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Cork oaks highly infested by Cerambyx welensii emit an amount of limonene at dusk, when C. welensii adults become active. In contrast, emissions by neighboring cork oaks free of C. welensii are dominated by pinene-type compounds. The activity of the woodborer Cerambyx welensii Kuster is a key factor in the decline of Quercus suber L. dehesas. This study aimed to estimate whether trees highly infested by C. welensii exhibited a peculiar emission profile, with known antennally active compounds. Monoterpenes were sampled in situ in 2006 (day/late evening) and 2008 (early evening) from Q. suber stratified by whether or not trees were highly infested by C. welensii and analyzed by gas chromatography. Limonene, α-pinene, β-pinene, sabinene, and myrcene accounted for over 87.2% of overall monoterpene emissions. Monoterpene composition and emission rates differed between the two groups, both during daytime and early evening, with a high presence of limonene in infested trees and dominance of pinene-type compounds in non-infested trees. This work evidenced differences in foliar monoterpene emissions between Q. suber trees highly infested by C. welensii and non-infested trees, with a high presence of limonene in the former and dominance of pinene-type compounds in non-infested trees. We hypothesize that the detection—especially during the onset of insects daily flight—of certain compounds (e.g., limonene), together with the detection of specific ratios of several monoterpenes (e.g., those of limonene to pinene-type compounds), has a role in the intraspecific host selection by C. welensii.