Before the people committed to rebuilding the Temple, they faced a harsh economic reality marked by a painful gap between their expectations and their actual harvest. The primary approach among commentators is that God brought a curse upon the agriculture of the time, causing the crops to dry up, shrink, and yield significantly less than anticipated [רד״ק, ביאור שטיינזלץ].
A farmer would approach a heap of wheat fully expecting it to produce twenty measures of grain, only to discover a mere ten. These numbers are not necessarily exact, but rather illustrate a devastating loss of roughly half the expected crop [רד״ק].
This agricultural ruin extended to wine production as well. A person would go down to the wine vat—the pit where the juice flows from the press [רש״י, מצודת ציון]—intending to draw out the liquid. While some understand the specific descriptions of this process as referring to the winepress itself or the physical act of treading the grapes [מצודת ציון, רד״ק], others explain it refers to a standard, familiar unit of measurement for drawing wine, similar to a jug [רש״י, מלבי״ם, רד״ק]. Regardless of the exact method, the farmer would expect to draw fifty measures of wine, yet would find only twenty.
A noticeable difference exists in the rate of loss between the grain and the wine. While the grain was reduced by half, the wine suffered a proportionally greater loss. This discrepancy does not mean that God sent a more severe curse upon the vineyard. Instead, the difference stems from how a farmer estimates the yield. A heap of grain sits out in the open and is relatively easy to assess visually. Wine, however, collects in a deep, hidden pit, leading a person to easily misjudge the volume and inflate their expectations [רש״י]. Furthermore, wine is naturally processed and measured in larger quantities. When such an important agricultural staple falls short, it serves as a particularly harsh and troubling sign for the world [רש״י].