*The race, in the long run, really doesn't matter because there are no races that give a direct ability to sneak. For the race that has a good ability, use the Khajiit (Night Eye: explained later) or Orc (Berserker Rage: also explained later). Also, an Argonian, Dark elf, and Wood elf all have +5 sneak, but the Khajiit have +10 sneak. Orcs are a good choice because of their racial power. With their racial power, Orcs can deal 600 damage with as little as an iron dagger that's un-upgraded, a few perks in sneak and shrouded gloves.
The racial strengths and powers of the races that will do good as an assassin:
1) The Khajiit: Night Eye. +10 Sneak: You can see in the dark when this is activated for 60 seconds. It has no cool-down.
2) The Orismer (The Orcs): +0 Sneak: Berserker Rage. Deal 2x damage and take half damage.
3) The Argonian: Waterbreathing. Constant water breathing . . . not that helpful, unless you are escaping from guards and there is water nearby.
4) The Dunmer (The Dark Elves): Ancestral Fire. Flame cloak once a day for 60 seconds. (Flame cloak is when you are surrounded by fire and deal 8 points of damage a second to every enemy around you.)
5) The Bosmer (The Wood Elves): Resist poison and disease by 50%. Also has Command animal, which commands any animal, including mammoths.
The Argonian, The Dunmer, and The Bosmer all have +5 sneak.
**SIde Note** Did anyone else notice a pattern with assassins? All the races I posted were either The Beast Races or The Mer (the elves).
*The armor should be light armor. (I will get into wearing heavy armor and sneaking a little later in this article.) I recommend these armor pieces:
Shrouded Hood/Cicero's Hat/Jester's Hat: Gives the wearer 20%, 35% sneak bonus, 30% sneak bonus, respectively. All these are from the Dark Brotherhood.
Dragonscale armor: The BEST armor rating for light armor in the game. You can smith this at 100 smithing, or possibly find this in a dungeon starting at around level 40.
Silver Necklace: Enchant this with sneak, lockpicking or pickpocket bonus (you will be needing these if you decide to skip out on smithing, which I don't recommend for new players to Skyrim or to Master difficulty). Silver is the cheapest jewelry to make.
Silver ring: Enchanted with sneak, lockpicking or pickpocket bonus. My reason is the same as above.
Ancient Shrouded Gloves: 2x one-handed damage, not just backstab like the regular shrouded gloves. Also has a high armor rating (for light armor).
Ancient/Shrouded boots/nightingale boot/any other boots with muffle effect: All the boots have muffle, so pick the best armor rating unless you prefer form over function.
*minor spoiler*You can replace the lockpicking bonus with the Skeleton Key from the Thieves Guild quests.*minor spoiler*
How to use Heavy Armor and sneak effectively:
*You can use heavy armor with a few perks/armor/stone. There is a piece of armor (Second best heavy armor in the game) called Ebony Mail (will explain later) that makes you silent and deals poison damage to everyone around you.
*Use the Steed stone, which is northwest of Solitude. The steed stone grants a bonus of Conditioning (your armor is weightless when you wear it) and it adds +100 carry weight. With that, enchant ALL your armor and apparel with sneak bonuses. You cannot risk to lose any sneaking if you choose to wear heavy armor. Once you reach level 70 Heavy Armor you can get the Conditioning perk, and lose the steed stone for another stone, preferably the Shadow stone which grants invisibility once a day.
1) Do the Dark Brotherhood then the Thieves guild before anything else. If you don't want to do these, that's okay, although it'll help you since the best sneak gear is from those two guilds.
2) Make use of your bow. Use it 'till the enemy is close, stay hidden (use invisibility is needed), then use your dagger.
3) Don't use companions or summoned creatures. (Even if they have a "high" sneak skill, they are almost inevitably found by the enemy.)
4) It is recommended that you don't do the main quest until you have good armor and weapons (glass and above), and a sneak skill of 80 or above. The same is true for your combat skills and your illusion skill. There are hard enemies that spawn when you do the main quest.
5) Be creative! Some lights can be shot down. Torches can be taken and sentries killed. You might want to pick off some enemies with your bow for easier kills with your dagger.
6) Don't feel threatened to play on master difficulty, but don't dip lower than adept. Expert/Master difficulty is what I based this guide on.
Skills and perks recommended for Heavy Armor:
Heavy Armor: Upgrade to the conditioning perk. Get 5/5 juggernaut and matching set.
Archery: ^ see note below.
One-handed: Get armsman 4/5, and all the dual wielding perks.
Sneak: ^ see note below.
Smithing: Get the right side of the tree and Arcane Blacksmith. ^^ see note below.
Illusion: Get up to expert illusion reduction and quiet casting.
Enchanting: Get Enchanter 5/5 and Extra Effect. ^^ see note below.
If you are using light armor, replace light armor for heavy:
Light Armor: ^
^: Get all the perks and fully upgrade the perks that have upgrades on them.
^^: Not needed, but recommended for better sneak attack damage. (Especially not needed if you are an orc and don't mind waiting for 24 hours a lot more than you might be use to.)
*While you get an achievement after all the daedric artifacts are obtained, the artifacts are not as strong (base damage or base armor rating) as the smithable daedric equipment (e.g. daedric dagger, daedric mace ect.) (They do have unique enchants, though.)
Mehrunes Razor: Dagger with a 3% chance to instantly kill an enemy. The enchantmant is quite pointless after level 20, which is the level you earn it. BUT it is half the weight of a daedric dagger and the same base damage. Theoretically, it swings 2x as fast and deals double (base) damage. It cannot be upgraded to or past legendary without potions or encantments because no perk is associated with it even though it requires ebony ingots to upgrade. Requires level 20.
Savior's Hide: With a high enough sneak, you can replace dragonscale with this armor. It gives a 50% poison resist and a 15% magic resist. Requires level 13. It is good light armor for this early on.
Ebony Mail: A good heavy armor that makes you silent and you deal poison damage. Has a base armor rating of 45, just 4 less than daedric armor. So assassins are better with this than they are with daedric armor. Be warned that if you are using a bow, the poison will block your view. But you can learn of enemies that you weren't aware of before.
Weapons to use in the late game:*You should always keep your favorite, light-weight, weapons at your side. There are no unique daggers (besides Mehrunes Razor) that are worth the Skyrim assassin using. The nightingale bow, on the other hand, is a great bow with nice enchantments (Frost, shock, and stamina damage that depends on the level you get it). It is acquired at the end of the Thieves Guild. Besides that, the daedric daggers and bows are the best weapons in the game. Those are what, if you followed the guide exactly, you will be using in the late game.
***Note that this is for the assassin only. I didn't put any perks (enchants are not perks) to any other stealth skill other than sneak itself. You can still steal, although it'll be harder than if you're a thief.***
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