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I need some free software to help me easily produce an interactive - searchable/collapsible HTML manual for a software product. It is mostly with educational purposes.

Also, I am looking on some background on designing manuals in software development, a book on the subject, or a series of nice articles on the history of software manuals, file formats, tools, goals, templates etc. would be great too.

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Have you considered Sphinx? It takes RST files and converts them into HTML and PDF, we use it to generate all the documentation for GeoServer, it's easy to keep it in version control and automatically generate it with new builds.

The home page highlights these features:

Output formats: HTML (including Windows HTML Help), LaTeX (for printable PDF versions), ePub, Texinfo, manual pages, plain text

Extensive cross-references: semantic markup and automatic links for functions, classes, citations, glossary terms and similar pieces of information

Hierarchical structure: easy definition of a document tree, with automatic links to siblings, parents and children

Automatic indices: general index as well as a language-specific module indices

Code handling: automatic highlighting using the Pygments highlighter

Extensions: automatic testing of code snippets, inclusion of docstrings from Python modules (API docs), and more Contributed extensions: more than 50 extensions contributed by users in a second repository; most of them installable from PyPI

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