In the Book of Jeremiah
Zedekiah's first appearance in the Book of Jeremiah is in Jeremiah 21, where he sends Pashhur, the son of Malchiah, and the priest Zephaniah, son of Maaseiah, to the prophet Jeremiah to ask God why Nebuchadnezzar had declared war against Judah; they suspected that God was going to make Nebuchadnezzar withdraw from besieging them. Jeremiah responds to Pashhur and Zephaniah and tells them that God declares what will happen if Zedekiah does not surrender to Nebuchadnezzar—his people will die by the sword, pestilence, and famine, but if he surrenders they will survive. In Jeremiah 22, Jeremiah advises Zedekiah to act with justice and righteousness and warns him what will happen if he does not obey God's word. (Jeremiah 21:1–9, 22:1–7) In Jeremiah 24, God shows Jeremiah a vision of two baskets of figs placed before a temple, one filled with good, ripe figs, and the other filled with bad figs. God compares Zedekiah and his officials to the bad figs and states that they will be destroyed by sword, famine, and pestilence. Jeremiah had previously advised Zedekiah at the beginning of his reign to submit to Babylon and to not listen to false prophets like Hananiah who prophesied that he would not have to serve Babylon. (24)
In Zedekiah's tenth year, he imprisons Jeremiah in his palace because Jeremiah had prophesied that Jerusalem would be captured by Nebuchadnezzar. Subsequently, Jeremiah prophesies that Zedekiah will die in peace and have a traditional funeral like the kings before him, but he will be captured by Babylon. Later, Zedekiah made a covenant with his people to free all Hebrew slaves, but they were re-enslaved by their captors. God speaks through Jeremiah and notes that Zedekiah did what was right by freeing the Hebrew slaves, but he broke his own covenant by allowing them to be re-enslaved. (34) Zedekiah sends Jehucal, the son of Shelemiah, and Zephaniah the priest to ask Jeremiah to pray for them when Apries's army had threatened the Babylonians enough to retreat from sieging Jerusalem. Jeremiah once again responds that the Babylonians will come back and capture the city.
Previously, when Jeremiah had been imprisoned in the house of Jonathan the secretary in suspicion that he was defecting to the Babylonians, Zedekiah secretly questioned him and asked if there was any word from God, to which Jeremiah responded that there was, that Zedekiah will be captured by Nebuchadnezzar. Jeremiah pleads that he will die if he is sent back to Jonathan's house so Zedekiah transferred him to the court of the guard and ordered that a loaf of bread be given to him daily. Zedekiah refuses his officials' pleas to execute Jeremiah for his prophecies and instead lets them do what they want with Jeremiah, that is throwing him into a cistern belonging to Zedekiah's son Malchiah. Ebed-melech, a servant, heard this and went to Zedekiah (who was at the Benjamin Gate) to tell him that Jeremiah would die if he was not saved from the pit. Zedekiah commanded Ebed-melech to take thirty-men to lift Jeremiah from the cistern. Jeremiah then warns Zedekiah again that he shall be spared if he obeys God and surrenders to Babylon, but if he does not Jerusalem will be destroyed and he will not escape from Nebuchadnezzar.