Hyperconjugative and electrostatic interactions effects on (1)J(CH) spin-spin coupling constants (SSCCs) are critically studied from both theoretical and experimental points of view. A qualitative model is used to predict how the former affect such SSCCs, while electrostatic interactions are modeled with a point charge placed in the vicinity of the corresponding sigma(CH) bond. Hyperconjugative interactions are calculated using the "natural bond orbital" approach, and using the point-charge model, it is shown how intertwined are both types of interactions. Several members of the series 1 -X- bicyclo [ 1. 1. 1] pentane and 1-X-3-methylbicyclo[ 1. 1. 1] pentane are chosen as model compounds for measuring (1)J(CH) SSCCS; in some of them were performed also DFT-SSCC calculations. The strained cage substrate in these series defines strong sigma-hyperconjugative interactions, making these compounds excellent examples to verify the qualitative model presented in this work. It is verified that (a) hyperconjugative interactions from the sigma(CH) bond or into the sigma*(CH) antibond containing the coupling nuclei yield a decrease of the corresponding (1)J(CH) SSCC and (b) hyperconjugative interactions from other bonds involving the coupling C nucleus yield an increase of that (1)J(CH) SSCC.