A voice of comfort and news of redemption breaks through the darkness, calling out to Jerusalem to wake from a long slumber of suffering and pain. The period of punishment has finally come to an end. The imagery paints a picture of someone who has become intoxicated from a bitter drink, fallen into a deep sleep, and is now being summoned to wake up to a new, sober reality.
The double call to awaken and rise is meant to rouse the nation from the heavy sleep of the Exile and its sorrow [מצודת דוד, מצודת ציון]. This repetition also hints that the oaths God placed upon Israel—warning them not to force the end of days or awaken the redemption prematurely—have now expired [אהבת יהונתן]. By directly addressing Jerusalem, the message emphasizes that the awakening and the redemption now depend entirely on her and her own actions [מלבי״ם]. Jerusalem is likened to a person who drank heavily from a cup of wrath, collapsed into a deep sleep, and must now finally stand up [אבן עזרא].
Having suffered the full weight of divine anger and the bitterness of the Exile, Jerusalem has completely cleansed her past sins [מצודת דוד, צאינה וראינה]. The nature of this bitter drink is explored through various interpretations. The primary approach among commentators is that the text refers to the bitter dregs that settle and become fixed at the very bottom of a cup. However, others explain it as a large goblet [שד״ל, ביאור שטיינזלץ]. In this view, a central cup of wrath was passed around among the guests, and each person filled their own personal goblet from it [שד״ל]. The drink itself is understood either as a deadly poison that brings about fear and violent trembling [רד״ק, שד״ל, אבן עזרא], or as a brew that dulls the heart, drains a person's strength, and leaves them feeling entirely bound and helpless [רש״י, מצודת ציון].
The act of draining this drink down to the last drop serves as a powerful metaphor. Sucking out the very dregs of the cup signifies that Jerusalem has absorbed every ounce of the suffering decreed upon her during the Exile. Because not a single drop remains, all the intended hardships have already come to pass, the past sins are fully repaired, and no further disaster will strike her [מצודת דוד, רד״ק, צאינה וראינה].
Looking deeper into this punishment, there is a distinction between two different aspects of the suffering. The cup of wrath represents God's anger and the hiding of His face. Israel did not have to drink this cup in its entirety, as God never abandoned them completely. In contrast, the cup of trembling represents the actual physical punishment and suffering of the Exile, which they were forced to drink and drain completely [מלבי״ם]. Finally, the act of drinking the bitter dregs down to the very end serves as a historical correction for ancient wrongs. It acts as a repair for the sin of the Tree of Knowledge, which is traditionally associated with squeezing grapes and drinking their dregs. Now that this ancient sin has been fully corrected, Jerusalem is finally free to rise and be redeemed [אהבת יהונתן].