Lessons from Migrating 28 Hosts to Debian 12 Using Ansible

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A team migrated 28 application and utility hosts from Debian 11 to Debian 12 over three evenings using ansible-core 2.17.7 in a pinned Python 3.12 environment. The cutover hit an unexpected snag at 02:13 when the last Debian 11 VM in the payments group stopped accepting the old OpenSSH cipher list mid-run. The exercise challenged common misconceptions about Ansible, including the belief that it is merely SSH with extra indentation, which the team argued obscures its real capabilities around idempotent modules, handlers, and inventory management. The varied host types — API nodes, Celery workers, reporting boxes, and Redis replicas — each had distinct configurations that benefited from Ansible's structured approach over ad-hoc shell scripts. Despite Ansible's strengths, the team noted it does not eliminate SSH pitfalls such as stale known_hosts entries or expired certificates, all of which were encountered in the weeks prior.

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