Hello and welcome to the 100% Achievements Guide for Tails of Iron 2: Whiskers of Winter.
I hope this guid will help you out.

There are a total of 27 achievements, but since you don't have to play on the hardest difficulty, getting 100% is a pretty easy. I've split the achievements into several sections based on their type.

You can also track down your achievements (and counters) in the game:
Open Menu → Extra → Medals

‼️WARNING‼️ This guide contains some spoilers - main plot spoilers are hidden.
I really recommend playing through the game at least once before diving into this or come back to this guide after finishing the game.

If you spot any mistakes or have suggestions, drop a comment!

In this section, you'll mostly be grinding kills. Just head into the area, take out the mobs, then leave and come back so they respawn.

Defeat 25 BackStabbers
Defeat 25 BackStabbers in combat.


Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

Use this spot on the Outskirts map during the day:

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Defeat 25 Birds
Defeat 25 Birds in combat.

Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

Use this spot on the Outskirts map during the night:

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Defeat 25 Death Marches
Defeat 25 Death Marches in combat.[

Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

Use this spot on the Golden Forest during the day:

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Defeat 25 Frogs
Defeat 25 Frogs in combat.

The main and side quests will cover this, so there is no need to grind them.

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Defeat 25 Mudwyrms
Defeat 25 Mudwyrms in combat.

Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

Use this spot on the Outskirts - top left at night (1 enemy):


OR use birds spot during the day (2 enemies.)

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Defeat 25 Owl Cultists
Defeat 25 Owl Cultists in combat.

Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

No particular spot, they're all over the map (the Golden Forest).

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Defeat 25 Tailspinners
Defeat 25 Tailspinners in combat.

Probably doing the main and side quests won't cover this, so you'll have to grind a bit.

No particular spot, they're all over the map (the Rift).

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Defeat Harat Bluefang
Defeat the Draugr in the Tomb of the Old King.


For this achievement you'll need to defeat Draugr in the locked area shown below:


To unlock the Tomb of the Old King, you'll need to grab 4 runestones:

1. The first one is just lying on the ground under the entrance.
   
2. The second one can be bought at the shop in your castle, Winter Threshold. To get it, you have to finish the main quest Tuck's Emporium and upgrade your shop.
   
3. The third one comes from the druid Merlin - but only after you've collected and handed over all the tarot cards (see the Collect All Tarot Cards achievement).
   
4. The last runestone is on the Golden Forest map. Once you get the Elder Strygid Skull, head over to the marked spot and open the chest to collect it:
   

Find The Herons Fishing Pole
Return Ernest's missing Fishing Pole to him at the Lake in the Golden Forest.

While exploring the Golden Forest, you'll come across Ernest, who's looking for his lost fishing pole. To help him out, you'll need to find moles in the bottom-right corner of the map. One of them is using his fishing pole, but he won't return it unless you give the mole a jar of honey.

To grab the honey, head to the indicated spot and buy it:


Once you've got it, go back to the moles, trade the honey and return the fishing pole to Ernest.

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Find The Magpies Spectacles
Return Maggi's missing spectacles to her at Bogmire Forge.

On the Rift map, after a few quests, you'll get a sidequest from Maggi - she lost her spectacles and needs you to find them.

Just head over to the marked location and grab them:

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Deliver The Late Moledonalds
Deliver the late Moledonalds to Matt and Nath in their Outskirts bunker.

To complete this achievement, deliver the Moledonalds to the moles at the marked spot on the Outskirts map:

Their order can be found on the same map in this place:

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Collect All Tarot Cards
Collect all the tarot cards and deliver them to Merlin at their hut in the Rift.

They are 8 tarrot cards at total, which you'll need to find and deliver them to Merlin (the Rift map) in this spot:

Tarrot cards can be obtained:

1. Farmer card - on the Golden Forest map, sold by badger on the left side (underground).
   
2. Knight card - on the Rift map, in given spot:
   
   
3. Beggar card - on the Golden Forest map, sold by Ernest after finding fishing pole sidequest.
   
4. Council card - on the Rift map, sold by Maggie after finding spectacles sidequest.
   
5. Death card - on the Rift map, sold by Maggie after finding spectacles sidequest.
   
6. Druid card - on the Rift map, sold by the druid after upgrading smith quest.
   
7. Smith card - on the Crimson Keep map, sold by a seller at the docks.
   
8. Kingcard - on the Crimson Keep map, sold by a seller at the docks.

In order to complete achievements below, you need to complete every Boss and Infestation quest on specific map.

Complete Golden Forest Hunts
Complete all the hunts provided by the Sigrid in Nestminster.

There are 7 quests in total.

Hunts:

• Hunt the Slither Scale
  
• Hunt the Death March
  
• Court of Owls
  
• Scorch the Forest - available after finishing the game

Infestations:

• The Slither Scale Pit
  
• Death Marching
  
• WereOwls Fear to Tread

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Complete Outskirts Hunts
Complete all the hunts provided by the Mossbug Farm Elder.

There are 4 quests in total.

Hunts:

• The Root of the Problem
  
• Flocked Off
  
• Fear the Sky
  
• Scorch the Outskirts - available after finishing the game

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Complete Rift Hunts
Complete all the hunts provided by Short Tongue in Bogmire Forge.

There are 6 quests in total.

Hunts:

• A Wicked Web
  
• Hunt the Stealth Claw
  
• Requiescat in Pace
  
• Revenge of the Frog
  
• Scorch the Rift - available after finishing the game

Infestations:

• Tailspinner's Brood

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Complete White Whiskers Hunts
Complete all the hunts provided by Gray Ears in The Warren.

There are 2 quests in total.

Hunts:

• Ice Breaker
  
• Holes in the Ice

Build Level 3 Builder
Upgrade the builder to its highest level.

Upgrade the builder to level 2.
Probably the easiest one - base level is unlocked through the campaign, levels 1 and 2 are unlocked by basic resources and items from main quests).

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Build Level 3 Chef
Upgrade the chef to its highest level.

Upgrade the chef to level 2.
Base level is unlocked through the campaign.
Level 1 needs some basic resources.
Level 2 needs badger Marco (main quest) and some resources from Hunt missions.

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Build Level 3 Shop
Upgrade the shop to its highest level.

Upgrade the shop to level 2.
Base level needs some basic resources.
Level 1 needs some basic resources and items from mobs.
Level 2 needs some basic resources and items from Hunts.

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Build Level 3 Smith
Upgrade the smith to its highest level.

Upgrade the smith to level 2.
Every level is achieved by main quests items and some additional basic resources.

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Full Belly
Cook all meals at the Chef.

There are 3 meals in total:
#1: completed during the main story quest.
#2: needs three items sold by Marco after rescuing him (main quest).
#3: needs to upgrade the kitchen to level 3, ingredients sold by Marco.

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Craft A Level 3 Weapon
Craft a weapon from the level 3 section at the Smithy.

Self-explonatory - can be done after ugprading smith to level 3.

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Craft A Level 3 Cuirass
Craft a cuirass from the level 3 section at the Smithy.

Self-explonatory - can be done after ugprading smith to level 3.

These achievements are completely tied to the main story events. Make sure you snag them as you progress through the plot:

In The Ice Peaks Bind Them
Defeat Count Kazak at the top of Mount Cauldron.

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Win The Crimson Keep Tournament
Win the tournament in the Crimson Keep arena to win King Redgi's trust.

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Flying Turtle
Take a ride with Burtle in his flying contraption.

Last achievement you get after completed all achievements above:

Collect All Medals
Collect All Medals.