What happens when you build a site in Drupal 4.7 and just... keep updating it? For the next 18 years? The original www.smartsheet.com marketing site was launched in 2006, on the brand-new Drupal 4.7 platform, and it's been maintained ever since, following Drupal through versions 5, 6, 7, 8, 9, and 10, and expanding as Smartsheet grew from a tiny six-person startup to a publicly-traded $6B company. Some upgrades have proven harder than others: the Drupal 7 site upgrade didn't launch until three years after the Drupal 7 release, for example. Many of the site's early details have been lost to history, but the current team has a decade of institutional memory, which is plenty of time to make mistakes worth learning from. We'll talk about why we've never switched platforms, what tradeoffs we make for deployments with zero customer-facing downtime, and how to write custom code so that your future self won't swear at you too loudly.