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WorkOS
The modern identity platform for B2B SaaS. The APIs are flexible and easy-to-use, supporting authentication, user identity, and complex enterprise features like SSO and SCIM provisioning.
First, install deprecation toolkit: https://github.com/Shopify/deprecation_toolkit. This will let you record every deprecation warning that fires while running your test suite and basically give you a “todo” list of most of what you need to fix to establish a safe upgrade path.
Second, setup a dual boot with the next rails version using either bootboot https://github.com/Shopify/bootboot or managing multiple gemfiles. Read up on dual booting rails and get the tests running and the amount of failures should give you a rough idea of how much work is involved in the upgrade.