Highly explosive Plinian eruptions of basaltic magma are enigmatic because low melt viscosities should inhibit such eruptive style. Masaya volcano, Nicaragua, is a persistently active basaltic system capable of a wide range of eruptive styles, from open-conduit lava lake activity to voluminous Plinian eruptions; it is thus an ideal natural laboratory to constrain potential controls on basaltic eruption style. Here we report the major, trace, and volatile (CO2, H2O, S, Cl, F) element composition of olivine-, plagioclase- and clinopyroxene-hosted melt inclusions as well as matrix glasses from lava lake ejecta and two Plinian tephra deposits—the 2.1 ka Masaya Triple Layer and the 1.8 ka Ticuantepe Lapilli—to test whether pre-eruptive volatile contents and degassing history may be linked to eruptive style. All samples display a relatively narrow and largely overlapping basaltic–basaltic andesitic compositional range (51.7±1.0 wt.% SiO2, 4.8±0.4 wt.% MgO) with similar trace element signatures (e.g., Ce/Y=0.82±0.10, Ba/La=74±11). However, lava lake and Plinian samples show systematic differences in pre-eruptive volatile contents, forming distinct groups with mean H2O contents of 0.6±0.2 wt.% (lava lake), 1.1±0.2 wt.% (Masaya Triple Layer), and 1.9±0.3 wt.% (Ticuantepe Lapilli). Together, these groups generate broad positive correlations between S, Cl and H2O concentrations, with maximum values reaching 920 ppm, 1300 ppm and 2.3 wt.%, respectively, which are low compared to typical Central American arc magmas. Magma temperature estimates overlap and average at 1115±30°C, while volatile saturation pressures are low, mainly <100 MPa, although only lava lake samples record pressures <31 MPa. These observations reiterate the compositionally buffered state of the volcano's magmatic system highlighted by previous work and demonstrate that — regardless of eruption style — all Masaya magmas undergo variable, but extensive, pre-eruptive degassing at low pressure. Geohygrometry, gas emissions, and H2O/Ce–Ba/La systematics suggest initial, undegassed H2O contents on the order of 3.9–5.5 wt.%. Our results imply that pre-eruptive volatile contents are not the culprit for Plinian events at Masaya. Instead, we propose that the volcano's vigorous magma supply is modulated in a top–down manner to produce a wide range of eruptive styles, whereby temporary sealing of the conduit may instigate a transition to explosive behavior. In this model, rapid magma ascent is triggered when the seal eventually breaks from degassing-induced pressurization, yielding high degrees of undercooling, rapid microlite growth, and a dramatic increase in magma viscosity and explosive eruption potential. There may thus be a thin line between open-conduit conditions and Plinian eruptions at Masaya.