8 Rollback to Revision 5
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@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor'swould allow Victor an attack of opportunity as well becauseif she moves out of his reach - he cannot can now take a reaction for the first turn.reactions b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor's attack of opportunity as well because he cannot take a reaction for the first turn. b) cannot use either of her assassin abilities because: i) Victor has had his turn and ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and a) would allow Victor an attack of opportunity if she moves out of his reach - he can now take reactions b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

7 deleted 9 characters in body
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@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor's attack of opportunity as well because he cannot take a reaction fortfor the first turn. b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor's attack of opportunity as well because he cannot take a reaction fort the first turn. b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor's attack of opportunity as well because he cannot take a reaction for the first turn. b) cannot use either of her assassin abilities because: i) Victor has had his turn and ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

6 I want to change a detail of your explanation because RAW is explicitly stated that surprised creatures do not get any reaction until the turn end and Attack of opportunity are reactions..
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@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) would allow Victor ancan avoid Victor's attack of opportunity if she moves out of his reach -as well because he can nowcannot take reactionsa reaction fort the first turn. b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and a) would allow Victor an attack of opportunity if she moves out of his reach - he can now take reactions b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

@Miniman has answered this correctly but there still seems to be some confusion.

What an assassin can do (PHB p.97):

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.

What surprised is (PHB p.189):

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So surprise has a start "the start of the encounter" and the effects of being 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") have a definite end - the end of your first turn.

It is nonsensical to claim that being "surprised" is a situation that can outlast the end of its effects; can being "unconscious" outlast the effects of unconsciousness?

Following the sequence of play on p.189 and using a very simple 2 creature example:

  1. Determine surprise: Alice the Assassin is not surprised; Victor the Victim is surprised.
  2. Establish positions: we will take that as read.
  3. Roll initiative: There are 2 possibilities:
    1. Alice rolls higher then Victor
    2. Victor rolls higher than Alice
  4. Take Turns

    1. If Alice rolled higher then Victor

      • Alice goes first and can: a) move out of Victor's reach secure in the knowledge that Victorwill not get an Attack of Opportunity - this is a reaction and Victor does not get them until after his first turn. b) use her assassin ability to i) attack with advantage because Victor has not taken a turn (this would be true without surprise and ii) get a critical on any hit because of surprise. If Alice has additional attacks and any bonus actions that grant attacks (e.g. Flurry of Blows or Two Weapon fighting) then this will apply to all of them.

      • Victor then takes his turn and "recovers from surprise".

    2. If Victor rolled higher than Alice

      • Victor takes his turn and "recovers from surprise"
      • Alice takes her turn and can avoid attack of opportunity and: a) can avoid Victor's attack of opportunity as well because he cannot take a reaction fort the first turn. b) cannot use either of her assassin abilities because: for i) Victor has had his turn and for ii) he is no longer surprised.
    3. Begin the next round

If Alice won the initiative then this combat is likely over. If Alice lost the initiative the only advantage she got from surprising Victor was not having him act in the first turn.

5 added link to Miniman's answer
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4 Totally rewritten
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    Post Undeleted by Dale M
3 Totally rewritten
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    Post Deleted by Dale M
2 added 127 characters in body
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1
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