What's your toughest encounter so far.... Mine was an Ancient dragon ( Vulthuryol ) in Blackreach. That was a seriously tough fight. I was totally unprepared. I was expecting a Frost dragon
( level 32 at the time ) and it instantly one shotted 400 health orc in a single breath. Had to spam resist potions like mad and to activate the racial power. Was worth it though, damn dragon actually dropped 600g along with an enchanted Ebony item.

The Potema quest.

Ouch.

Krosis and his Jack-in-the-box impression. I was level ten or so.

I was so proud of taking down that dragon, when suddenly he pops up and says "Hi, there!"

Then I was just as suddenly dead.

Dunno if this counts but the only time I ever backed off from a 'fight' and decided to come back later was with my vampire character that stays in stage 4 all the time so everyone attack you on sight. I wanted to return a completed quest to the Queen in Solitude but there were just too many guards and other NPC's for me to charm them all in time.

I was still using the single target "calm". Having the AoE "pacify" would definitely make it easier. That throne room was harder than any other encounter I've ever faced.

In my current game, I haven't "unlocked" the Dragons yet. I have purposefully avoided talking to the Jarl of Whiterun. So I was out exploring, just going around and collecting Shouts without the threat of Dragon attack, and I wandered onto Krosis's Word Wall... I was level 5 at this point.

H.P. Lovecraft didn't write things as horrifying as what Krosis did to my characters dead body... I can at least say that my death was depressingly quick. I really don't think my Assasssin had time to feel anything as he pretty much one-shotted me.

Krosis. Surprised the crap out of me after I took care of the dragon as well.
Also, Sigdis Gauldurson. That rat bastard must have wiped the floor with me at least 10-20 times before I finally figured him out and proceeded to give him just payback. I almost felt like wailing on his body after his death just fir good measure

By far mine was not an actual boss or mob , but an ability. The disarm shout to be exact. Fighting a boss type and having your weapon shouted off into a huge pile of god-knows-what then scrambling for another weapon in your bags , or like me , I always kept my bags pretty light so had to forage something off the ground really quick before I was roflstomped. Then after narrowly cheating death , having to even in the first place KNOW that's what happened , then having to search all over the room filled with garbage and dead things with poor lighting..... I'll take krosis any day.

I had this happen to me once. I used the "smack Ralof in the back with a dagger" trick to beef my Sneak and One-handed skills during the escape from Helgen, then when I went through Bleak Falls Barrow, the Drauger at the end just happened to be a Death Lord...

He Fus Ro Dah'd my only 5 weapons into another Hold, and I was left fighting him with my fists and quite a bit of foul language. Needless to say, he used my bones as coffin liner.

I restarted a new character shortly after that, and made sure not to repeat that particular mistake.

I got stuck fighting this ghost/wizard dude after emptying three vials into a bowl and sitting on a throne (the good ghost told me to do this). The nasty axe I've been whooping everyone with all game doesn't work against this guy - so I keep dying.

Any advice folks have is more than welcome.

the worst pounding that seemed to go on forever was in Labyrinthium. 2 deathlords.

it took forever and almost all of my health potions to survive the first deathlord.

when the second one showed up.... it took about 20 reloads to beat number 2.

My first character, level 6 (or something) at the time, wondered off into the mountains. Following a snowy path in a snow-storm. I was completely lost, but this desolated path had to lead me somewhere!
Eventually a dragon showed up. My second dragon, and I wasn't prepared at all. I was going to die if I couldn't hide somewhere.
Luckily I found some kind of hole in the ground where I could hide. Eventually the dragon flew off further down the path into the valley.
I emerged from my hole to discover I had reached a large open place between the mountains. In the middle was a large structure, and beneath that structure I saw the dragon fighting a draught (later to be discovered a draughr deadlord).
I wondered closer and suddenly I was surrounded by skeletons. I killed a few skeletons and backed off because the dragon flew away and the deadlord was now coming for me. Behind me were more skeletons, which I killed too.

Now I had to face the deathlord, so I turned around and prepared for a fight. But what was that in the sky? The dragon came back to fight the deadlord! I was saved! The dragon killed the deadlord (while I fired arrows at whatever I could hit).
So now all I had to do is kill a more-than-half-dead dragon. I chucked a resist potion and took cover behind a stone arc. The dragon landed and I charged it with my sword and shield. Succes! The dragon was dead.
So their I was, in the middle of a valley, surrounded by a few dead skeletons, a dead dragon and a dead deadlord. I looted everything I could find and headed further into the valley, because behind the structure the deadlord emerged from, was a set of stairs leading to another structure.

The building on top of the stairs appeared empty, so I headed out on the other side. Behind me I head a coffin cracking. I turn around and I'm standing 3 feet away from another deadlord, screaming a disarm shout at me.
I start running around like a child. Weapon less, almost potion less (spend most of the potions healing while taking cover from the dragon) and no dragon around to save me.
Somehow I manged to jump on to some rocks, out of reach of the new deadlord. I was lucky. He had no bow. It took me half an hour, and a lot of jumping, but I manged to kill the deadlord using my bow.
Or so I thought. It turned out that when almost dead, the deadlord sat down on one knee to restore health. In this position he healed more than I could damage with my bow.
I would have to use my sword. My sword that was shouted out of my hand 30 minutes ago. The second time I got the deadlord into a kneeling position I jumped of my safe spot, and ran to the place my sword should be.
By some miracle I was able to grab my sword and get back to my safe spot before the deadlord returned.
I fired more arrows at it, until it got into the kneeling position again. Now I rushed in with my sword and killed it.
So I claimed my price: The deadlord's ebony sword.

And that is my story about Arcwind Point.

I know what your talking about, i'm lvl 61 so i pwned him, but I'm melee all the way(mostly) and i dual weilded and did the power attack for it. Took like 2 times.

My First fight against Morokei. He's a badass... and rightly so, no complaints. was a good challenge.

Madanach in Cidhna Mine.

I'm 2-handed weapons man, so a shiv or a pickaxe are of little use to me. Nor is magic. Madanach always kills me while I'm slowly chpping away at him with these puny one-handed weapons. That or his friends rush just as I'm about to win.

Any tips on how I can beat him?

My level 10 mage finally killed the Falmer Gloomlurker in the Dwemer Mzulft, but he killed me many, many times before that happened.

Getting the first fragment of the Wuuthrad.

I think I was around level 20 or so, but I play with the PISE mod on master.

I think it was at least 20 draugr deathlords and Farkas was useless as usual.

my preferred weapon of choice

Morokei probably. I was leveling 2-handed (with no perks) and after 2 tries I had to switch to 1-Handed (fully perked for swords).

THIS ^^^^. And add in the fact I didn't know it was Krosis. I was taking a shortcut over the mountains and "Oh look, Lydia, a dragon and he's sleeping perched on top of a rock, and it looks like a word wall. You stay here and I'll sneak behind him, lay the smack down and we're done. Okay?" Wrong. Dragon wakes up. Out pops Krosis and he starts fireballing. And a cave bear joins the fray. I was level 14. I went through ALL of my heal potions. First time I shouted "Run Away!!!!" and Krosis chased me. Lydia stayed and died. Reload. So I had to stay and fight.

Mine was fighting Vokun. I stumbled into the dungeon as a level 13 mage . Best spell: Firebolt (or ball the little apprentice one).

Basically i was fine until half-way through I start facing Deathlords and what not. Luckily there was a NPC with me, she was looking for a book or something.

I had no idea what a dragon priest was until then, so needless to say i ran around the whole time trying to hide behind pillars and shoot my pathetic spell when I had a chance. (My NPC was on one knee 95% of the time).

I got lighting bolted to death at least 10-15 times, then I won a dramatic 40 minute hide and seek game. Needless to say it was the scariest dungeon I have played thus far.

Now my thunderbolt makes dragon priests hide from me

archery draugr death deathlord , one hit from their ebony bow and you are one dead dragonborn,

Alduin... D: I was completely unprepared for it with only 1 health potion and a couple magicka potions. I had no idea that he was going to come right then and there and I felt pretty dumb...

Alduin... D: I was completely unprepared for it with only 1 health potion and a couple magicka potions. I had no idea that he was going to come right then and there and I felt pretty dumb...

My first encounter with the Forsworn as a Sword & Board Nord Warrior. It was the MQ where you are looking for Sky Haven, and the mage-leader kept getting lucky with her damnable spells (I know why Nords, being a warrior race, dislike magic). So I Shouted her off a cliff, and went on to kill the Hagraven. But it turns out the fall didn't kill the Forsworn, because she walked right past the Blades and fried my ass only seconds after I killed the bird-lady. So I reloaded, Shouted her off the cliff again, and double checked to make sure she was dead. She wasn't, but Esbern hadn't caught up to me and Delphine yet, so he Firebolted her face, and I laughed as her lifeless corpse floated down the river. Sweet, sweet victory. Only took 3 tries, and fighting the same Blood Dragon twice. (the second time, some Justicars happened to be in the area, so I sat back and let them get roasted before finishing off the beasty and chowing on it's soul.

Did he stick twisted chemicals into your body in a attempt to Re-animate you?