start with just two users to test, then add others gradually.
Try in incognito mode: Sometimes it's just a browser caching issue.
Share console logs with support: If it keeps happening, record what’s going on and send it (with console errors) to HubSpot Support.

Hope this helps.

Re: Round Robin Calendar Issues - "Well This Is Disappointing"

SanjayKumar — Thu, 26 Jun 2025 12:48:28 GMT

Hi @LStier,

I would like to share a few key suggestions that might help if you're running into issues with HubSpot's Round Robin scheduling

Check for Calendar Sync Errors: Even a single user with a calendar sync issue can break the entire round robin flow. It’s worth having each participant double-check that their calendar is connected and syncing correctly in HubSpot.

Confirm User Availability: Sometimes, the form lets you pick a time, but if none of the users are technically available (due to working hours, conflicts, or booking limits), the submission fails. Verifying availability through each user’s 1:1 scheduling link can quickly surface any hidden conflicts.

Rebuild the Round Robin from Scratch: Cloning an old scheduling link may carry over unseen issues or outdated settings. Starting fresh not just duplicating has helped some teams bypass form submission errors completely.

Isolate the Problem with Fewer Users: Try building a new round robin with just 2–3 users at a time (especially ones you've confirmed work individually). This makes it easier to pinpoint whether a particular calendar or user config is causing the breakdown.

Re: Round Robin Calendar Issues - "Well This Is Disappointing"

LStier — Thu, 26 Jun 2025 14:50:02 GMT

Hi there,

so we actually tried all of the above before posting here. None of those steps fixed the problem.

Oddly enough, our DBA found that the root of the issue stemmed from.a custom question we had that pushed to the Contact record. When that one specific question was removed, the system worked.

Re: Round Robin Calendar Issues - "Well This Is Disappointing"

Jaycee_Lewis — Thu, 26 Jun 2025 16:28:36 GMT

Hey, @LStier 👋 Thank you very much for taking the time to come back and let us know what worked. — Jaycee