There is two extremes in the popular cloud space when it comes to ease of updating: Wordpress and Owncloud...
On one side is Wordpress which has about the most simple and most reliable update process that is fully automatic and doesn't even have to be triggered by the administrator for small upgrades and a simple click when going from one major release to the next. It hasn't failed me once in the past five years. And then there is Owncloud, which is the exact opposite.
Over the past year it failed me during each and every update with obscure error messages even for small security upgrades, broken installations and last resort actions such as deleting app directories and simply ignoring some warnings and to move ahead despite of them. If you think it can't be that bad, here's my account of one such update session last year. In the meantime I've become so frustrated and cautious as to clone my live Owncloud system and first try the update on a copy I can throw away. Only once I've found out how to run the upgrade process, which unfortunately changes every now and then as well, which things break and how to fix them do I run an upgrade on my production system. But perhaps there is some hope in sight?
My last upgrade a couple of days ago worked flawlessly, apart from the fact that the update process has changed again and it's now mandatory to finalize the upgrade process from a console. But at least it didn't fail. I was about to troll about the topic again but this morning I saw a blog post over at the Owncloud blog in which they finally admit in public that their upgrade process leaves a lot to be desired and that they have started to implement a lot of things to make it more robust and easier to understand. If you have trouble updating Owncloud as well I recommend to read the post, it might make you feel a bit better and give you some hope for the next update process.
And to the Owncloud developers I would recommend to go a bit beyond what they have envisaged so far: Blinking lights, more robustness and more information of what is going on during an update is a nice thing and will certainly improve the situation. In the end, however, I want an update process that is just like Wordpress'es: You wake up in the morning and have an email in your inbox from your Wordpress installation that tells you that it has just updated itself, that all is well and that you don't have to do anything anymore! That's how it should be!