Recent research found that cloud data warehouses are text-heavy. However, their capabilities for efficiently processing string columns remain limited, relying primarily on techniques like dictionary encoding and prefix-based partition pruning. In recent work, we introduced string fingerprints - a lightweight secondary index structure designed to approximate LIKE predicates, albeit with false positives. This approach is particularly compelling for columnar query engines, where fingerprints can help reduce both compute and I/O overhead. We show that string fingerprints can be optimized for specific workloads using mixed-integer optimization, and that they can generalize to unseen table predicates. On an IMDb column evaluated in DuckDB v1.3, this yields table-scan speedups of up to 1.36$\times$.