So after resting in a nearby structure, you notice the raiders haven't completely locked down the area around the keep and you could still make it through the gate. 

There are a few different ways you could get past them. What would you like to do?

"Perhaps we should sneak in this time?"

stealth- 22?

"Always stealth." I will keep to the shadows. 13

"I may as well try to be quiet." 18

Alright you see a group of 6 Kobolds and 4 Cultists. They don't seem to now you are there. They are just moving through the streets at the moment not harassing anyone yet. One of the Kobolds notably has wings.

As the "tactical character" Murmur will point out we should strike while we have the element of surprise.

If you all want to attack, each of you tell me what you want to do. Alternatively if you don't plan to attack tell me what you'd do.

I'm okay with chucking a Chromatic Orb at the winged one.

I would shoot a cultist. I don't know what they can do and I don't want to find out.

I would run up to the group and attack 2 of the Kobolds from hiding.

Okay, let's get initiatives then.

Kobolds 1-5 7

Winged Kobold 5

Cultist 1-4 3

Jarvroth 4

20 for Fiva

Murmur will get 14

So Fiva then Murmur, Kobolds 1-5, then the cultists, the winged Kobold then Jarvrith.

They are all surprised so you have advantage in your first attack against each.

Fiva you're up and about 30ft. from them.

I'll use my Shortbow to shoot Cultist 1 8 for 6

The arrow flies over his shoulder but you are still hidden.

Murmur, you're up.

I will attack Kobold 1 with my Shortsword 23 dealing 4

Then Kobold 2 with my Shortsword 8 dealing 7

Kobold 1 is struck down with a whimper, but the other's armor absorbs the hit.

Jarvroth you turn.

Chromatic Orb 24 for 12 thunder, plus 17 for the crit.