D&D 5E Surprise and when to roll initiative?

[Punchycal]

Hello, I have recently started playing 5th edition dnd and am enjoying it immensely (it's the first time I've played dnd but I've played warhammer quest a lot back in the day so our adventures so far have been mostly hack and slash orientated) I am playing a elf fighter and my friend is a human cleric and a bard. Anyway this is what I'm struggling to get to grips with:

I approach a door at the end of a corridor and declare that I'm moving stealthily (my character has Dex 20 and the stealth skill from his background as an urchin so a handy +7 to the roll) I then carefully open the door slightly and take a peak to see what lies beyond it. The room contains three skeletons. Using my longbow I declare I will take a shot at one of them. Now the skeletons haven't noticed us so to my mind they should be surprised when combat begins, but the way we've been playing is just roll initiative and combat begins. So my question to you experienced DMs is how would you proceed from this point onwards?
Should the elf shoot out of sequence then initiative is rolled or what?
Also at what range would you say the skellies should have a chance of passively perceiving the cleric clanking along in his chainmail?

We play on a grid using dungeon tiles btw, I hope this makes sense as I'm not used to posting on forums

 

[Valador]

The DM would have determined when to check your stealth versus their passive perception to notice you. I would have said no later than when you opened the door, check perception, depending on how much noise everyone else was making.

In this situation as soon as you declare a hostile action you roll initiative. The DM determines who's surprised and who isn't. Anything surprised cannot act on their first turn of combat, but can only react after their first turn. Follow initiative order to resolve actions, combat as usual.

Combat only takes place inside the turns of combat.

You can probably find some good info in this thread here.
http://www.enworld.org/forum/showthread.php?466595-When-to-Roll-Initiative

Welcome to the forums!

 

[Punchycal]

I see so if any party member rolled less than the skellies passive perception score for their stealth check, then they would be alerted to our presence and hence no surprise yes? Would it be fair to say none of the PCs would be surprised as the elf tells them there are enemies in the room ahead? Sorry if this sounds a bit like splitting hairs, and thx for your help.

 

[jodyjohnson]

It would be reasonable to use the group skill checks rule if the group as a whole is trying to be stealthy (half success or better).

 

[iserith]

I see so if any party member rolled less than the skellies passive perception score for their stealth check, then they would be alerted to our presence and hence no surprise yes?

Yes, but as [MENTION=5590]jodyjohnson[/MENTION] notes, a group Stealth check is good for a situation in which the party is cooperating to sneak around and the outcome of that effort is uncertain.

Would it be fair to say none of the PCs would be surprised as the elf tells them there are enemies in the room ahead?

Yes, that's fair. You can't be surprised if you're aware of the threat.

Sorry if this sounds a bit like splitting hairs, and thx for your help.

You're welcome and I think it's important to note that a lot of this is going to come down to DM calls which may vary from situation to situation depending on the context of the scene that is unfolding.

 

[Horwath]

It would be reasonable to use the group skill checks rule if the group as a whole is trying to be stealthy (half success or better).

No.

There is a reason why you do not bring mobile tank to stealth missions.

 

[Celtavian]

This might go down the rabbit hole again if we start discussing when surprise ends.