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I assume you have correctly identified your plum curculio problem based on the diagnostic crescent-shaped wounds the female makes during the 30-day egg-laying period:
The adults overwinter in the top few inches of leaf litter. They initially appear in apple orchards during bloom. Most activity occurs during the first warm period after petal fall, when the temperature reaches 70°F or higher. Adults can be found in orchards for 5 to 7 weeks. Egg laying activity starts once the fruit begins to form. There are two strains of plum curculio in Virginia. The northern strain has a dormant chilling requirement and only a single generation per season. The southern strain lacks this chilling requirement and can develop two generations seasonally. A rough dividing line for these two strains parallels the Blue Ridge Mountains to northern Virginia, then curves east through Delaware: http://www.virginiafruit.ento.vt.edu/pcmap.jpg
Control with Surround (kaolin clay) should start immediately at petal fall and continue through the end of the 30-day egg-laying control period. Sprays may need to be repeated every 7 days. If this schedule with Surround doesn’t give satisfactory results, you might try including a pyrethrum/ pyethrin product with apples on the label. In your case, the oil spray is ineffective and too early. Depending on what insecticide is in your “fruit tree spray”, it may also have been ineffective although your timing may have been correct. I suspect much of your damage is occurring soon after bloom, well before the fruit is 1 inch in diameter. A more intense Surround/ pyrethrin schedule can cause an increase in mites, so it is helpful to continue to use your oil spray to suppress early mite egg hatch.
Better luck this year!