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TangoTangoTango
Stout Shield
Morbid Mask
Smoke of Deceit
Boots of Speed
Blades of Attack
Blades of Attack
Phase Boots
Shadow Blade
Black King Bar
Satanic
Skull Basher
Vanguard
Assault Cuirass
Daedalus
Boots of Travel
Blink Dagger
Desolator
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7 | 12 | 13 | 14 |  |
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2 | 3 | 5 | 9 |  |
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1 | 4 | 8 | 10 |  |
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6 | 11 | 16 |  |
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15 | 17 | 18 |
(You can subscribe to this ingame guide to use this build ingame)
This is a simple guide on how to jungle with 
Ursa, from level 1, up until the time you can beat Roshan by yourself. It doesn't focus on how to play Ursa, and the expansions suggestions here are just some popular choices. The beginning is pretty standard, though, and is suggested by DotA 2 suggestions as well.
Also, this is not a competitive guide, but rather a fun pub jungler. I don't really know if Ursa can be played on jungle on tournament play effectively.
The major requirement to do this is the knowledge about creep camps, as well as respawn time. I've placed a few images to help with the camps selection, but there is this good link that can be used as well: http://www.dota2wiki.com/wiki/Creeps
About respawning, the best way to describe how they work is to say that, every once in a while, creep camps that have noone standing there, will spawn some new creeps.
This happens the first time at 0:30, and then every whole minute (1:00, 2:00, 3:00, ...)
If you manage to lure the creeps out of the camp at the exact time in which camps respawn, the camps will spawn a new wave of creeps, and then the previous batch will walk back to the camp. This is called STACKING CAMPS. (update: since a new patch, creeps from easy camp now will follow you only for 5s)
Since neutral creeps will follow you for 7 seconds out of the camp (this is part of the game mechanics), what we do is leave camp 7s before the spawn, which would be at 0:53, 1:53, 2:53, and so on.
Pros:
+ High Armor
+ High Life
+ High Damage, using Fury Swipes
+ Can do Roshan alone within 7 minutes!
+ Can jungle using medium camps (don't mess with pulls)
Cons:
- Slow attack speed when not using Overpower
- Depends on healings to go jungle (no lifesteal)
I've updated this guide to patch 6.81. Since this patch, Fury Swipes is no longer an Unique Attack Modifier, meaning that Ursa can now hold Morbid Mask without losing its high damage output. This accelerates Roshan to around 7 minutes!
Don't forget, you can use the ingame guide to help you out.
Start with Stout Shield and 3 sets of Tangos (to a total of 12 Tango charges). This will ensure that you can stay in jungle long enough to rush Morbid Mask, which is the item that allows Ursa to kill Roshan by itself.
Ursa is good at jungling because it has Fury Swipes, which allows it to kill creep camps fast enough to be viable. As such, your first skill will be Fury Swipes
Creeps camps spawn for the first time at 00:30 in the game. You should move to a Medium camp, as shown in the image bellow:
.
(Yellow dots are the medium camps, since update 6.79)
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Don't stand over it, or the creeps won't spawn. Enter the camp after 00:30 in the timer.
You can easily kill the creeps and keep on using Tango to recover your health.
After you kill this camp, move to the next medium camp:
.
(As a sidenote, the route suggested on radiant side allows you check rune in the process, and dire is also close to rune)
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Proceed killing the medium camp. By far, the hardest camp is the one with Centaurs. This is because they have enough damage to hurt you even when Stout Shield blocks. Be sure to regen a bit BEFORE facing them.
As you keep on jumping from medium camp to medium camp, you will have enough gold for Morbid Mask. Buy it as soon as you can, which should be around level 4 or 5, depending on the creeps you face.
Roshan can be done as soon as you buy Morbid Mask. I recomend a level 5 Ursa to be sure not to die for too much stuns. Do yourself a favor, to avoid enemy's wards, and buy a Smoke of Deceit. You will need to have full life+mana and Overpower (heal at fountain if needed, it's worthy it).
How to proceed with Rosh:
First, use Overpower before starting the fight. DON'T start the fight before cooldown for Overpower ends cooling. After it ends, start the fight, and RECAST Overpower as soon as the first one finishes. This will grant you a huge bonus damage against Roshan, making your lifesteal very effective, and letting you finish it within 7 minutes in the game. =D
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Test run - Roshan bites the dust with 6min 48s
For here on, it's smooth sailing (or at least here is where the team game begins). Popular extensions are Phase Boots, Blink Dagger and Black King Bar, as well as 
Sange and Yasha or Vanguard or Skull Basher.
Since the 6.81 patch, Satanic is a good item to go for, since Ursa benefits well from extra life with its ultimate.
I recomend you getting at least one item to shorten the distance before anything else, in Shadow Blade or Blink Dagger (even tho Phase Boots help). After that, it's up to you whether you want more DPS or more survivability.
My thanks to everyone for taking your time and reading this guide. Feel free to drop a comment if there's anything wrong, and don't forget to upvote if you like it. =D
My guides:
A brief guide to jungle Ursa until solo Roshan
Rylai Crestfall, the Support Maiden
LoL w00t Viper
Non-pro Winter Wyvern - a different build for after the nerfs
May 07 2014
- Changed a bit the skill build order: Overpower is slightly more important for the early Roshan than Fury Swipes on 5. Roshan gives 3 levels when done, so I antecipated Enrage and Earthshock.
- Added Desolator to popular extensions.
Apr 30 2014
- Updated for patch 6.81: Fury Swipes no longer an Unique Attack Modifier
- Roshan can now be done solely with Morbid Mask
Apr 24 2014
- Still viable. Organized community (ingame) guide a bit.
Feb 4 2014
- Revision - still up-to-date
Nov 10 2013
- Updated for patch 6.79
Aug 20 2013
- Added tip to buy Smoke of Deceit before going Roshan.
- Added a note on how to accelerate the farm by skipping a tango.
Jan 7 2016
- Small fixes
Note: I want to test 
Iron Talon, but until I do, this guide is still viable.
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