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<blockquote data-quote="Jon Gilliam" data-source="post: 8037388" data-attributes="member: 6920404">The 5e concept of surprise springs from the idea of an ambush : something that the party decides to do together in unison.&nbsp; For example, PHB p. 189 : &quot;A band of adventures sneaks up on a bandit camp, springing from the trees to attack them.&quot;&nbsp; I'm well aware that surprise is something experienced by the target, and if you're just pointing out inexact language used in my discussion, that's fine.&nbsp; I thought it was clear what I was saying : if one side has an unhidden member at the start of combat (assassin or not), the party has no chance of surprising any of their opponents.In your scenario, Alice is setup fine.&nbsp; Bob probably is hidden also, as he's taking advantage of an edge case to hide among a crowd, although the DM would decide that (see errata for the PHB under Hiding where the DM decides circumstance appropriate for hiding).&nbsp; However, Bob does not spoil surprise (see if you like that language) because he is disguised, but rather because he is hidden due to Charlie being (at the DM's discretion) distracted by all of the other orchestra member's around him, covered by the Hiding side-bar on p. 177 of the PHB:If Bob is only disguised but not hidden, surprise is spoiled because the rules provide no mechanism for resolving surprise on anything other than passive Perception versus Stealth.&nbsp; You're making up rules on the spot (which can be fine, but it's not rules as written) if you're deciding surprise based on Insight versus Deception, or whatever other check might be appropriate to Bob's disguise.</blockquote>

[QUOTE="Jon Gilliam, post: 8037388, member: 6920404"] The 5e concept of surprise springs from the idea of an ambush : something that the party decides to do together in unison. For example, PHB p. 189 : "A band of adventures sneaks up on a bandit camp, springing from the trees to attack them." I'm well aware that surprise is something experienced by the target, and if you're just pointing out inexact language used in my discussion, that's fine. I thought it was clear what I was saying : if one side has an unhidden member at the start of combat (assassin or not), the party has no chance of surprising any of their opponents. In your scenario, Alice is setup fine. Bob probably is hidden also, as he's taking advantage of an edge case to hide among a crowd, although the DM would decide that (see errata for the PHB under Hiding where the DM decides circumstance appropriate for hiding). However, Bob does not spoil surprise (see if you like that language) because he is disguised, but rather because he is hidden due to Charlie being (at the DM's discretion) distracted by all of the other orchestra member's around him, covered by the Hiding side-bar on p. 177 of the PHB: If Bob is only disguised but not hidden, surprise is spoiled because the rules provide no mechanism for resolving surprise on anything other than passive Perception versus Stealth. You're making up rules on the spot (which can be fine, but it's not rules as written) if you're deciding surprise based on Insight versus Deception, or whatever other check might be appropriate to Bob's disguise. [/QUOTE]

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