I've previously written about Canonical's obnoxious IP policy and how Mark Shuttleworth admits it's deliberately vague. After spending some time discussing specific examples with Canonical, I've been explicitly told that while Canonical will gladly give me a cost-free trademark license permitting me to redistribute unmodified Ubuntu binaries, they will not tell me what Any redistribution of modified versions of Ubuntu must be approved, certified or provided by Canonical if you are going to associate it with the Trademarks. Otherwise you must remove and replace the Trademarks and will need to recompile the source code to create your own binaries actually means.
Why does this matter? The free software definition requires that you be able to redistribute software to other people in either unmodified or modified form without needing to ask for permission first. This makes it clear that Ubuntu itself isn't free software - distributing the individual binary packages without permission is forbidden, even if they wouldn't contain any infringing trademarks[1]. This is obnoxious, but not inherently toxic. The source packages for Ubuntu could still be free software, making it fairly straightforward to build a free software equivalent.
Unfortunately, while true in theory, this isn't true in practice. The issue here is the apparently simple phrase you must remove and replace the Trademarks and will need to recompile the source code. "Trademarks" is defined later as being the words "Ubuntu", "Kubuntu", "Juju", "Landscape", "Edubuntu" and "Xubuntu" in either textual or logo form. The naive interpretation of this is that you have to remove trademarks where they'd be infringing - for instance, shipping the Ubuntu bootsplash as part of a modified product would almost certainly be clear trademark infringement, so you shouldn't do that. But that's not what the policy actually says. It insists that all trademarks be removed, whether they would embody an infringement or not. If a README says "To build this software under Ubuntu, install the following packages", a literal reading of Canonical's policy would require you to remove or replace the word "Ubuntu" even though failing to do so wouldn't be a trademark infringement. If an @ubuntu.com email address is present in a changelog, you'd have to change it. You wouldn't be able to ship the juju-core package without renaming it and the application within. If this is what the policy means, it's so impractical to be able to rebuild Ubuntu that it's not free software in any meaningful way.
This seems like a pretty ludicrous interpretation, but it's one that Canonical refuse to explicitly rule out. Compare this to Red Hat's requirements around Fedora - if you replace the fedora-logos, fedora-release and fedora-release-notes packages with your own content, you're good. A policy like this satisfies the concerns that Dustin raised over people misrepresenting their products, but still makes it easy for users to distribute modified code to other users. There's nothing whatsoever stopping Canonical from adopting a similarly unambiguous policy.
Mark has repeatedly asserted that attempts to raise this issue are mere FUD, but he won't answer you if you ask him direct questions about this policy and will insist that it's necessary to protect Ubuntu's brand. The reality is that if Debian had had an identical policy in 2004, Ubuntu wouldn't exist. The effort required to strip all Debian trademarks from the source packages would have been immense[2], and this would have had to be repeated for every release. While this policy is in place, nobody's going to be able to take Ubuntu and build something better. It's grotesquely hypocritical, especially when the Ubuntu website still talks about their belief that people should be able to distribute modifications without licensing fees.
All that's required for Canonical to deal with this problem is to follow Fedora's lead and isolate their trademarks in a small set of packages, then tell users that those packages must be replaced if distributing a modified version of Ubuntu. If they're serious about this being a branding issue, they'll do it. And if I'm right that the policy is deliberately obfuscated so Canonical can encourage people to buy licenses, they won't. It's easy for them to prove me wrong, and I'll be delighted if they do. Let's see what happens.
[1] The policy is quite clear on this. If you want to distribute something other than an unmodified Ubuntu image, you have two choices:
Gain approval or certification from Canonical
Remove all trademarks and recompile the source code
Note that option 2 requires you to rebuild even if there are no trademarks to remove.
[2] Especially when every source package contains a directory called "debian"… comments