I was DMing my very first (very short) campaign. After a difficult boss fight the party are returning to town. For some god-forsaken reason, the rogue had stolen a bunch of bones from the boss' lair, including the skull of a child. As they approach the outer walls of the town they're stopped by guards, who are rather suspicious of the party (who are largely non-human) and especially of the two Tieflings within.

The rogue quickly realized that the guards were not going to take finding a bunch of remains on the party very well. So he attempted to hide them. Except one. The child's skull. That, he instead decides to plant on the Tiefling paladin. The guards find it. Naturally they're outraged, but the paladin decides to attempt to persuade them that it's all innocent and that nothing is wrong. Natural 1. My heart dropped through my feet, and needless to say, the session did not remain on track.#DDBStyle

I remember hiding from a passing enemy in the bushes surrounding the road. With a crit fail he just looked at me and asked me what was I doing 🤦🏻‍♂️  #DDBStyle

Barely survived an attack on the camp at night and slaying mini-BBEG when the party came across two giant frogs. Imminent TPK as each member went down and I stood alone -- blind and wearing a dire frog on my head -- when my attack finally landed and we survived. #DDBStyle

Most recently I Dm'ed for my group, who was up against a bunch of yakfolk, some good rolls on my end and some bad rolls on theirs got them stripped naked, and put in a cage, ready to be enslaved it was a thrilling escape too. With some of the party possessed by the yakfolk... #DDBStyle

#DDBStyle Introduce a new player to D&D with not tabletop experience they just thought it sounded "cool", in 15 minutes, rolls a nat 1 fall through a gap in the floor and ends up next to a treasure chest, fails investigation roll gets eaten by a mimic, to my surprise comes back next week with a new character and a smile on their face! They still continue to play with us 3 years later and is always the most upbeat player at the table! 

#DDBStyle A couple of heart pounding moments spine to mind, one where my dwarf cleric got knocked unconscious by a group spined devil and the last one used my as a human shield when backing out of the cave. While our ranger tried to shoot it and our wizard was out of spells slots. Failed my first death save and our rogue killed it with vicious mockery one turn before it would’ve attacked me. 
Another is when our wizard got engulfed by an gelatinous cube, low on hp started to suffocate while our ranger held open a gate that was our only escape. Weapons and AC reduced from fighting several black oozes on our way through the dungeon. Our rogue managed to pull him out of the cube but got reduced to single digit HP. Had us running for our lives while this thing squeezed through all the gaps in the gates behind us. 
Then there’s the classic rolling two 1s with advantage or two 20s with disadvantage, rare but they never fail to light up the table when they happen. 
#DDBStyle

Rolled a Nat 2 stealth check while trying to steal an enemy's weapons from beside their bed in the middle of the night. Somehow managed to roll a Nat 20 to convince them we were sleep walking.

#DDBStyle

SPOILER (Dragon of Icespire Peak)

Once upon a time, a company use to enter Gnomengarde and as the reach the first room without care, Faktoré (NPC) got to critical hit (20) against a player miss (1) getting her down right away first room of the first quest. What a start. Same thing couple of room later against a Mimic when all of a sudden a sneaky rogue not paying attention, got to be grapple and eaten by it. They finally survive and got the quest right but ever since then they remembered danger can be in anywhere and their is no room for carelessness.

#DDBStyle

Just played for the first time ever - as a DM - trying to keep the nest of meenlocks hidden from the party and every single stealth roll was so intense!!!! #DDBStyle !!!!!

I really love the Icewind Dale, Rime of the Frostmaiden dice. My characters usually have an ice or cold theme, ability, or item. I just love the way they sparkle on the web page, but the in-person ones are so much better (Which is hard to believe)! The in-person dice comes with a map of Icewind Dale, and some oversized info cards on Icewind Dale.

But that is just how the dice look! here is the terrifying time:

The party's HP was low, the fate of millions rested in my D20, I had to score a 15 or higher. If I failed, there would be no more dice rolling. As I rolled the dice, which felt like it was in slow-mo, thousands of cultists swarmed around us, cultists and party members falling all round, dramatic music seemed to play in my head, when suddenly, the dice stopped rolling. A 20. WE WERE SAVED! That might have been the scariest time of my Dragonborn's life. 

#DDBStyle

The most harrowing dice rolling I have ever been a part of, it's game 1, our very first session and all 4 players are level 1. We got into a fight with a mammoth and it went BAD. Everyone is in death saves, the mammoth has collapsed in a corner because we hurt it so bad but not enough to kill it. Our GM looks sadly at us and declares that "This is a TPK" because even if we made our saves there was no way we wouldn't succumb to the elements and die without medical attention. HOWEVER! I speak up, as the Druid of the group I had cast good berry right before this all went down and ensured that each party member had a berry on them just in case of an emergency. This game we clearly stated that if someone was in Death Saving throws and you rolled a Nat 20 it would result in them waking up with 1 HP, on the flip side rolling a Nat 1 would result in 2 failed death saves. The GM agrees to let us continue rolling out our saves one at a time in order of initiative. Our fighter passes her saves, but no Nat 20. The barbarian passes her saves, but no Nat 20. The Druid passes her saves but no Nat 20. The Ranger..... Nat 20 on her VERY LAST ROLL. We all scream in joy, absolutely freak out, the party isn't dead!! There's still a chance we can all keep playing! And continue we have, we're level 4 now and going strong. #DDBStyle 

In the final battle with Count Strahd von Zarovich things were looking pretty rough.  With the party badly wounded and Strahd coming in for the kill - I utilized the nuclear option on my wizards "staff of power" which I had found earlier in the castle. Broke the staff over my knee causing massive amounts of damage. I then had to roll to see if I died or was teleported to another plane of existence.  odd number is death – even allows my character to continue living. 50-50 chance. I rolled the dice.  Unable to look I had another player tell me the results. A 2! I'm saved! Intense stuff. #ddb-style  

I once played with a group as a "guest." I was only going to play the one time so I had to make it count. My character was a werebear prone to berserk and triggered easily.

The group was in a small stone fort trying to corner their particular bad guy. My character enters the fort and immediately gets into a fight with the bandits that the others painstakingly snuck past. Cleaving my way up to the second story I found the group surrounding the leader. The mage set a wall of flames to trap him.

I attempt to do a superman leap to tackle the bandit leader whose back is to the wall. The DM tells me I may only succeed if I roll a natural 20. I blow on the dice for good luck. Every player holds their breath as the die rolls across the table. 20!

I leap through the air and the bandit leader and I go through the wall and plummet to the ground. I stand badly injured over the dead bandit.

Then we all went fishing.

#DDBStyle

My 2e rogue was trying to steal an artifact level tome from the royal library of Nibenay (Dark Sun setting) when the Sorcerer King sauntered in. I had a 98% chance to succeed on my stealth roll, and I managed to roll a 1. A twenty-minute-long cat and mouse chase through the library ensued that involved a dozen more stealth checks. I passed every one all the way up to the doorway, and then I rolled another 1. He vaporized me halfway out the door. #DDBStyle

I was rolling poorly all night and my die kept missing the dice tower as I threw it in. Then it came time to roll an acrobatics check and a nat20 perfectly balanced on the edge of the tower. Seems only fitting! #DDBStyle

There was that time when I (the DM) killed off my friend's barbarian with a Red Dragon who rolled two nat 20s in a row, swallowing him whole. Or the time when I killed my GF's ranger with Stirges when she rolled a nat 1 and got lost. #DDBStyle

Only every time I'm on 2 death saves... #DDBStyle

I had just started my players on the Curse of Strahd play through.  The first encounter was a Dire wolf accompanied by two standard wolves. 

My level 1 rogue kills a wolf straight away,  so I didn't worry. That didn't last long.  The standard wolf attacked next and killed the rogue.  The Dire wolf attacked the barbarian,  and critted on the first strike.  The damage rolls were low,  but took half the hp. The barbarian attacked next and targeted the Dire wolf,  hurting it,  but not enough.  The third player is a storm sorcerer, and he aimed a thunder wave at the Dire wolf,  kicking him away from the barbarian to prevent pack tactics.  Rogue fails first death saving throw.  The wolf attacks the barbarian,  but misses.  The Dire wolf moves to attack the barbarian and misses.  The barbarian rages and hits the Dire wolf, but it continued to hang in.  The sorcerer uses lightning lure on the wolf but doesn't kill him.  The rogue fails second death save.  Both wolves attack the barbarian only hitting for minor damage,  but has the barbarian at 3 hp. He counter attacks the Dire wolf again,  but misses.  My sorcerer heals the rogue,  who then gets one shotted  by the wolf again.  At this point I  was afraid of a TPK. The barbarian crits the Dire wolf dispatching him, finally. The remaining wolf gets hit by a lightning lure, taking him out. And I let out a sigh of relief. 

I felt terrible that the party had almost died on this first encounter and now has no spell slots or heals to enter the death house.  You have to love Barovia.

#DDBStyle

My party was fighting an ice dragon in her lair. Icy terrain=dex roll each turn. Three turns IN A ROW NAT 1! My supposedly “nimble” half elf rogue WIPED OUT FOR THREE TURNS IN A ROW. I was so mad but it was so hilarious at the same time 😂 then finally crit the dragon at the very end! #DDBStyle