When should initiative be rolled during a surprise attack?

This question does a good job explaining how surprise attacks work for the most part, but I’m not sure how such an attack would actually play out, here is what happened in my last game:

There was a group of enemy creatures, and the heroes were successfully avoiding notice nearby (I guess they were effectively hiding), watching the creatures and planning what to do while unnoticed.

After agreeing upon a plan, one of the PCs made a ranged attack against an enemy. This catched the enemy flat-footed against the attack, but the PC became observed by everyone after resolving it.

I decided to roll initiative and start the encounter at this point since it made the most sense at the time, but after reading the rules I’m not sure if this played out correctly.

Should initiative have been rolled just before the attack? This seems unfair to the heroes, since according to Avoid Notice it would force another Stealth check to see if the enemies notice them, but the heroes have not done anything yet to break their hiding. And then, if they succeed on the check, what is the point of the enemy turns?, since the heroes are still unnoticed, the enemies would do nothing until the heroes act.

This leads me to believe that the encounter should have started at the moment the heroes spotted the enemy: initiative is rolled according to Avoid Notice and if the heroes succeed on the Stealth check against the Perception DC of the enemies, they remain unnoticed. And all the watching and planning would have ocurred in Encounter Mode (a very long and pointless encounter for the most part).

If this is the correct approach, the heroes could decide to coordinate and attack all at the same time, by delaying to set their turns one after the other, and readying an attack just before the start of the turn of the first hero, so everyone would use their readied attack and then have their full turn before any enemy gets to act. Is this right?

Does Battle Cry happen before or after Initiative is rolled?

The Feat Battle Cry reads

When you roll initiative, you can yell a mighty battle cry and Demoralize an observed foe as a free action. If you’re legendary in Intimidation, you can use a reaction to Demoralize your foe when you critically succeed at an attack roll.

There are similar abilities, such as Hobgoblin Generals’ General’s Cry.

Do effects like this occur before or after initiative is rolled; specifically, does this (potentially) affect the target’s Initiative roll?

When is the Saving Throw rolled for an Infernal Wound?

This came up in a game I was running yesterday.

Two devils (Bearded and Horned) in 5e have weapons that deliver "infernal wounds", which are basically bleed effects. The creatures can be found in the Monster Manual, pgs. 70 and 74, respectively, or here and here.

For convenience, here’s the full text of the ability (Bearded Devil version, bold emphasis mine):

If the target is a creature other than an undead or a construct, it must succeed on a DC 12 Constitution saving throw or lose 5 (1d10) hit points at the start of each of its turns due to an infernal wound. Each time the devil hits the wounded target with this attack, the damage dealt by the wound increases by 5 (1d10). Any creature can take an action to stanch the wound with a successful DC 12 Wisdom (Medicine) check. The wound also closes if the target receives magical healing.

The Horned Devil version coincides word for word with this one, except that the wound damage is 10 (3d6) instead of 5 (1d10) and the Saving Throw DC is 17.

That said, me and my players disagreed over what was the correct interpretation of this rule, namely as to when the save should happen. There are two possible interpretations and both seem grammatically correct:

  1. If the attack hits, the target is wounded, no save rolled. At the start of each of its following turns, the target rolls a Con Save, taking damage only on failures.
  2. If the attack hits, the target rolls a Con Save. On a failure, it is wounded and will take damage on the start of each of its following turns, no save rolled.

Is there any official ruling on what is the correct interpretation?

Does Hexblade’s Curse extra damage affect every die rolled? [duplicate]

The relevant part of Hexblade’s Curse states (XGtE p.55):

Starting at 1st level, you gain the ability to place a baleful curse on someone. As a bonus action, choose one creature you can see within 30 feet of you. The target is cursed for 1 minute. The curse ends early if the target dies, you die, or you are incapacitated. Until the curse ends, you gain the following benefits:

  • You gain a bonus to damage rolls against the cursed target. The bonus equals your proficiency bonus.
  • […]

Typically when features add extra damage they clarify that the extra damage only applies to one damage roll, or the added damage just applies to the damage as a whole, like the various cleric subclasses’ Potent Spellcasting:

Starting at 8th level, you add your wisdom modifier to the damage you deal with any cleric cantrip.

Or the Evocation Wizard’s Empowered Evocation (PHB p.117):

…you can add your Intelligence modifier to one damage roll of any wizard evocation spell you cast.

Does this mean the wording of the Hexblade’s Curse would apply to all of the dice rolled for the attack? If when the warlock gains Pact of the Blade at 3rd level, could they pick a great sword as there pact weapon, which deals 2d6 damage, and add their proficiency bonus twice to the damage?

Peace Cleric’s Emboldening Bond: can the 1d4 be rolled more than once per turn, if it’s only used once?

The Peace Cleric’s Emboldening Bond feature can temporary bond creatures together. The effect is as follow

While any bonded creature is within 30 feet of another, the creature can roll a d4 and add the number rolled to an attack roll, an ability check, or a saving throw it makes. Each creature can add the d4 no more than once per turn.

The text specifies that the 1d4 can be added once per turn.

However, can it be rolled more than once?

For example, suppose I have extra attack, miss, and roll 1 on the 1d4. Could I choose not to add the result of the 1d4 for the first attack, and instead roll it again and add it to the second attack?

Does the Gloom Stalker ranger’s Dread Ambusher feature apply only when the party actually engages in combat, or when initiative is rolled?

The Gloom Stalker ranger’s Dread Ambusher feature says, in part (XGtE, p. 42; emphasis mine):

At the start of your first turn of each combat, your walking speed increases by 10 feet, which lasts until the end of that turn. If you take the Attack action on that turn, you can make one additional weapon attack as part of that action. If that attack hits, the target takes an extra 1d8 damage of the weapon’s damage type

If the DM calls for initiative to be rolled earlier than the party could reasonably engage in "combat" (such as a combat happening at the gates of a city far away, or off in the distance), can the ranger still benefit from Dread Ambusher once actual combat starts for the party/ranger?

The class feature itself doesn’t specify that the ranger needs cover, or surprise, and it doesn’t specifically say that the class feature starts on "initiative" but rather on the first turn of combat.

Or is the benefit of Dread Ambusher just gone if the DM decides to call for initiative more than a round before the ranger can engage in combat?

Should the target of Scrying know that they rolled a Saving Throw?

This is mainly a question about meta information, since players may act differently if they know that something happened requiring a saving throw. Especially if they know that a character will be casting scrying.

Would it be acceptable for a Dungeon Master to secretly roll a character’s save against the Scrying spell?

And (if so) do you think a player would feel cheated if their DM did that?

The spell doesn’t specifically address it, and I’m not aware of a rule that would apply here, so I would think that it would be up to DM discretion, but I would like to make sure.

Thanks.

Troika! How is enemy damage from weapons and super weapons rolled?

In the Troika! SDR page 67 are the enemies Troll and Ven. The Troll does damage as Weapon and the Ven as Super Weapon. But there are no generic damage tables for those.

The Zoanthrop for example does damage as a Modest Beast which is listed in the table of Beastly Weapons on page 70.

How is enemy damage for (Super) Weapon calculated?

A player rolled very bad stats, how to make sure they still enjoy the game?


Question

How to make sure that a player that rolled awful stats will still have an awesome time at the table? What possibilities are available for the DM? Would it feel cheap to find stat-boosting items? What can players do to make sure that player is still having fun?

The simple solution of re-rolling the stats is out of the question. The adventure has already begun and it would feel very unsatisfying if the original rolling carried no weight at all.

Background

Starting a new adventure, we all decided to roll stats (highest 3 of 4d6) for our new characters. Most people rolled stats close to what one would get with point-buy, but one player had all stats in the range 8 to 11 and averaged below 10 (which is worse than a commoner).

The players are all quite new to the game and it is the debut for the GM. We all had some laughs on the horrible rolls and everyone is still having fun. The player has not complained yet, but my worry is that it will feel less fun in the long run.

The player picked druid, so they can wild-shape away the physical stats at level 2.

Does Alchemist’s Fire damage get rolled once, or every turn?

Alchemist’s Fire does things quite differently from other items, being an improvised weapon that must always use ranged attacks, and deals its damage on subsequent turns, not when thrown. And Jeremy Crawford has tweeted a number of clarifications about how the damage works. But there’s one thing that I haven’t found any answers about, whether official, tweet, or even just accepted common practice. Does the damage get re-rolled every turn, or only the once?

On the one hand, only once would make sense with Crawford’s tweets; Dexterity gets added to the damage it deals, because that damage is the one roll made for the weapon’s damage, and the usual rule applies. Which feels more sensible than adding Dex to every roll, turn after turn.

On the other hand, there’s no rule to explicitly say that it’s rolled only once, and ongoing damage is usually re-rolled every time.

So, is the idea supposed to be that the improvised range weapon deals 1d4+dex damage, and the target takes that same damage every turn, or is it that they take a re-rolled 1d4+dex every turn?

For context: I DM, and a player with a Fast Hands-using Thief just brought this up. The whole Dex-to-ongoing-damage thing had always felt a bit off to both of us. He had an idea that his might be the intended interpretation, and I can’t actually find anything anywhere that actually definitively rules either way.