A Stealthy Approach

I’ve never seen an entire party reliably stealth during a campaign. Getting four to six players to all make a d20 roll means that statistically someone is going to roll ass. And with so many different skill levels at work there’s going to be some characters that are completely silent and others that sound like a marching band squishing into a single 5-foot space. At best it works by splitting the party and having a single scout 10 to 30 feet ahead, quietly avoiding combat. But getting a surprise is still tricky without leaving a character behind and having them spend the first round or two rushing into range.

Optional rules in 3e and 4e both tried to skirt around this with various group checks, so that as long as the majority of people succeeded on the skill challenge or complex skill check then the group as a whole succeeded. Which works in play but seems odd in narrating, as four people being super stealthy doesn’t magically negate the person stepping in the bucket and clumsily flailing around, or three people succeeding on a climb check doesn’t halt the fall of the couple who failed. Skilled DM narration can help somewhat. A really good success in a climb check could also mean the character is able to cancel a failure, catching a falling party member or helping them up. But, really, everyone should still be required to roll at least one successful check.