If the DM rules that casting teleport starts combat, they first determine surprise. In most situations however, facing someone who teleported in unexpectedly could be a Surprise. But, if they had some reason to expect the attack any minute, and knew they face spellcasters who can teleport or walk through walls, they might be extremely alert, ready for anything, and not be surprised, even if you teleport in. If they are unprepared for an attack, lounging around in their den, then they surely would be surprised to suddenly face a group of adventurers out of nowhere. If the foes are surprised depends on what they expect, not just if they can notice you. The caster's team are not surprised - they may be if they find the room empty or someone else there than they expected, but not in the capital-S Surprise sense where they are unprepared to face a threat or engage in combat. The wizard with teleport materializing suddenly° out of nothing sounds like a good fit for an "enemy with a special ability (.) that makes it extremely surprising". This expanded definition is valuable, as it shifts the focus from being able to notice a threat to the more general question if you were prepared for the threat to happen. The gelatinous cube’s Transparent trait, that makes it exceptionally You must be caught off guard, usually because you failed to notice foes being stealthy or you were startled by an enemy with a special ability, such as The Sage Advise Compendium elaborates further what is meant by "notice a threat": (.) Any character or monster that doesn’t notice a threat is surprised The DM determines who might be surprised. Who is surprised is entirely up to the DM (p. Once combat starts, you follow the rules under Combat Step by Step (PHB, p. Spellcasting such as teleport however is not necessarily a combat action. This works with standoffs, traitors, and trying to ready an action before combat (which as a combat action starts combat and avoids the issue). A good proxy to start combat is when anyone tries to take any combat action (e.g., tries to make an attack). When does combat start? The rules do not say so explicitly, so this will be for the DM to determine. The wizard cannot ready an action outside of combat, so he could not ready the teleport spell until combat has begun.
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