Ok, we might have bit off more than we can chew with that title, but let's try it anyway!
Ravenloft: Horrors Within gives us four new backgrounds, two standard Origin Feats, and then several Dark Gifts, which have been redesigned to now function as alternative "Origin Feats with a downside." They're actually not unlike Complications from Draw Steel.
Let's get started:
(Note, I'm going to skip background equipment.)
Haunted One:
Appearing first in Curse of Strahd, Haunted Ones are plagued by a traumatic, horrific event (aka 75% of D&D backstories).
Ability Scores: Con, Wis, Cha
Feat: Survivor (see below) or a Dark Gift of your choice
Skills: Arcana, Survival
Tool Proficiency: Gaming Set of your choice
The old Haunted One was actually really flexible, letting you choose your skills, though it came with zero gold. This is going to naturally suit Clerics, Druids, Warlocks, Bards, and Sorcerers best, as it doesn't boost any weapon-based abilities. Survivor is kind of an alternative to Alert with a little help against fear and charm effects.
Investigator:
You're a relentless seeker of truth. Weirdly seems to overlap with the Inquisitive from Eberron (though that was more specifically a Private Eye type).
Ability Scores: Intelligence, Wisdom, Charisma
Feat: Sharp Eye (see below) or a Dark Gift of your choice.
Skills: Insight, Investigation
Tools: Disguise Kit
Sadly, the ability scores here are not a great spread, as while anyone with any spellcasting will be happy to take one of these, you don't get to then give your secondary bonus to something like Con or Dex. Rarely does a PC rely on two mental stats for their class abilities.
Mist Wanderer:
Here, you might take this as a member of the Vistani, or anyone else who wanders the Domains of Dread.
Ability Scores: Dex, Con, Wis
Feat: Choose a Dark Gift (Mist Walker recommended as the default)
Skills: Survival, Stealth
Tools: One kind of Artisan's Tools
Mist Walker, to spoil later stuff, is not quite as onerous as it was in Van Richten's. The ability spread here works great for any Dex or Wis-based character. Naturally, Monks and Rangers are going to love all three of these abilities.
Spirit Medium:
You have a connection to the spirits of the dead, acting as a conduit for them to interact with the living, for good or ill.
Ability Scores: Con, Int, Wis
Feat: A Dark Gift of your choice (Gathered Whispers recommended as the default)
Skills: Insight, Religion
Tools: One type of gaming set of your choice.
The huge oversight is that this doesn't work well for a College of Spirits Bard, as you can't get Charisma. Again, my biggest issue with 5.5 (other than WotC's bias toward reprinting stuff from 5.0) is that backgrounds are as restrictive as the old Races/Species were. Brings us back to the post-Tasha's 5.0 glory days when we could really pick whatever we wanted! (Make a custom background that uses most of this, I say).
Origin Feats:
I separate out the standard Origin Feats simply because they're listed separately from the Dark Gifts, but make no mistake, a Dark Gift now functions as an Origin Feat.
Sharp Eye:
When you take the Search or Study action (basically any Int or Wis ability check) you can give yourself advantage on the roll. You can do this PB times per long rest, but you only expend the use if you succeed on the roll.
I hadn't actually noticed the bad luck protection element here on my first read of it, so I actually think this is pretty solid. Naturally it's less combat-focused, but I actually think that some of the combat-focused Origin feats aren't really worth it. Great for your party's main scout or researcher.
Survivor:
You get two benefits:
First, if you roll initiative and get a 9 or lower on the d20, you can reroll it (and must use the new roll).
Second, when you fail a save to avoid or end the Charmed or Frightened condition, you can take a reaction to add your PB to the roll, potentially turning it into a success. You can take this reaction once per long rest.
The second part is very limited in use, but could come in clutch. The first part is interesting when comparing it with Alert. Advantage on Initiative means a d20 becomes 13.825 (didn't do the math, just looked it up). This would make the average 12.975 (this I did do the math on) assuming you always roll it if you land a 9 or lower. And that kind of makes sense, advantage might improve a 14 to a 17 or something, while this only boosts your average roll when you roll low.
That means the secondary part is really what distinguishes this from Alert, and I still think Alert wins overall, but to be fair, a Ravenloft campaign is very likely to have a lot of Charm and Fear effects.
Dark Gifts:
Dark Gifts take the place of an Origin Feat, though a character might also earn a Dark Gift in the middle of a campaign for plot reasons. Each gives you a benefit and then a (usually rare) downside.
I would really approach these Dark Gifts more from a RP/Storytelling point of view than for pure power, though it's interesting to know which ones would be particularly useful.
Aberrant Anatomy:
Like the reveal at the Shadow Over Innsmouth, your exposure or hidden lineage related to alien horrors of the Far Realm has warped your anatomy.
You can hold your breath for 1 hour. You also gain proficiency in Perception if you lack it, and also gain Expertise in it. You also get Blindsight out to 15 feet.
If you roll a 1 on a d20 test (I'm just going to say if you get a natural one from here on out) the aberrant influence threatens to overwhelm you. You must make a Con save (DC equal 13 plus your proficiency bonus) or be stunned until the end of your next turn.
Those are some pretty good benefits. Play a class with Con save proficiency, maybe? Actually, a Sorcerer who focuses a lot on spell attacks could really reduce the danger here by using Innate Sorcery for advantage.
Echoing Soul:
Echoes of past lives flit into your consciousness.
You have proficiency in two skills of your choice, and you can choose one skill with which you have proficiency and gain Expertise in it. When you finish a long rest, you can swap which skill has expertise.
You also learn an additional language.
After you roll a nat 1, your memories threaten to overtake your current identity. Make a Con save (DC 13 + PB). On a failure, you're Incapacitated until the end of your next turn, and your speed is halved while incapacitated.
Definitely good for classes that focus a lot on skills. The downside isn't as bad as Aberrant Anatomy, but nearly as much.
Gathered Whispers:
You are haunted by a cacophony of whispers only you can hear.
You learn Message and can cast it without material components. You also automatically have Augury prepared. You can cast it without a spell slot or spell components once per long rest.
When you are hit with an attack roll, you can use a reaction to channel the haunting spirits around you to protect you with a scream, adding your PB to your AC. You can use this PB times per long rest.
If you roll a nat 1, you have to make a Wisdom save (DC 13 + PB) or have the Deafened condition until your next turn. While deafened, you have disadvantage on attack rolls and ability checks.
This is super-good. It's not quite the Shield Spell (it only works on one attack per use and isn't as big of a bonus until level 13) but still quite good, and frankly, the downside isn't too bad, especially if you're a caster who mostly does saving-throw-based spells.
Living Shadow
Your shadow is somewhat autonomous and ever-present, and can act on the world around you.
You learn Mage Hand. Also, PB times per long rest, you can extend the reach of a melee attack by 10 feet.
If you roll a nat 1, you must make a Wisdom save, DC 13+PB. On a failure, you're Incpacitated until the start of your next turn, at which point you must roll on the "Shadow's Will" table, rolling a d8.
1: You don't take an action or bonus action, and you use all your movement to move randomly in one of the four cardinal directions.
2-6: You don't move or take a bonus action, and you take the Attack action to make one melee attack against a random creature within reach (if there is none, you take no action).
7-8: You have the prone condition and your turn ends.
It's certainly the most fun downside so far, and if you wind up attacking a foe, it might wind up working out for you. The benefit is ok, but the flavor is delightful.
Mist Walker:
You are adept at traversing the Mists, but the Mists seek to drain your life force if you stop anywhere for too long.
When you enter the Mists with the intent of reaching a specific domain, you act as a Mist Talisman keyed to that domain, allowing you to arrive in the chosen region as long as the Darklords have not closed the borders.
When you take damage or fail a saving throw to avoid the Grappled or Restrained condition, you can take a reaction to teleport up to 15 feet to an unoccupied space you can see. You can do this PB times per long rest.
If you finish a long rest, the wordl around you in a 10-mile radius starts to siphon the life from you. When you finish a short rest in that area, you make a Con save (DC 13+PB). On a failure, you don't benefit from the rest.
I actually think this is not too bad: while you might be wary of this on a class that relies a lot on short rests (Fighter, Warlock, Monk) this doesn't affect Long Rests in any way. And while a 10-mile radius will cover a pretty wide swath of many domains, some are far larger, so you might not even have too much trouble as long as your party is on the move.
Second Skin:
There is a second form you take on - whether a ghastly beast, terrifying avenger, or walking nightmare. (Wow, this is actually very good for a Barbarian concept I had).
You always have Alter Self prepared, and can cast it once per long rest for free. When you use your free use of the spell, it doesn't require concentration.
Certain circumstances can involuntarily trigger the change - you roll on the Change Catalys table to determine what it is. After seeing your catalyst, you make a Charisma save (DC 13+PB, you know the drill) and on a failure, you instantly cast Alter Self without a spell slot. If you've already expended that free use of it, you are instead Stunned until the start of your next turn.
Change Catalysts:
1: Seeing a particular phase of the moon.
2: Smelling the scent of a certain type of flower
3: Hearing temple bells ringing
4: Hearing a particular melody (shades of Father Gascoigne's music box?)
5: Touching pure silver with your bare skin
6: Seeing someone who resembles a specific individual
Another route here to do the Werewolf thing, though it's pretty loose in flavor. I think DMs will need to be cautious about over-exposing them to their catalysts, though it might be exciting to have the party need to go somewhere where the catalyst is present - a field of roses somewhere in Sithicus, for example.
Symbiotic Being:
A second being lives in your body, offering knowledge and assistance while pursuing its own agenda.
The symbiote cannot be targeted and if you or the symbiote dies, the other does as well. You gain proficiency in either Arcana, Deception, History, Intimidation, Insight, Investigation, Nature, Religion, Perception, or Persuasion. You also learn one additional language.
When you fail a saving throw, you can expend a hit die, and roll it and then add it to the saving throw, potentially making it succeed. You can do this PB times per long rest.
When you roll a nat 1, the Symbiote attempts to take control of your body. Make a Charisma saving throw (DC 13+PB). On a failure, you're charmed for 1d12 hours, and must obey the Symbiote's commands and further its goals, as determined by the DM. When you take damage, you can repeat the save and end the condition on a success.
At the DM's discretion, if you act against the symbiote's agenda, you might have to make the saving throw anyway.
That last bit is a big lever to give to DMs. As a DM, try to make the agenda not necessarily clash with the party's goals, at least not all the time. An affable (even if sinister) symbiote I think makes for a better story.
Touch of Death:
You learn Chill Touch, can cast it without spell components, and the necrotic damage it deals ignores resistance.
You also have disadvantage on Death saving throws.
I hate this one. It's almost strictly worse than Magic Initiate: Wizard. It's a dangerous downside with very little upside. And worst of all, it's boring.
Watchers:
Something is always watching you, taking the form of eerie creatures and vermin.
You always have Beast Sense and Speak with Animals prepared, and can cast each for free once per Long Rest.
When you take the Search action (aka most Wisdom checks, except I think Animal Handling, which is Influence) you can add a d4 to the ability roll.
You have disadvantage on saving throws against the Scrying spell, and when you roll a nat 1, you must make a Wisdom saving throw as paranoia overwhelms you (DC 13+PB). On a failure, you have disadvantage on all d20 tests for a minute, but you can repeat this save on the end of each of your turns, ending it early on a success.
I think this is a real flavor win. And it's fun on a high-wisdom character. Paranoia is such a potent theme in horror, and I think leaning into that (and also letting the DM narrate weird watchers like the Staring Cats of Ulun-Dar is super fun).
Overall Thoughts:
I like the Dark Gifts, and I think making them alternate Origin Feats gives them a mechnical identity that really makes it easy to slot them into your character. I'd highly recommend that if you run a Ravenloft campaign, you should encourage people to take these at character creation. Most are actually pretty potent (too bad Touch of Death sucks).
It's a bummer that none of the four backgrounds work with Strength. Again, I think that backgrounds (even with their fantastic art) are the biggest weakness in 5.5, and one that you're always basically going to want to customize out of, which makes it less exciting to get new ones. If it were just starting equipment, skills, and origin feats, I think it'd be far better.
I think our next big look will be at monsters - probably a broader overview rather than a deep dive on every single one.
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