TLDR:
Infield automates away the toilsome parts of keeping Rails apps up to date. If you've ever run bundle outdated or railsapp:upgrade then you want to use Infield. You can try it out for free at (https://app.infield.ai/trial)

Background
I started as a consultant that did Rails upgrades only. As I did these projects I found myself running into the same problems over and over and feeling like software could help. Very little of the time spent upgrading packages is spent writing code. It’s spent prioritizing new releases, breaking complex upgrades down into small steps, researching changelogs, and assessing risk. That's why we're building Infield - we use AI to help automate upgrade research and use that research to automate project management.

How it works
We scan your dependencies and produce a dashboard that answers the question "Which packages should I upgrade, in what order?". We prioritize package upgrades that are high impact (e.g., security fixes, getting away from abandoned packages) relative to effort (are there breaking changes? is upgrading this package blocked on upgrading something else?). We have this data because we use GPT to read the changelog for every package you depend on.

When you have a larger upgrade that can't be tackled in a normal maintenance rotation you use our Upgrade Path feature to break it down. Our software takes a major upgrade (like Rails) and turns it into a series of small, individually backwards compatible steps that accumulate in the upgrade.

Please check it out and write to us with any feedback at founders@infield.ai.