Hey all. I just created my second character, a Khajit that I'm playing as a thief-sneaking type class. Here are the skills I am working at:

- Sneak (obviously)
- Pickpocket
- Lockpicking
- 1-handed (for dual wielding + dagger(s))
- Light Armor
- Archery

Here are the pros to this:
- Sneak-attacks with a dagger is just flippin' awesome with the animation slitting the throats. 30x critical sneak damage is insane.
- 3x sneak dmg from bow (plus the zoom!) is rewarding
- Fast movement speed and more stamina for running longer distances
- Pickpocketing jacks up your level QUICK!!!
- Makes being the a part of the thieves guild and dark brotherhood very exciting

The cons:
- One-on-one combat against almost anything (except from weak bandits and animals) is very challenging, even on lower difficulties (obviously due to the light armor and no block with dual wielding). I need my personal hired goon to protect me... jeez!
- Not as much armor, but I knew that from the beginning as a compromise.

Basically, a fun build to enjoy playing with a stealth-like motive. I learned that I got about 1/4 (exaggeration) of my levels (now level 22 atm) by pick-pocketing (Save, pick a few from the pockets, save again. If a fail, reload). Just thought I'd share this with you all!

Any thoughts on your stealth-like build character or related skills?

I never seem to be able to sneak behind anyone at all. At best I was able to sneak up on someone sleeping and stab him with my dagger, he woke up and a battle ensued. My sneaking is about 40+ and I am only wearing light armor with as many perks as I could place in sneaking. Am I doing something wrong?

I absolutely LOVE my khajit assassin. I focus on sneak, archery, one hand, illusion, and alchemy. I can stealth kill most enemies but the risk of being caught and having to fight face to face makes it much more fun to roleplay and sneak carefully.

Here is a fun tip/trick: firing arrows away from you enemy can make them go investigate, allowing you to get behind their position if there are somewhere where sneaking up on them proves to be a challenge.

I hear ya on that... what race are ya? My technique is... save before I ensue on an assassination. Just keep working on your sneaking and level it up even more... Join the dark brotherhood and get the awesome light armor that boosts your sneak/archery/attack. That also helps. Plus watch for the enemy pathing, like where do they walk, learn their pattern and wait for them to turn around. Strike.

Try taking your boots off and make sure you don't have a spell in hand when your hands are out for battle.

Once you get all of the archery perks, it's all you ever need.

Thanks, I'm going to try these suggestion.

Check you're 'walking' when you get close at those levels. Shift, I think is the key (not at my pc)

Sneak is a bit of a crapshoot < 50 skill and not at night

Usually I kill them with my bow before we can go into a one-on-one fight or during quests where I know there will be multiple enemies I have a companion who can just run in and take out any close encounters.

Sneaking + Illusion + Archery

Probably the most overpowered combination in the entire game. No one should hit you.... ever. I find that to be very boring imo.

Great way to level your Sneak skill is to find a dungeon full of Draugr and sneak up on 'em while they're sleeping.
Each kill will give you a big boost to the sneak skill leveling it up pretty fast, and they're all sleeping, so they're easy to sneak up on.

That is interesting... I am going to start working on Illusion and add that to my list.