Of all the different skills in Skyrim, Pickpocket may be the most complicated and hardest to understand, as its various interactions with NPC characters can result in some overly complicated calculations that the player may not be aware of how to take advantage of, and that's if they're even aware they exist to begin with. That being said, it is definitely a skill worth investing in for the long run.
Although Septims aren't exactly hard to come across in Skyrim, the Pickpocket skill not only allows the player to gain significantly more money but also saves a huge amount of coin in other scenarios, which can help immensely when trying to obtain the Golden Touch achievement or trophy.
10 How Experience Is Gained
Like all skills in Skryim, experience is gained by using a particular skill repetitively. In the Pickpocket skill's case, it is gained by successfully pickpocketing NPCs, though there are ways to increase the amount of experience gained each time, as, not unlike magic skills, the experience gained increases based on the difficulty of the attempt. For the most part, you gain more experience for Pickpocketing items of higher values, though this also increases the difficulty of the attempt and can result in failure more frequently. The easiest way around this is to simply quicksave before attempting to pickpocket and reloading the save if it fails.
9 The Zero Percentage Chance
Although the percentage chance shown is a half-decent indicator of the difficulty of the pickpocket attempt, it doesn't always reflect the reality of the difficulty. A percentage chance of 50% is still a pretty good chance, especially if you are quicksaving before the attempt, as you are still likely to succeed in the first few tries. Sometimes, however, there will be a 0% chance shown, though this doesn't mean that there is no chance of succeeding — it simply means that there is less than 1% chance and the game does not display fractions of whole numbers.
8 The Hard Septim Limit
Although the Pickpocket skill can allow you to take large amounts of money, there is a hard limit set on how much can be taken at a time. No matter what level Pickpocket the Dragonborn is, they can never take more than 999 Septims at a time, so if a character you are attempting to pickpocket has more than this, it will fail every time.
There isn't a way of taking a set amount of Septims repeatedly to circumvent this limit. But there is a handful of ways you can get around it — either through items, spells, or shouts that often go a long way in making leveling up Pickpocket go much faster.
7 Your Target Isn't The Only Factor In Sneaking
Even if your Sneak skill is at level 100 and most NPCs won't spot you if you're crouching right in front of them in broad daylight, the pickpocket attempt will always fail if you are being seen by someone else. At lower levels, you may need to get creative in positioning yourself to avoid being seen by either the target or anyone else. Admittedly, having a high level of Sneak helps quite a bit, but timing will almost invariably be a factor in crowded places.
6 There Is Always A Chance To Fail
Unlike the Lockpick skill, which can stop lockpicks from breaking once the Last Dragonborn takes the level 100 perk, Pickpocket has no such perk that ensures all chances will be 100% successful. Even if the Last Dragonborn is level 100 in both Sneak and Pickpocket, there is always a chance that the target will catch them in the act as the chance of success is capped at 90%. This can't be increased through the use of potions or enchantments, either — that can actually be a bad idea, which we'll touch on later.
5 Circumventing The Limits With Poison
Although there are several hard limits on how much you can steal and the chance of success, there are ways around these limits to ensure a 100% success rate. The Poisoned perk which can be obtained at level 40 allows you to poison an NPC by reverse pickpocketing a poison into their inventory. While this is basically useless in combat scenarios, it is very useful with Paralysis poisons, as a paralyzed NPC can be pickpocketed from with no limit and, if done successfully, they won't turn hostile to the player.
4 Circumventing The Limits With Magic
Another way to circumvent the hard limitations also involves paralysis, but also needs some higher levels in Illusion and Alteration to pull off successfully. If you have both the Quiet Casting perk from the Illusion skill tree and enough skill in Alteration to use the Paralysis spell, you can use this instead to paralyze the target without being seen.
This can be quite hard to pull off early in the game, as Alteration is notoriously hard to level up without spamming Waterbreathing in a river or using Telekinesis over and over again, but it has an advantage over the Paralysis poison route in that you don't have to keep crafting poisons to pull it off.
3 Potential For Negative Bonuses
At this point, it's fairly well known by veteran Skyrim players that the Alchemy skill is entirely broken and allows for some ridiculous stat buffs when combined with other skills, most notably Enchanting. With both Fortify Pickpocket enchantments and potions, it is possible for the positive effects to turn into negative ones if the value of the item is too low, similarly to how too high a Fortify potion created using the Restoration enchantment loop can result in negative effects instead. For the most part, Fortify Pickpocket enchantments are only worth using for the first few levels, and any attempts to increase the likelihood of success are better done with Paralysis instead.
2 Free Experience Training
By far the best way to level up the Pickpocket skill early, as well as any other skill in the game, is to pickpocket a skill trainer. NPCs such as Faedal in Riverwood can be paid to increase certain skills by one level, then you can simply steal the money back for a free level in the skill of your choice while also increasing the Pickpocket skill. The best use of this is to increase the level of hard-to-improve skills, such as the Light or Heavy armor skills or the Destruction and Alteration magic skills.
1 Items Limited To Pickpocketing
For some reason, there are items in the game that can't be obtained unless you have the Misdirection or Perfect Touch perks in the Pickpocket skill. The most notable of these are the Glass Bow of the Stag Prince, which is oftentimes a glitched item with the trader and he will often equip it rather than sell it like he is supposed to, as well as the Fine Armguards worn by Bryling in Solitude. These armguards are unique among other armor pieces in that while they provide an armor rating, they won't prevent the use of the Mage Armor Alteration perk increasing the effectiveness of Flesh spells.