Linux Update Went Wrong, Why?

I recently had to reboot a Linux system I'm working on and since this system doesn't get rebooted often, I decided to do an update to bring the system current.

After running sudo apt upgrade (which started fine,) the service started complaining that it was out of space.

It finally exited with code 1 and gave that message again about being out of space. I assumed the updates didn't install and that Linux had been smart enough to roll back (one would assume with such a mature system, it would have.)

So I rebooted it in the hopes of trying the update again.

It never got to the boot screen. There was someone working in the data center at the time and I had to get them to look at the screen (I only access it over SSH.) They said it looked like it was showing a bunch of processes and just sitting there (I'm assuming it looked like a ps dump.)

So I had them hard boot the system and go into the Advanced menu. From there I first had them activate "clean broken packages" and then boot into an older kernel. That older kernel works, and the Linux system is able to boot fine now.

I have several questions here:
1. Why wouldn't Linux just refuse to update if there's not enough space?
2. When logging into SSH, it says 10% of / used... so the system definitely isn't low on hard disk space. Where did it run out of memory and how do I prevent this in the future?
3. Is there any way to recover the latest Kernel? or
4. Is there a way to get rid of the latest kernel and just force Linux to boot the good kernel (the one that's running now?)

I did run apt autoremove which cleaned up a lot of stuff. It's asking me to reboot (***system restart required***) when I log in to SSH but I'm afraid to do that without someone present in the data center. It did mention stuff about removing kernels while performing autoremove.

Also sudo apt update now says 0 packages can be updated. So I guess it actually did update? I'm so confused at this point. Please help before I join the "Linux is complicated and cryptic" crowd. xD

I hope it didn't get rid of all the kernels on the system (what if the one I'm currently running gets corrupted? The only thing that saved me last time was that Linux happens to keep older kernels around.) I didn't even know it did this until I had someone in IT bring up the boot menu.

This is an Ubuntu system.

Also, if you can please keep your answers simple. It's IT's job to troubleshoot these systems and all that and I've never done anything on Linux machines except for software stuff you can do over SSH. So if you use Linux-specific terminology please explain what it means so I can understand. Remember, I'm not IT. I'm just a software guy. So my familiarity with this sort of thing is lacking (I'm even afraid to touch "Windows recovery options" when Microsoft gives us a nice friendly GUI to play with.)

Thanks!

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