Hi @CoachScott
Welcome to the Zapier Community!
Sounds like you’ve got a great mix of tools — and yes, Zapier can definitely help you stitch them together to prevent double bookings and keep things in sync across calendars and Pipedrive.
At a high level, what you’re aiming for would likely involve setting up Zaps that:
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Watch for new events in either Google (New Event trigger for example) or Microsoft Outlook (“New Calendar Event” trigger for example) calendars,
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Cross-check that time window against the other calendar, and
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Optionally block time, reschedule, or even update relevant records in Pipedrive.
Since you also use TidyCal, you could trigger Zaps using the “New Booking” trigger and then create/update events on both calendars, or log them into Pipedrive.
Please take a look at all triggers and actions available for TidyCal here:
https://zapier.com/apps/tidycal/integrations
I hope this helps!
Thank you very much on all levels, Sebastian!
I spent about 2 hours this afternoon trying to make this work and I failed...miserably. 
Hey there, @CoachScott 
I just came across this and wanted to check on your progress. Were you since able to get it working?
If you’re still stuck at all, feel free to send over some screenshots of the Zap set up, as well as any error messages you might be seeing and we’ll be happy to lend a hand. Just be sure to use a tool like Zappy to remove any personal info like names, emails etc. before posting here.
Looking forward to hearing from you!
Hey @CoachScott,
Saw that you need help with syncing calendars to avoid overbooking with CRM sync. Can understand how frustrating it can be to set it up as it can get technical and not able to achieve the desired workflows. Can you let me know me the exact workflows that you are trying to automate and more about your business?
PS: If you need any professional help and a done for you service, I am a Zapier Official Silver Solution Partner and you can contact me through my solution page here or just send a DM from my profile :)
Many thanks for the reply and I do need professional help! 
As for workflow, the mistake I made with PipeDrive was that I did not know they could not filter “child” (domain alias) when it comes to email for Google Workspace. As a result, I signed up for the most basic Microsoft 365 account and am using that for PipeDrive. That has caused other issues that are leading me to look at other CRM’s like Streak or Go High Level. That said, I have already paid for PipeDrive for one year so if I could fix this, that would be great,
Here is the workflow that I need, bottom line.
Whether someone schedules time with my via TidyCal, Google Workspace, PipeDrive or Microsoft 365, Zapier will make certain that there are no conflicts (i.e., Doctor appointment on my personal (Google) calendar but someone wants to schedule a consult with me (Microsoft calendar) for business, it will not permit that and make certain I am not double-booked.
Does this make sense? Can you help me?
Hey @CoachScott,
Will you send a DM to talk more in detail. I can understand how frustrating it can be for you, will see what we can do as I have experience with Pipedrive as well.
Yes, I can help with the workflow that you described. Let talk more in DM :)
Hey @CoachScott and @Sparsh from Automation Jinn 
Once you’ve built this out, we’d love for one of you to share details of it here so others in the Community can give that approach a try too. Thanks! 
Hey @CoachScott and @Sparsh from Automation Jinn 
Once you’ve built this out, we’d love for one of you to share details of it here so others in the Community can give that approach a try too. Thanks! 
I will @SamB! I am thinking the simplest and most affordable solution is “zapping” PipeDrive with TidyCal but that is TBD.