"You got it!" Cage unslings his cannon from his back and waits for the countdown.

Kekro holds his spear tight amd grins. You can feel his excitement radiate.

“Our heroes prepared for to get their first taste of the crackling caverns”

Fred tips his hat and notes his readiness.  "Let's do this.."

Aiming for the element of stealth and surprise, Alend whispers that the party should go on 3 and counts up using his fingers.

Darting around the corner to attack when he reaches 3.  (@DM Let us know if a further Stealth check is needed to achieve surprise.)

“Our heroes ran out with as much stealth as possible would they succeed”

{{Will we have a representation of the battlefield? Not asking for a battle map really, a blank grid would do}}

Initiative? 12

Initiative: 18
stealth: 26 (if required)

Red fred begins his sneaking, still with his detect magic up (lasts for 10 minutes)

stealth 18

initiative 6

Alend darts in low and wide, sticking to the shadows to the extent possible.

Stealth:  Due to Rogues' Reliable Talent, Take higher number out of 23 and 26 
Initiative:  25 

Quote from Tybard >>

Alend darts in low and wide, sticking to the shadows to the extent possible.

Stealth:  Due to Rogues' Reliable Talent, Take higher number out of 23 and 30 
Initiative:  12 

So Stealth 30 and Initiative 12.

I am going to assume unless I hear otherwise that Alend's owl familiar (Shiv) also acts on his turn.

The owl would move along side alend and for those who wonder the owl could…

Quote from Griffinb13 >>

The owl would move along side alend and for those who wonder the owl could…

Just to set expectations, in combat, Shiv the owl is usually going to fly up to the enemy (60' fly speed), take the help action to give Alend advantage on 1 attack that round, then fly back to his shoulder most of the time, using owl's Flyby feature to NOT provoke opportunity attacks when it flies out of reach.  I would flavor this as flapping its wings, hooting behind the target's head, pooping on them, etc.

"A familiar can't attack, but it can take other actions as normal." (including the help action.)

This is in addition to any out-of-combat scouting that might require flying of course...

The aberration doesn’t notice Alend and his owl

Who acts first in initiative?  I think Kekro is first among the PCs with a 14, then Alend/Cage, the Red Fred.

Did our Stealth get us all a surprise round?  Or only Alend/owl?

{{I think the owl gets its own initiative}}

Quote from Treewy >>

{{I think the owl gets its own initiative}}

Yep - that's what it says in the spell description for Find Familiar.  I've just seen all my DMs just have the familiar go on the same initiative as the character.  That's why I was leaving it up to Griffinb13.  I'm good either way.

If we need the owl's initiative, here it is:  17 

Do to the nature of what the creatures doing he’ll go on your turn 

(OOC:  Should we go ahead and take our actions in initiative order?  Do we get a round where the aberrations are surprised?)