Thank you for your suggestion! We try to pass along as much information about validation errors as possible, and will continue to review them. The validation errors are drawn directly from Salesforce, so we can be limited by how much information Salesforce provides to us over the metadata API. You can replicate validation or deployment errors in Workbench to confirm that the messages are coming from Salesforce. If you ever need more information about an error message, please feel free to reach out via the in-app chat window and we’ll do our best to provide more information when it is available! :)
The errors you see during gearset validation are actually coming from salesforce itself through Metadata API. So, I don't think gearset can help with that.
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