Receive note in the middle of the night, quote "Want to be a part of something big? Speak to Davil Starsong at the Yawning Portal. Come alone."
One mission from witch is to find Halam in Waterdeep mountain. However, Amon would rather find the horse first. Issechar wants to do the latter due to being near the Yawning Portal.
Found talking mare by sending out crane to then followed by Paal's owl. We find them and to get them alone, Issechar casts Disguise Self as Captain of the Guard to get cart driver away from cart.
Goes to the Yawning Portal alone about Davil Starsong. Learns about this opportunity, working with this faction as a spy with the two of them. It is an enticing offer and Issechar is hungry for larger opportunities, and truthfully doesn't know group too well to dedicate himself to them. Seriously considers this and stays noticeably quiet the rest of the adventure. Thinking. He will be back at Yawning Portal within the next 5 days to give an answer.
On his way out of the Yawning Portal, he sees 3-strings take the stage. He casts Vicious Mockery as a joke but causes actual psychic damage. 3-Strings passes out and Issechar tries to get out stealthily, but he is stopped by the bar owner. Issechar talks his way out of hit by insisting that the item that he created via prestidigitation in his hand was not stollen from three strings as it has his name on it. (He made this object to keep up the rouse to his team that he needed something from Three-Strings) and that Three-Strings passed out via dehydration from drinking. Is able to convince him but told to keep his personal conflicts out of the bar. Issechar understands.
Goes to the mountain to find Halam. Runs into two cockatrices, both of which you damage and one kill. This is notably, the first time Issechar has ever taken the life of someone with a weapon. Issechar considers this further, feeling a thrill in this, like the sword is an extension of him, but thinks of his goals and what what they would yield to, and still finds himself thinking about Davil's offer.
When they find Halam, he says: "Evil's twin hides its face. Expect a change by winter's end. It is looking to be a gray year." through wind reading.
On way out, joins Byron and Paal in trying to take the three cockatrice chicks. Attempt to calm with a song/lullaby, and while it starts off strong, it quickly cracks out of guilt of brutally killing their mother. Eventually takes the sleeping one