Cloudron Forum

Hi everyone,
I'm running Cal.com on Cloudron and I'm trying to update to the latest package version (2.13.0 / Cal.com 6.2.0) but I'm running into issues. I'd appreciate any help.
Current setup:

Cloudron version: 9.0.17
Cal.com package version: 1.14.12 (Cal.com 4.7.14)
Server: Ubuntu 20.04 on Hetzner

The problem:
We are experiencing intermittent email delivery failures. Booking confirmations are only sent to attendees in roughly 90% of cases — the other 10% never arrive. The issue is not consistently reproducible. We are hoping that updating to the latest package might resolve this.
What we tried:
The Cloudron update button only offers us package 1.14.13 (Cal.com 4.7.16) as the next step — not 2.13.0 directly. We tested updating to 1.14.13 multiple times today, but every time the public booking pages returned a 404 error after the update (e.g. meet.example.com/username/30min). We had to restore from backup each time.
Questions:

Is it possible to skip directly from 1.14.12 to 2.13.0? If so, how?
Is there a known issue with package 1.14.13 breaking public booking pages (404 on /username/eventslug)?
Are there any additional manual steps required for the 2.x major update beyond the new API subdomain?

Thank you in advance!

Hi, thank you so much for the detailed breakdown – this is exactly what I needed! It's great to have a clear step-by-step path forward.
I'll follow your guide and work through the upgrades carefully. Good to know about the backup configuration file – I'll make sure to secure that before doing anything else.
For now I'll try to handle this myself, but I'll definitely keep the partner support option in mind in case I run into trouble. I'll report back once I've gone through the steps!

First of all, thank you so much for your detailed and helpful answers!
I recently gained access to our company's server and I'm trying to tidy things up. There have been over a hundred notifications on the Cloudron dashboard that had been ignored for a long time. I'm working on getting everything up to date, but since I don't have much practical experience and am fairly new to server administration, I'm being rather cautious and taking things step by step.
Based on your feedback, I now understand the correct order of operations. My plan going forward is:

Upgrade Cloudron to the latest version first
Then upgrade Ubuntu 20.04 to 22.04 (or 24.04)
Then sequentially update Cal.com through each package version

Could you advise whether it is safer to upgrade Cloudron first or Ubuntu first? And is there anything specific I should watch out for given that Cal.com booking pages are currently breaking on update to 1.14.13?
Thank you again for your patience with a newcomer!