Why isn't “String or Binary data would be truncated” a more descriptive error?

Question

To start: I understand what this error means - I\'m not attempting to resolve an instance of it.

This error is notoriously difficult to troubleshoot

Answer 1

Microsoft is lazy?

You don't have to try each row insert separately, by the way. Just query for max(len(field)) for each text column, starting with the ones you suspect might be the culprit.