We have extensive issues with the link breaking. Problems we see:

1) Activities in Redtail not blocking off the Calendly options. This most frequently happens with recurring activities - if you make an edit to them, often they stop flowing through causing double-booked appointments
2) Appointments from Calendly not being added into Redtail. Cannot identify a trend, but I have examples.
3) RT Calendar randomly stops syncing in Outlook without any notice.

Every time these issues come up, I am told to kill the RT to Outlook integration, re-enable and then update calendly. The problem is, when they come up, we have already double-booked or missed meetings. We need this to be iron-clad!

Our firm uses Redtail's Zimbra server for email and calendar services, and use Outlook desktop app. We don't use Redtail's CRM internal calendar.
Specific to this platform recommendation, we would like Redtail to urge Zimbra's developers work with Calendly so there would be a direct server sync. Currently we have to use Calendly's plug-in app with the PC and Outlook running to sync up, and it is a major system hog each time (I have it set for 1x/hr). Calendly already of course has a direct server-to-server integration with Microsoft 365/Exchange. But not yet with Zimbra's server.

Our firm currently uses a web of connections between Calendly, Redtail, Outlook and Zapier to make our Calendly items show up on Redtail properly. While it's no extra cost it's extremely annoying. If one password gets changed on any platform, you have to relink everything. I do this constantly for 4 advisors. Or clients love being able to schedule themselves. There MUST be something that can be done to make this integration easier.

It also needs to allow an automated workflow to begin.

This integration needs to insert the appointment setters name in "linked contact" field

All of these comments are accurate. Also, the workaround via Outlook calendar is not stable and has connectivity issues. Zapier has a solution but is expensive and not real time from what I see.

If you use Outlook, then you can integration by using the Calendly Outlook plugin. https://help.calendly.com/hc/en-us/articles/223144847-Getting-started-with-the-Outlook-Desktop-Plug-in#1

This would be tremendously useful for our team. Any update on this?

1. Every appointment created through Calendly shows up in Redtail as a Task - not as the specific appointment type that we would want.
2. The Event Name on the Redtail calendar shows the names of the attendees - NOT the actual event name or subject of the meeting created in Calendly.
3. Existing contacts already in Redtail do not appear to attach correctly to appointments created in Calendly. We want to link each client that schedules to the activity to log it correctly.

Right now I'm set up on Redtail Retreiver that's feeding into Outlook
Outlook and Calendly are synced.
When something is created in Calendly, I'm using Zapier to create a task in redtail.
The problem with zapier is that it won't let me distinguish between a phone call, meeting, out of office, etc.

Direct integration with Calendly (or similar) is needed! Right now, Redtail makes this "possible" via Outlook (Connect Calendly to Outlook and Redtail to Outlook) BUT the massive issue is that any appointment created via Calendly will not generate a workflow. For example, we have meeting types that each generate its own workflow, so we need the online scheduler to kickoff the workflow. Right now, we need to manually create a workflow whenever a client schedules, which is terrible...

We definitely need this!! We are testing the workaround that syncs through the Cloud Retriever for Office 365, but it is clunky and there are several issues:

1. Every appointment created through Calendly shows up in Redtail as a Task - not as the specific appointment type that we would want.
2. The Event Name on the Redtail calendar shows the names of the attendees - NOT the actual event name or subject of the meeting created in Calendly.
3. Existing contacts already in Redtail do not appear to attach correctly to appointments created in Calendly.

I understand that any type of workaround like this will always have issues. The only really good solution would be for Redtail to integrate directly with Calendly - like Calendly does with Salesforce.

Hopefully you can put that on the docket for the near future??