A year after joining PagerDuty, the author faced challenges with the deploy time of their growing Rails application, which had expanded to a distributed and service-oriented architecture. Initially, code deployment to production took about 30 seconds, but it eventually stretched to 6-10 minutes, hampering development speed and enjoyment. To optimize deploy times, the team utilized Capistrano with custom configurations to measure performance bottlenecks. They successfully reduced deploy time to 50 seconds by pruning old git tags, selectively recompiling assets, and using Monit for efficient background job management. Asset-heavy deploys were sped up by avoiding unnecessary recompilations, and background worker restart times were reduced by switching from a synchronous process to a Monit-managed rolling restart. The deploy_test:web_trigger task was also optimized by running it asynchronously. Despite significant improvements, asset compilation remains a challenge, with proposed solutions including pre-minified vendor assets and using continuous integration servers for asynchronous asset building. The overall improvements have facilitated more frequent and efficient deployments.