Southern pine beetles (Dendroctonus frontalis Zimmermann) and symbiotic fungi are associated with mass mortality in stands of Caribbean pine (Pinus caribaea Morelet). This study provides a 12.7-year assessment of semiochemical mediation between southern pine beetle and Caribbean pine in relation to concentrations of 4-allylanisole (estragole, methyl chavicol) and monoterpenes measured by gas chromatography–mass spectrometry in different seasons in premontane and coastal pine stands of Belize and Guatemala. Individual trees and stands with >2.5% (relative mass %) of 4-allylanisole in the xylem oleoresin exhibited significantly less beetle-induced mortality than those with <2.5%. Changes in relative levels of 4-allylanisole and monoterpenes during this study are consistent with seasonal temperature and cumulative water deficit effects and suggest bark beetle attack of P. caribaea may intensify in the future.