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I keep reading conflicting information about upgrading from 14.04 to 15.10. This post here suggests that in order to upgrade to 15.10, I first need to upgrade to 14.10 and then 15.04 before 15.10, and skipping upgrades in between is generally a bad idea.

That's all well and good, but when I try to follow the instructions in the post, I get this when running do-release-upgrade -d:

Err Upgrade tool signature                                                     
  404  Not Found [IP: 91.189.92.200 80]                                        
Err Upgrade tool                                                               
  404  Not Found [IP: 91.189.92.200 80]                                        
Fetched 0 B in 0s (0 B/s)                                                      
WARNING:root:file 'utopic.tar.gz.gpg' missing
Failed to fetch
Fetching the upgrade failed. There may be a network problem. 

There is definitely no problem with the network.

If I run the GUI Software Updater (after having changed release-upgrades from lts to normal), it suggests skipping right to 15.10!

On top of this, I then read the answer here that I can actually skip directly between LTS versions. I don't mind waiting for 16.04 LTS if I need to, but I'd prefer to do the incremental upgrades if its going to result in a more reliable system.

Could someone please explain the truth to me here? Because these seem contradictory.

EDIT: I tested the same steps on another machine also running 14.04 LTS, and the do-release-upgrade -d command worked, however it tried to upgrade directly to 15.10 and completely broke the system (wouldn't boot). So it seems like going directly to 15.10 is still a terrible idea. So what is the alternative upgrade path? Do I need to reinstall from scratch?

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LTS to LTS is an officially supported upgrade path. https://help.ubuntu.com/community/UpgradeNotes Considering 16.04 comes out soon, your best bet is to wait for that.

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Upgrade from 14.04 or 15.10 to 16.04 https://help.ubuntu.com/community/XenialUpgrades

Short version

Do:

do-release-upgrade

instead of

do-release-upgrade -d

More resources with possible arising problems

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