Skip older Cal packages

[tom.westphal]

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!

[james]

Hello @tom.westphal and welcome to the Cloudron Forum

@tom.westphal said:

Cloudron version: 9.0.17

You are several Cloudron versions behind. Be advised that this will cause issues.

@tom.westphal said:

Ubuntu 20.04 on Hetzner

Ubuntu 20 has been EOL since May 2025, so almost a full year.
This is critical since you will only get security updates when you pay for Ubuntu pro.
This means your Ubuntu has received no security updates for almost a year.
Please upgrade your Ubuntu as soon as possible.
See:

• https://docs.cloudron.io/guides/upgrade-ubuntu-22
• https://docs.cloudron.io/guides/upgrade-ubuntu-24

@tom.westphal said:

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.

Cloudron does not offer version hopping.
You must upgrade sequentially to ensure that all database migrations are working to get to the latest version.

@tom.westphal said:

Is it possible to skip directly from 1.14.12 to 2.13.0? If so, how?

No and why is described above.

@tom.westphal said:

Is there a known issue with package 1.14.13 breaking public booking pages (404 on /username/eventslug)?

Since you are multiple versions behind on Cloudron, Ubuntu and @cal.com it is most likely exactly that.
You did not get the many features and bug fixed for Cloudron and @cal.com because you are this far behind with updates.

May I ask what led to this set up being this out of date? This could help us improve Cloudron to ensure systems stay updated or at least Cloudron might do a better job to inform the user of this issue.

[tom.westphal]

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!

[james]

Hello @tom.westphal

I understand your predicament.
Taking over a black-box which you had no access to before is always a struggle.

Ensure Cloudron Backups are working and you have the encryption password

Cloudron Documentation: backups

The first thing you should do is ensure that the Cloudron backup is working correctly.
If the Cloudron backup configuration has an encryption password configured, make sure you have that encryption password.
Otherwise, restoring from a Cloudron backup is not possible, since without the encryption password Cloudron will not be able to decrypt the backup.
If no encryption password is set you can ignore this.

Create a full Cloudron backup from the dashboard and download the backup configuration of the just created backup.
Save this file to your computer and make sure it is saved in a place where you remember it.
In case anything breaks, you can restore the full Cloudron server with this downloaded configuration file.

Upgrade Ubuntu 20 to 22

Follow the guide https://docs.cloudron.io/guides/upgrade-ubuntu-22

If everything worked out upgrade to 24

Upgrade Ubuntu 22 to 24

Follow the guide https://docs.cloudron.io/guides/upgrade-ubuntu-24

If everything worked out, perfect.

Update Cloudron

Update Cloudron from the dashboard.
Each Cloudron update can take some time depending on the version.
Some Cloudron versions have to re-create all docker containers which can lead to a downtime.
The downtime I can not estimate for your set-up since I have no knowledge about all the apps installed, at least there is one @cal.com

After each successful Cloudron update you can do some minimal testing if your apps still work correctly.

Update the @cal.com app

When Cloudron is updated to the latest version you can start updating your @cal.com app.
Each app update should create an app backup which you can jump back to if something goes wrong.
Please ensure that Automatic backups is not disabled for your @cal.com app.

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If you might need some help from a Cloudron partner, I could get you in contact with one of our partners that offer paid support for cases such as yours.

[tom.westphal]

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!

[sparkwise]

We've seen inconsistent email delivery even on the latest release, which I believe was due to issues specific to Google Calendar (our primary calendar service.) I filed an Issue and I saw a few PRs referencing this with a fix, but nothing was merged. Even if it had been merged, there hasn't been a new release issued on this repo in almost three months (down from multiple per week prior to the strategy change.) Hope to see it revived, but not counting on it.