HappyDoc is a tool for extracting documentation from Python source code. It differs from other such applications by the fact that it uses the parse tree for a module to derive the information used in its output instead of importing the module directly. This allows the user to generate documentation for modules which need special context to be imported.
rest2web is a tool for automatically maintaining Web sites or parts of Web sites. It integrates with docutils so that contents can be kept in reStructured Text or HTML. It has a powerful templating and macro system and can automatically generate index pages and navigation trails (like sidebars and breadcrumbs). It generates static HTML and can generate relative links, which means that sites can be viewed from the filesystem. A "uservalues" system assists with creating sites in multiple languages.
Rextile allows you to build XHTML documents and entire Web sites with ease. You write text using Textile (a format much more concise than XHTML), automate document parts with Ruby scripting, and generate the site offline (the server gets static XHTML). Rextile was inspired by Xilize. It uses RedCloth to convert Textile to XHTML, erb to run script blocks, and Hpricot for DOM manipulation.
JCite makes it possible to cite snippets of Java source code in your HTML documents (API documentation, for instance). The snippets are copied out of Java class source files, which should be part of the regular build. This guarantees that the cited snippets are always up-to-date. If you cite from unit tests, you even get the guarantee that they still work correctly. Finally, thanks to the excellent Java2Html library, the cited snippets get automatic syntax highlighting.