Deception 4 

((I used my inspiration to gain advantage on the roll))

Wow! and Ugh!

Devin mutters to himself “If Jaylen was still here, I’m sure she be better at this than me but here goes” undeterred he keeps riding towards where the Giant is approaching from yelling out his warning. Whether the Giant – which Devin can tell is a Fire Giant – may have already been suspicious, Devin will never know but his warning seems to be sufficient and the Giant turns around and starts heading back the way it came.

Ilezenya calls on his innate powers of darkness and is able to block the view of six of the guards manning the battlements. Lukian takes advantage of Ilezenya’s darkness and targets the left end of the battle line (DC13 - 10, roll]1d20[/roll], 17, roll]1d20[/roll]) covering two of the guards in flame.

DM rolls 

 Ebonitus you're doing what?

Ebonitus sees that things are starting to heat up, so he also targets one of the guards he can see, the leftmost one, and stretching his fingers directs a guiding bolt in his direction.

Attack: 16 Damage: 10 radiant damage

On a hit, the next attack has advantage.

Despite the fact that the guard is hiding behind the battlements Ebonitus still manages to hit him.

D.O.R.K. do you want to do anything?

(@Grant: Nothing really she'd want to do atm other than make sure horse go fast(ie Dash), which I assume takes an action. If not, she'll take the Dodge Action if possible, but otherwise stay focused on closing the distance with the city defenders.)

The four guards who have visibility to the party take another series of shots at (1 = D.O.R.K, 2 = Ebonitus, 3 = Ilzenya, 4 = Lukian) {3, 1, 3, 4}  with the following impact

D.O.R.K.
Attack: 10 Damage: 2

Ebonitus
Attack: 17 Damage: 2
Attack: 5 Damage: 9

Ilzenya
Attack: 3 Damage: 5

Meanwhile from his point on the south gate where he had been planning on meeting with the fire giant, Nelgorn curses and a bolt of black and red light flashes out targeting Devin (Attack: 7 Damage: 17)

And back to party

Ilezenya continues to move closer to the walls (now at 50'), keeping behind the cover of his sphere of darkness. He will target Nelgorn when he targets Devin, a flash of golden light to counter Nelgorn's darker mix. Attack: 15 Damage: 18 (On a hit, the next attack roll made against this target before the end of Ilezenya's next turn has advantage, thanks to the mystical dim light glittering on the target until then.)

A point of clarification - D.O.R.K., Ebonitus, Ilezenya and Lukian are approaching the Western gate while Devin took off at a tangent to warn the Fire Giant approaching the southern gate and that's where he was fired upon.

I'm assuming therefore that Ilezenya was trying to blast one of the guards on the wall who has been firing at the party. However just as the flash of golden light hits the wall the guard ducks behind a crenelation and the dhot misses.

(Roger on the guard as target - bummer on missing!)

D.O.R.K remains, if nothing else, relentless in her pursuit of closing the distance. So, once either at the wall perimeters, or through a gateway they couldn't quite be sealed completely, the construct either dismounts to try and scale the walls through any breaks within it(or making some of her own), or as soon as she's past the perimeter on horseback, it is time for her to turn about and let rain some holy artillery!

If there is an opening:;

Action: Cast (Cantrip)Holy Artillery at archer, inflicting 13 Radiant Damage. Dex Save(DC 14) for No Damage. (Spell ignores partial cover bonuses)

If there is no gateway/gateway closed:

Action: Attempt to scale wall for 19.

(@Grant: The above is also contingent on me math being right. Which by my record, we should be about 30ft away from the wall at the start of this turn. At least those that were able to keep dashing with the horse.)

Devin grins as the giant turns away from the city.  Mission accomplished it seems. If he can't spy on the meeting at least he can stop it.

He quick ducks as the black and red flash of light zips past him and he turns his attention to the new threat.  He then sends 5 bolts of light that slam into the man.

Magic Missile lvl 3

17 force damage

(@DM I assume that the 20 was a hit for 4 Points damage)

Ebonitus continues towards the West gate as fast as his horse can carry him. Slowing down marginally to take a shot at the guard he previously hit (who is glowing faintly from the previous successful guiding bolt). Guiding Bolt

Attack: 24 Damage: 13 radiant damage - and the next attack on this target has advantage on a successful hit.

If there is an opening:;

Action: Cast (Cantrip)Holy Artillery at archer, inflicting 13 Radiant Damage. Dex Save(DC 14) for No Damage. (Spell ignores partial cover bonuses)

If there is no gateway/gateway closed:

Action: Attempt to scale wall for 19.

D.O.R.K. as you approached the ruined walls you could see that where the gate once stood an opening now existed. However as it was the centre of the defence it is now hidden by Ilezenya's globe of darkness. 

Which side of the wall are you seeking to scale that the guards are behind the crenelations at the top of the wall which is about 30 feet high. 

(@DM: Side facing the outside, but otherwise same general section of wall that the guards were firing from atop of.)

Is Lukian doing anything 

Lukian is cursing the fact that they may never know the purpose of the clandestine meeting. He picks three of the guards he can see and calls out another quick phrase in Elvish. Three rays of light shoot from his palm at the guards.

Scorching ray 1: Attack: 21 Damage: 5 fire damage

Scorching ray 2: Attack: 11 Damage: 10 fire damage

Scorching ray 3: Attack: 8 Damage: 8 fire damage

A city under siege by an overpowering force?

A bucketload of DM rolls and other things

As a result of the party's fire on the guards manning the wall two give gurgled cries and collapse over the side of the wall. Seeing D.O.R.K. approach the base of the wall and getting ready to scale it, the remaining 8 guards move out of Ilezenya's area of darkness in order to shoot at the immediate threat.

Guard #3 - Attack: 13 Damage: 9

Guard #4 - Attack: 4 Damage: 3

Guard #5 - Attack: 19 Damage: 9

Guard #6 - Attack: 6 Damage: 4

Guard #7 - Attack: 20 Damage: 4

Guard #8 - Attack: 13 Damage: 1

Guard #9 - Attack: 23 Damage: 6

Guard #10 - Attack: 18 Damage: 8

From somewhere down near the south gate Devin hears a curse as his Magic missiles hit Nelgarn who quickly ducks out of sight {6}

Meanwhile the three guards who were with him launch crossbow bolts at Devin

Guard #11 - Attack: 16 Damage: 4

Guard #12 - Attack: 10 Damage: 6

Guard #13 - Attack: 16 Damage: 6 {36

D.O.R.K. cant use her shield while trying to scale the wall and takes 15 HP of damage from several crossbow bolts. Undaunted she continues to climb and will get to the battlements at the end of next round.

Devin gets hit by two crossbow bolts for 17 HP of damage.

Devin, Ebonitus, Ilezenya and Lukian - what are you doing as its now the next round ? 
(OOC for simplicity i'm not rolling initiative and simply letting the party go first)

(OOC: If I remember correctly, Warding Bond should still be active between D.O.R.K. and Ebonitus (1 hour - 60 feet) - so we should take half damage each.)

Ebonitus moves close to the wall and dismounts so he can remain near D.O.R.K. As the guards lean over to fire upon D.O.R.K. Ebonitus casts Spiritual weapon and a large hammer appears above the parapets, striking the first guard to show his head to take a shot at D.O.R.K.

Attack: 16 Damage: 14 force damage

As a bonus action (if I get a bonus action) Ebonitus will also move the hammer and hit the next guard (which could be the same one) to show his head.

Attack: 15 Damage: 5

 (@Grant: I assume then as part of beginning her ascent, D.O.R.K would've had to doff her shield, so updated the sheet to include that and warding bond bonus. Though, this didn't change which attacks hit, and only split the damage so both Ebon and D.O.R.K took 7 damage each.)

(@Whatwall: As part of casting the spell, which is a bonus action in itself, you can attack someone with spiritual weapon. But you can't, barring DM homebrewing, use an action to attack again with it.)

Warding bond only lasts an hour when did you cast it?