Rather than playing out the entire battle in initiative order, I'm gonna have each of you roll an ability check, attack roll, and saving throw of your choice. The DC of these checks depend of which of the following rolls you decide to fill.

Take Refuge With The Non-Combatants (DC 5): The safest option, but also the least respected one when it comes to those who pick it despite being able to fight. Those who pick this option can expect to be looked down on by everyone else unless they are in no condition to fight.

Serve As The Last Line Of Defense (DC 10): The bare minimum those who can fight are expected to contribute. You'll win no glory here, but you'll be as safe as you can be while avoiding any scorn those who refuse to help would receive.

Go Where You're Needed Most (DC 15): Rather than head straight to the front lines, you can instead hang back for a time and then go relive the defenders that are being hit the hardest by the attacking forces. Not as glorious as being in the thick of it from the get go, but still better than staying in the back for the entire battle.

Head To The Front (DC 20): Get stuck in right away. Not the safest of options, but you'll have plenty of opportunities to distinguish yourself on the battlefield here.

Lead The Charge (DC 25): Someone has to go first. If that someone is you, you can expect to find yourself in a pretty precarious position. But on the bight side, the front of the front is also a pretty well respected position too.

Take Them On Alone (DC 30): Break from the rest of the defenders and hack your way into the attacking forces alone. This will most likely get you killed, but you will be remembered as a hero who gave their life to strike a grievous blow against the enemy. And if you somehow beat the odds and survive, expect to be revered by your fellows when the battle is over.

If you fail one roll, you take 1d10 battle damage. If you fail two rolls, you take 2d10 battle damage. And if you fail all three, you take 4d10 battle damage.

Because of the strategic intelligence gathered from Hawk's spying, you get a +4 to all of your rolls. Those of you with spell slots can choose to expend those spell slots to convey additional bonuses equal to the spell slot's level to yourself and/or other party members. You can do this as many times as you like so long as you have the spell slots for it.

@Lurking Krog, since the attackers are actively gunning for him, Jørmund will find the battle to be especially dangerous. As a result, his rolls will be made with disadvantage

Once the battle rolls are resolved, a standard combat encounter will then take place.

Jørmund used healing word on the two highway men allies to get them back on their feet.

Yosef spits fire at Jørmund, dealing 11 points of fire damage.

Roll for Initiative.

Map (The password is 'Highway Finale'.)

Battlefield: 20
Cascade: 18 <-
Aura: 17
Ervdul: 9
Yosef: 8
Jørmund: 5
Flicker: 3

Move: 15 feet behind Jormund, after using action, move 10 feet.
Action: Lay on Hands on Jormund. Used all of the pool to heal him 15 HP.

Ervdul moves through the right flank and frees up eight soldiers, six to push back the warforged and two to assist Yosef.

Yosef attacks Jørmund and Cascade. He hits Jørmund with a Natural 20, dealing 4 damage, and misses Cascade with a 5.

Map (The password is 'Highway Finale'.)

Battlefield: 20
Cascade: 18
Aura: 17
Ervdul: 9
Yosef: 8
Jørmund: 5 <-
Flicker: 3

Jørmund cast magic weapon with his bonus action, which is concentration.

He also attacks with his mace, which is a17 to hit. Total of 6 damage if it hits.

Flicker moves 20 feet to between Cascade and Jormund.
Attack = 5
Attack advantage = 20 (not natural)
Attack damage = 5 slashing damage

Two attackers attempt to attack Jørmund and Cascade. They both miss with a 12 and a 15.

Map (The password is 'Highway Finale'.)

Battlefield: 20
Cascade: 18 <-
Aura: 17
Ervdul: 9
Yosef: 8
Jørmund: 5
Flicker: 3

Movement: None
Bonus Action: Channel Divinity-Fury of the Tides
As a bonus action, you channel the powerful might of the waves to bolster your attacks for 1 minute. Once per turn for the duration, when you hit a creature with a weapon attack, you can choose to push the target 10 feet away from you. If pushed into an obstacle or another creature, the target takes bludgeoning damage equal to your Charisma modifier.

Action: Attack Yosef and push him into one of his allies.
Roll to hit: ...Natural 1 ;_;
Using Inspiration to reroll: Dirty 20
Damage with Fury of the Tides: 10 Damage total. 7 is Piercing, 3 is Bludgeoning.

Map (The password is 'Highway Finale'.)

Battlefield: 20
Cascade: 18
Aura: 17 <-
Ervdul: 9
Yosef: 8
Jørmund: 5
Flicker: 3

Ervdul takes out two highwayman and moves to join Yosef.

Yosef moves to and attacks Jørmund. He hits Jørmund with a 19, dealing 7 damage, and misses Cascade with a 4.

Map (The password is 'Highway Finale'.)

Battlefield: 20
Cascade: 18
Aura: 17
Ervdul: 9
Yosef: 8
Jørmund: 5 <-
Flicker: 3

Bonus action Heal word for =l7 total HP recovered.

Attack was a for a total of mediocre 7 damage.

Also CON save for magic weapon was another nat 20 for 22.