A likely reason why consumers are not repeat buyers of many fresh-cut fruit is inconsistent or unsatisfactory flavor and/or textural quality. Research toward understanding mechanisms responsible for generation, and/or loss of flavor compounds in fresh-cut fruit is limited. Solid phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) were utilized to study flavor volatile profiles in anthesis-tagged cantaloupe (Cucumis melo L. var. reticulatus Naud. cv. Sol Real) during growth, development, and for fresh-cuts prepared from fruit with five distinctly different harvest maturities. One-quarter-slip fruit had a clearly green, well-attached peduncle; 1/2-slip fruit had a distinct abscission detectable at the peduncle, 3/4-slip fruit were approaching commercial harvest, full-slip (FS) fruit are or will cleanly separate from the vine with light pressure; and over-ripeness (OR) was precisely categorized as 2 days past FS. Recovery of total volatiles displayed a linear response and most volatile classes (except aldehydes) generally followed a trend upon processing where FS > 3/4-slip > 1/2-slip > 1/4-slip. On day 0, only 70.0%, 37.7%, and 20.5% total volatiles were recovered in 3/4-slip, 1/2-slip, and 1/4-slip fruit, compared to FS fruit. During fresh-cut storage, percent total esters followed an increasing linear trend that was maturity-dependent. Percent total aromatics and percent aldehydes followed a linear trend that was maturity-dependent whereby 1/4-slip > 1/2-slip > 3/4-slip > FS. During storage, the relative percentage of acetates decreased, and displayed a maturity-dependent curvilinear trend. The magnitude of the slope decreased with maturity, indicating that the effect of storage time decreased as maturity increased. In FS, 3/4-slip, 1/2-slip, and 1/4-slip cubes, acetates comprised 66.9% of all compounds recovered on day 0 yet, only 26.1% to 44.2%, and 21.3% to 32.6% remained on days 9 and 14, respectively. For all maturities, a curvilinear increase in relative percentage of nonacetate esters was observed during storage. There was a uniform change in the ester balance (nonacetate ester:acetate ratio) during fresh-cut storage, which was independent of initial processing maturity. The overall ester ratio changed roughly 2-fold after just 2 days in optimum storage, and after 5 days it increased more than 3-fold. The shift in endogenous ester compounds could be partially responsible for the apparent loss of characteristic flavor in fresh-cut cantaloupe through long-term storage.