Two pathways have been considered in the fluorination of CB5H6-and CB9H10- by HF. In the ionic HF fluorination pathway, the monocarborane anion cage is first protonated in a BBB face followed by H-2 elimination and fluoride anion addition. In the covalent HF fluorination pathway, HF is first coordinated through hydrogen to the BBB face. Next, the fluorine can add to either an axial or equatorial boron atom which opens the cage to a nido structure with an endo fluoride substituent. Endo to exo rearrangement occurs with a small activation barrier followed by H-2 elimination. In both pathways, fluorination at the equatorial boron position is predicted to have smaller activation barriers even though substitution at the axial position leads to the more stable products.