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Slithering in the Undergrowth
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The final build listed here is good for your average game. However, if the enemy team has a high amount of physical damage, avoid the abyssal scepter (in favor of a Randuin's); avoid the Athene's in favor of a Morellonomicon. This also means that you will build a Forbidden Idol over the Chalice early. You can grab an earlier Zhonya's hourglass if you are being bursted or focused a lot. Dropping your W directly onto yourself, and using Zhonya's can be a great way to deal with a melee attacker.
You can upgrade your yellow trinket either way, if you see fit. Red trinket can also be an option.
Building a deathcap isn't the best investment because Cassiopeia's AP scalings are far from stellar.
AP blues will improve your clear drastically, and no other type of rune fits well into that spot. If you feel you need it, you could go magic resist, but this will hurt you pretty badly in the beginning.
The health regen yellows are by far the most efficient when jungling. Since you are almost always at less than full health, they are always in effect, and will yield you much more effective health than armor or flat health.
Attack speed reds and quints let you make maximum use of that hunter's machete heal and bonus damage, which is what really gets you through the jungle the first time around.
Masteries are 9/21/0, once again to help you survive. Most of the mastery page is fairly self-explanatory. There are two things to note here. First, you take attack speed and attack damage in the offense tree. The attack speed is, once again, to make good use of that machete. The attack damage is much more efficient in the first clear than the AP, so take it since the missing 22 AP won't really matter towards the end of the game. Second, the Oppression mastery will essentially reduce your damage taken in the jungle by 3% because of the slow on your W. This is absolutely essential.
1. Upgrades increase the slow, which will increase your resilience to counterjungling, as well as make your ganks slightly better.
2. All of Cassiopeia's skills cost an extra 10 mana per upgrade. You can't really afford to use your E a lot in the first place, so you don't want to upgrade that. The damage increase per second per upgrade is roughly the same for Q and for W. However, W is on a 9 second cooldown, while Q is on a 3 second cooldown, making W by far the more mana efficient choice.
You will have to make good use of Cassiopeia's passive to sustain in the jungle. Between every camp, cast your q every few seconds to keep 5 stacks of your passive up. This will cut your mana costs in half, more than making up for the wasted q's you will be dropping in empty jungle.
You will max your E second because it is your main damage source against champions. By the time you are putting your 3rd or 4th point in this skill, you should be moving into the teamfight stage, meaning this damage output is very important. Furthermore, because you use your Q to keep your passive up when jungling, you will want to max this one last to make sure you don't run out of mana.
When you do gank, try to save your slow pool until the laner uses any gap closers they have. Start using Q and E (and autoattacks if you have red buff) as soon as you are in range. Do NOT use your E on someone unless they are either poisoned, about to escape (under tower or into their jungle), or about to die. You don't want to have that ability on cooldown in the middle of a gank.
Be extremely careful when ganking burst mages or other high damage champs (Le Blanc, Veigar, Zed, post-6 Jax, Lee Sin, etc.), as you are somewhat squishy.