Worked on the timescale/tiger-cli repository to enhance the onboarding process and improve resilience in configuration directory setup. Focused on backend development using Go, the work addressed scenarios where the configuration directory is not writable by implementing robust error handling and providing clear user guidance. The solution included suggesting the use of the TIGER_CONFIG_DIR environment variable, which helps users resolve setup issues more efficiently. Additionally, a regression test was added to ensure that the error message reliably includes this guidance. These changes reduced user confusion, lowered support friction, and strengthened configuration reliability for both first-run and continuous integration environments.