The core of our in-house 19 F NMR chemical shift prediction throughout the years have been rooted fluorine fingerprints. They were described in as a variant of the path-based topological torsion count fingerprint using atomic numbers, number of π electrons, and number of heavy atom neighbors to generate bits. All paths up to a certain path length contribute to the set and the counts of bits in the fingerprints. This means a fingerprint with a path length of 7 will count all bits of the paths of length 7, 6, 5, and so on. Because fluorine fingerprints are count fingerprints, they will be compared using Dice similarity, which compares counts as well as whether a bit is present, instead of the more common Tanimoto similarity used for other fingerprints, such as extended connectivity fingerprints. Deviating from the original description, the fluorine fingerprints used in this publication always start their path at a fluorine atom. In the original publication, paths started at a fluorine atom for the CF motif and from the carbon of a trifluoromethyl group for the CF3 motif. The path length of the fingerprint was optimized as a hyperparameter (See Table of the supporting information).