Analyses of pentane extracts of frass, whole beetles, and volatiles trapped on Porapak-Q from Pityophthorus Eichhoff spp. fed on Pinus radiata D. Don demonstrated that (E)-pityol [2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran] was produced by male Pityophthorus carmeli Swaine, female Pityophthorus nitidulus (Mannerheim), and female Pityophthorus setosus Blackman. (E)-(−)-Conophthorin) [(5S,7S)-(−)-7-methyl-1,6-dioxaspiro[4.5]decane] was produced by male P. carmeli and male P. nitidulus. Only the (2R,5S)-(+) stereoisomer of (E)-pityol was produced by male P. carmeli and female P. setosus. In field bioassays in central coastal California, P. setosus was attracted to (E)-(+)-pityol, whereas P. carmeli responded only to a combination of (E)-(−)-conophthorin and (E)-(+)-pityol. Male P. setosus and female P. carmeli responded to these treatments with larger numbers than opposite-sex conspecifics. (E)-(−)-Conophthorin alone did not attract species of Pityophthorus but significantly reduced catches of P. setosus to (E)-(+)-pityol. Lasconotus pertenuis Casey (Coleoptera: Colydiidae) and Ips mexicanus (Hopkins) (Coleoptera: Scolytidae) were attracted to a combination of (E)-(−)-conophthorin and (E)-(+)-pityol, and showed a trend for attraction to all (E)-(−)-conophthorin-containing treatments. (E)-(−)-Pityol was neither attractive nor interruptive for any taxon. (E)-(+)-Pityol is shown to be an aggregation pheromone component for P. carmeli and P. setosus. (E)-(−)-Conophthorin functions as a pheromone component for P. carmeli and may also function as a synomone that decreases competition of P. carmeli and P. nitidulus with P. setosus and as a kairomone for L. pertenuis. These semiochemicals have been useful in studying relationships among twig insects and the pathogen Fusarium circinatum (Nirenberg and O’Donnell), causal agent of pitch canker disease in P. radiata.