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Jehoshaphat was loyal to his fellow believers in Yahweh, even toward a king who was weak and obviously backslidden.

Perhaps Jehoshaphat wasn't certain about the prophecy -- only one prophet had declared defeat and death, after all. Prophecy needs discernment and, perhaps, interpretation. It doesn't appear that Jehoshaphat had circumstantial validation of the prophecy, or other sorts of validation. A similar unsureness happens often when we hear what we think is God's voice in our inner ear, or even hear a contemporary prophecy.  At this point, we test and make certain about what we hear. Jehoshaphat didn't do this.

I disagree with your assessment of him. In my opinion, Jehoshaphat had a strong character. He was loyal. He got rid of the traces of Asherah (though he left some of the high places) -- perhaps he was being politically expedient? His heart was "set on seeking God," ... and he "did what was right in the eyes of the Lord ..." 

He did what was right in God's eyes. That's remarkable. When it was time to go to war, he did the right thing by going to war. Note that warring wasn't condemned, only Ahab who was condemned for things done before that war commenced. God called many men in the OT to be fighters, commanders and savvy strategists just as He calls men today. Jehoshaphat was one of those called to war by God Himself.

The two prophecies (I Kings 22 and 2 Chron 19) seem to conflict: in the first, Jehoshaphat is described as doing right in God's eyes except for not removing the high places; in the second, Jehoshaphat is condemned for helping the wicked and praised for removing traces of idol worship.

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Q24. I wonder was Jehoshaphat afraid and at the same time in awe of Ahab? In 1 Kings 22 v 4 when Ahab asks Jehoshaphat if he will fight with him to regain Ramoth Gilead his answer is “ I am as you are, my people as your people, my horses as your horses.”  This doesn’t sound like a very ‘Kingly’ answer, he appears to be subservient to Ahab. Maybe he was a weak man. Maybe Jehoshaphat trusted God so much that he thought if he did go to war with Ahab out of loyalty that Yahweh would protect him and his men. Maybe he was afraid of the consequences if he said he was not going to go to war.  There had been no war between Aran and Israel for three years, I would have thought Jehoshaphat should have been advising Ahab to leave well alone and not be putting the lives of his men at risk with an unnecessary war. Maybe I am looking at it with twenty first century eyes. Maybe Jehoshaphat thought he could influence Ahab to return to Yahweh. He was certainly brave enough to ask Ahab to send for a prophet of God. 

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Q24(1,Kings22:29;2Chronicles19:2)Why do you think Jehoshaphat goes in to battle alongside Ahab,even after he hears Micaiahs

kind of weakness in Jehoshafat character does this  decision suggest?

Loyalty is what made Jehoshaphat to agree to help the king.

I think maybe Jehoshaphat was having having strong faith to God that he will protect him to his enemies. 

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Q24. (1 Kings 22:29; 2 Chronicles 19:2) 
Why do you think Jehoshaphat goes into battle alongside Ahab, even after he hears Micaiah's prophecy? What kind of weaknesses in Jehoshaphat's character does this decision suggest? 
It’s difficult to understand why Jehoshaphat, who was a godly king who worshipped Yahweh; who even after hearing Micaiah’s prophecy, still goes into battle with Ahab. He had heard that Israel would lose the battle and that Ahab would die. Yet he carries on this alliance with Ahab and joins him in battle. He must have known all about Ahab’s and Jezebel’s Baal worship and evil deeds, which had led Israel astray and away from the Lord. Him being a godly leader, should have known better than forming an alliance with such pagan worshippers. Could it be a moment of weakness, or lack of discernment? Then again, perhaps he might have had in mind to unite both Judah and Israel under the true God. Seeing himself as being the one who would be able to achieve this. Maybe the fact that his son, Jehoram was married to Ahab’s daughter, Athaliah, had something to do with it. However, on his return to Judah he was rebuked for this ungodly relationship with Ahab. He must have repented and recognised the error of his ways. 
 

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Q24. (1 Kings 22:29; 2 Chronicles 19:2)

Why do you think Jehoshaphat goes into battle alongside Ahab, even after he hears Micaiah's prophecy?

What kind of weaknesses in Jehoshaphat's character does this decision suggest?

Jehoshaphat had promised to go into battle with Ahab and then he asked for a prophet's message.  So to stick to his word he continues and goes into battle.  No 1 there should never have been a marriage between his son and the daughter of Ahab. That is where the problem started.  Now he felt compelled to help his son''s father-in-law. 

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Jehoshaphat joins Ahab's army by going into battle along with them, even though he heard the prophetic message from Micaiah. Perhaps, Jehoshaphat joined Ahab in battle because he did not want to appear weak as a leader. After all in kings 22:2-4 King Ahab of Israel ask King Jehoshaphat of Judah to join him in a battle at Ramoth Gilead which was under Syrian control. Jehoshaphat replied "I'am as you are, my people as your people, my horse as your horse". This would also strengthen the relations between Judah and Isreal.

         

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Q24. (1 Kings 22:29; 2 Chronicles 19:2) Why do you think Jehoshaphat goes into battle alongside Ahab, even after he hears Micaiah's prophecy? What kind of weaknesses in Jehoshaphat's character does this decision suggest?

May be King Jehoshaphat still went along to fight with King Ahab despite the prophecy that he would return alive from the war because of brotherly love. But it could also be weakness that some of us exhibit and cannot be bold enough to say no when the need to say so arises.
 

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Happiness is proportionate to completeness of consecration.  Jehosophat wanted to be a buddy to Ahab.   This is how Christains get into trouble.   They have not renounced the world, the flesh and the devil fully.  The persuasions of the wicked are subtle.  Jehosophat should have regarded the Prophet Micaiah's prophecy with utmost importance, but he joined forces with Ahab anyway.

Jehosophat had an element of "people pleasing" in his character.  There was definitely a conflict of interests here.  Without the Holy Spirit and a complete Bible, we read how many under the Old Covenant were so confused.   Gideon fell into superstitious worship when he built a shrine for a vestments used in worship. Disobedience provokes the judgments of God.   We see this demise in the life of King Saul; Kings Solomon and Mannasah as well.

Jehosophat had no recourse to the Urim and Thummin as in the days of Moses and Joshua.   Jehosophat did not pray about this war seriously enough.   He was sumptuously entertained by Ahab; he mostly would be concerned what his political partners from Judah would say.   This is definitely a case that illustrates the neglect of private prayer.  No indication of Jehosophat consulting the High Priest.   Where was Obadiah, the court Manger of Ahab?   Obadiah was a godly man

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Q24. (1 Kings 22:29; 2 Chronicles 19:2) Why do you think Jehoshaphat goes into battle alongside Ahab, even after he hears Micaiah's prophecy? What kind of weaknesses in Jehoshaphat's character does this decision suggest?King Jehoshaphat went to battle alongside Ahab and because of his love for his son father in law and for the Israelites even after he heard Micaiah's prophecy. 

The weaknesses in king Jehoshaphat is his love for God and humanity. 

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Why do you think Jehoshaphat goes into battle alongside Ahab, even after he hears Micaiah’s prophecy?

Jehoshaphat made a promise and he was loyal to that promise.

What kind of weaknesses in Jehoshaphat’s character does this decision suggest?

Jehoshaphat's weakness came from surrounding himself with wicked people.  Even though he knew Ahab was setting him up to be killed, he went along with with it.

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Q24. Why did Jehoshaphat went to war with  king Ahaz even after hearing Micaiah prophecy?

I think because king Ahab did not believe Micaiah's prophecy,  so he did not take it serious that Ahab will not make it in the battle and came along to support him

24.1 What kind of Jehoshaphat weakness in character  does this decision  suggest?

When you surround yourself with people who speak and do evil , even when something  good comes  you will not see

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