The Keanakāko‘i Tephra was deposited from 1500 to ca. 1820 CE, when Kīlauea’s magmatic output was ~2% of the average output during historical times (post–1823 CE). The tephra consists of deposits from numerous phreatomagmatic and phreatic eruptions, three episodes of high lava fountains, and one lava. Fresh glass is available from most tephra units. Major elements and trace elements were determined for glass from 49 tephra units and three pretephra lavas. Olivine crystals from 11 high-MgO tephra glasses were also analyzed. These results were compared to compositions from Kīlauea’s historical period to evaluate ~500 yr of Kīlauea geochemical evolution. Keanakāko‘i Tephra glass composition ranged widely (e.g., 3.4–11.2 wt% MgO). The observed large variations in FeO, CaO, TiO₂, and K₂O at a given MgO indicate numerous compositionally distinct parental magmas, with the two early nineteenth-century pumice eruptions showing the most diverse compositions. These two magmas were erupted on opposite sides of the caldera and probably tapped different magma bodies. The common occurrence of high-MgO olivine compositions (forsterite [Fo] 88%–89%) in MgO-rich tephra glasses indicates that primitive magma (Mg# 73–74) was routinely supplied to Kīlauea’s summit. Wide ranges and reverse zoning in olivine core compositions from some units show that magma mixing occurred before some eruptions. Modeling of compositional variations within Keanakāko‘i Tephra units using alphaMELTS showed that the most consistent trends for crystal fractionation involved shallow magma (1–2 km), with low water content (0.2 wt% in parental magma) and oxygen fugacity just below the quartz-fayalite-magnetite (QFM) buffer (–0.5 log units). Keanakāko‘i Tephra glasses have lower La/Yb and Nb/Y ratios than historical Kīlauea lavas. Low ratios have been observed during periods of high magma output for historical lava, which is inconsistent with the low magma output at Kīlauea’s summit during 1500–1820 CE. The most likely explanation for this inconsistency is endogenous growth within Kīlauea during this period, following formation of the modern summit caldera. No correlation was found between glass chemistry and eruption style for Keanakāko‘i Tephra deposits. Glass samples from many explosive units have lower Nb/Y and La/Yb ratios compared to glass from high lava-fountain units and historical effusive eruptions. The explosive character of Keanakāko‘i Tephra eruptions was probably caused by interaction of magma with shallow or surface water.