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The NaNoWriMo website is the main hub for all NaNoWriMo activity.
According to Chris Baty, the initial website was created for year two, in 2000.
The Nanowrimo website sees the most traffic in the few days leading up to and following November 1. Historically, the website was continually underpowered for the sort of traffic it would only see for a week; Chris Baty related the problem in corndog-related terms. The downtime grew smaller as the years progressed and the technology on the website improved; the advent of Ruby on Rails saw the first year that the website did not go down to server traffic. (It does still occasionally go down to technical errors, despite the best efforts of Nano HQ and the thorough testing of the Beta Buggers.))
NaNoWriMo website features
The largest part of the website by far, and the part that sees the most traffic, is the NaNoWriMo forums.
What the NaNo site runs on
What the NaNo site runs on has changed over the years.
Yahoo! Groups (2000-2001)
Yahoo! Groups is a collection of user-run e-mail lists with additional features (such as being able to read content from the website instead, uploading files, and so on.) Prior to the creation of the forums, Nanowrimo participants collected via a Yahoo! Group to exchange tips and support. This worked well in Nano's second year, when the participation was around 140. It did not work so well the third year, when the participation exceeded 5,000. The official means of gathering were switched over to a forum system for 2002.
PhpBB is a bulletin board system that was popular in the early 2000's. The Nanowrimo website used PhpBB for its forum system from the forum's creation in 2002 until 2004.
Since PhpBB is only a forum system, it does not feature any content management or any methods for load balancing or managing database queries. It also has poor defenses against spambots (an increasing problem over the internet) so it is not as popular nowadays. These options became necessary to handle Nanowrimo's increasing traffic, so it was eventually abandoned in favor of Xoops after the 2004 season.
Xoops is a content management system and the one the NaNoWriMo site ran on from 2005-2006. Due to being a content management system as opposed to simply a forum, XOOPS could handle static content (such as webpages) as well as a forum, which is what the tech team was looking for at the time. The NaNo site, including the new Script Frenzy site, moved from Xoops to Drupal in time for the 2007 season.
Nanoedmo currently runs on Xoops.
Drupal is what the NaNo and Script Frenzy websites ran on, 2007- 2010. Script Frenzy used it right up until its shutdown in 2014 following its discontinuance in 2012. The Young Writer's Program, a site with smaller server loads than the main site, also uses Drupal, but is slated to move to the current framework, Ruby on Rails, in 2015. Drupal allowed for better site management than Xoops and supported better server support, but ultimately became unmanageable with Nano's growing traffic.
According to the Drupal website, it is "open source software maintained and developed by a community of 630,000+ users and developers." 
Ruby on Rails (2011-present)
Ruby on Rails (often shortened to RoR or Rails) is a web application framework for the Ruby programming language and the current framework of the NaNoWriMo website. Like xoops and Drupal (but unlike PhpBB), it is a website management system, which means that it can maintain both static or mostly static content (such as webpages), blog-type content, and forums. Since it is not primarily a forum system, and due to Nano's unique needs (such as a word count function), many of its modules are custom written by Dan Duvall.
The transition to Ruby on Rails from Drupal was chosen for RoR's better management of database queries and server management, which lowered the loads on the database by 75% and has so far put a permanent end to the October/November crashes that NaNo often endured in the 2002-2010 era. The transition began in 2011 with the Camp NaNoWriMo website, and then the NaNoWriMo Website later that year. Due to budget cuts, Script Frenzy remained on Drupal until its closure.
Fun fact: Many Nano users may interact with Ruby on Rails off the Nano site, as it is also used for the user interface on Twitter as well as websites like Github and Groupon.
Other Nano-function websites
StayClassy is the website Nano uses for crowdsourced individual fundraising, and is also the official system for raising funds to attend the Night of Writing Dangerously. Users can create and customize a page for enticing visitors to make donations. Its functions include custom text and pictures, the ability to add video, and custom shortened links. The website accepts Paypal and major credit cards.
Nanowrimo has started using Uservoice as a support system. It now houses the official FAQ as well as allowing for users to report bugs and request features. It is not, however, required for bug reporting or feature requests as the Site and Message Board Feedback and Suggestions and Tech Help & Site Bug Reports will continue to be fully supported.
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