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The optional rule on flanking (DMG, p. 251) says:

Flanking on Squares. When a creature and at least one of its allies are adjacent to an enemy and on opposite sides or corners of the enemy's space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy.

When in doubt about whether two creatures flank an enemy on a grid, trace an imaginary line between the centers of the creatures' spaces. If the line passes through opposite sides or corners of the enemy's space, the enemy is flanked.

Flanking on Hexes. When a creature and at least one of its allies are adjacent to an enemy and on opposite sides of the enemy's space, they flank that enemy, and each of them has advantage on attack rolls against that enemy. On hexes, count around the enemy from one creature to its ally. Against a Medium or smaller creature, the allies flank if there are 2 hexes between them. Against a Large creature, the allies flank if there are 4 hexes between them. Against a Huge creature, they must have 5 hexes between them. Against a Gargantuan creature, they must have at least 6 hexes between them.

The description of the Assassin rogue's Assassinate feature (PHB, p. 97) says:

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

If I'm flanking a creature, is my attack considered a surprise attack?

Had a debate yesterday on whether or not Assassinate can be used every round or only in the first round of combat 'Surprise'. We decided or the latter. Is this correct?

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    \$\begingroup\$ First of all, welcome to the site, have a look at the tour if you haven't already. I'm curious, What made you think that flanking triggers assassinate? You mention that you came to a ruling, but I'd be curious to hear a bit of the arguments, thst may make for more in depth answers too. \$\endgroup\$ – 3C273 Jul 8 at 1:18
  • \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. Your title and the first part of your question mention flanking, but the end of your question just asks about when Assassinate can be used. Can you clarify the connection between the two, and what confuses you about flanking with regard to Assassinate? Also, rather than quoting the entire description of flanking, you should edit it to only include what's necessary/relevant to your question (e.g. what made you think it relates to surprise). \$\endgroup\$ – V2Blast Jul 8 at 2:48
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Flanking makes no difference here, it is restricted to the 1st turn

Surprise only counts at the start of the combat in D&D 5e. As we can read in the PHB about The Order of Combat on page 189:

If you're surprised, you can't move or take an action on your first turn of the combat, and you can't take a reaction until that turn ends.

The first part of Assassinate works on a creature that has not taken a turn yet. Note the wording of surprise, above: the creature still has a turn, it just cannot do anything. Thus it is limited to the first round (and also by initiative).

The second part of the feature requires the target to be surprised to grant the automatic crit, and thus will also only work in the first round.

Neither of these triggers are tied to flanking or having Advantage from other sources, all the information about them is contained in their description.

Note: It is possible you confused Assassinate for Sneak Attack here, as that can be used every turn, if you have Advantage (eg. due to flanking) or satisfy other conditions. These two are completely separate features, and do not "fuse together" or depend on each other (like what we see with barbarian Rage and other class features). The triggers are evaluated separately, and you can trigger neither, one or both of them in different situations.

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  • \$\begingroup\$ I'd like to clarify "The second part of the feature requires the target to be surprised to grant the automatic crit, and thus will also only work in the first round." This is not entirely true if the assassin / rogue has hidden themself and not engaged in combat in the first round. As a rogue, I frequently hide away from the party so as not to be engaged in combat. I can thus perform a sneak attack when I'm prepared to engage. \$\endgroup\$ – Acts7Seven Jul 8 at 15:37
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    \$\begingroup\$ @Acts7Seven If your DM allows you to use Assassinate under those conditions, you are not playing by RAW. Once combat has started, every creature is assumed to be wary and no surprise is possible. \$\endgroup\$ – Szega Jul 8 at 16:35
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    \$\begingroup\$ @Acts7Seven: As Szega said, surprise can only ever apply to the first round of a combat; if a creature notices any threat at the start of combat, it is not surprised. \$\endgroup\$ – V2Blast Jul 8 at 21:32

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