I decided to install 13.10 on a WD my passport external HDD, and I thought I had everything all worked out with the partitions, but after loading up the desktop I hit the auto-software update and it said that '\boot' had insufficient space, it needed another 57(?) MB to complete the operation. I had given \boot 100MB and was led to believe that would be plenty.

My other issue is that ubuntu is being bypassed completely by windows 8 (not 8.1) on startup. I was hoping for some type of option to be given, but instead I have to interrupt startup and manually boot from USB.

The boot device was set to the external.

I will probably reformat the drive and try again. Any tips would be appreciated.

You don't need a separate /boot, but if you do choose to create one for some reason, I think 100mb is much too small. Official Ubuntu documentation recommends 1gb: https://help.ubuntu.com/community/BootPartition

You would have to tell windows to also boot from other devices. Dunno how to do it. But sure there are some tutorials on the web.

Ubuntu tends to save every kenerl it once knew about. So maybe see if you can delete some old ones which I doubt due to the fresh install. So yeah 250mb at least for boot should be fine. Take a look at how big the directory is now and multiply by five.

Alright, so probably skip the /boot, and the startup is dictated by the windows side? I'll look into that. Thanks

A kernel update wipes out /boot space usually??? It isn't easy to expand it on most installs.

Depending on a number of things, boot may be quite needed. It tends to be a distance on the drive where the boot files reside that cause one to use /boot. Just make /boot larger.

I'll reinstall with a bigger /boot, then.

As far as my start up, it seems like easyBCD is the tool I should be looking at. Or do I have to actually install a linux partition on my windows drive?

You don't have to reinstall to make partitions bigger/smaller... your Ubuntu Live DVD/USB should have the GParted partition editor.

Something else that you might want to know- do NOT make a swap partition on a flash drive. A swap area is basically used like extra RAM if it needs it. While this can be good on a regular HDD, the little memory cells of a flash drive have a limited life (about 10,000 writes, if I remember correctly). Using it as RAM will wear it out a lot faster.

If I'm wrong on this, someone please correct me, but from everything I know, swap on flash drive == bad idea

[EDIT]: I just re-read this and realized that you're using an HDD, which should perfectly fine for swap.

And you don't really need a separate partition for /boot, unless you're an advanced user who has a dozen distros on the drive. (An considering this is the "newbie" forum, I think this is unlikely ) I would suggest formatting about 6 GB (depending what your distro needs) of EXT4 (wht Linux actually installs on). Then I format the rest as FAT32 and choose it to mount as /windows. That way, I have a common ground between Windows and Linux.
But then again, this is your drive, so do whatever you want to do with it.

@Jefro I have an install of Ubuntu Studio which once had 8 kernel with initrd laying around. So either I don't understand you ??? right but for my installation the kernel live happy ever after. And if a kernel update would wipe the whole /boot what about self compiled kernels?

@maples 6GB are to low. Again my Ubuntu Studio also quite loaded right now goes with 8GB of installed software. Only software with home on a different partition. So definitely go with 20G if only use one partition. Also your hint for FAT32 is just downward bs.