You will find below an extensive guide on how to obtain the Achievements available in the Bastard's Wound DLC for Tyranny.

I personally enjoyed the DLC a fair bit, despite certain mechanical flaws or apparent bugs. I however, found when I wasn't sure how to obtain a particular achievement, even following considerable use of search engines, I could find very little information on how to complete many of them. One achievement in particular required me to read an article written in German to obtain the necessary information.

Thus, in order to save others the difficulty of acquiring information, I wrote this guide. I hope it serves you well, and thanks for reading!

Description: Submit to Kyros at the end of Act 3.
How to Obtain: This is a very simple one. At the end of Act 3, when you've returned to the Mountain Spire, instead of casting an Edict on the Northern Empire, select the Dialogue option to Swear Fealty to Kyros.

Description: Wipe out Bastard's Wound after condemning it in dialogue with Mell.
How to Obtain: When first entering Bastard's Wound, you will talk to the Scribe Apprentice Mell. Choose the option to condemn the settlement to death for trespassing in the old walls. Following this you'll have to go around the entire Settlement of Bastard's Wound killing everyone (there are people inside two of the "dwellings" but the farm will be empty.). To obtain the achievement however you must also go back out to Cairn's Passage and kill the Beastwomen/Beastmen guarding the entrance to the town. As well you will need to enter the Bastard's Wound Oldwalls and kill all the sleepless (including Lexeme) and Reef-Talon.

Description: Complete Never Free.
How to Obtain: Simply complete Barik's Personal/Story Quest, getting him out of that armor whether he likes it or not. Keep in mind the Quest starts in Act 2, but cannot be completed till Act 3. There are two major requirements/branches for this quest. One is obtaining a Smith to release Barik from his armor. If you complete the Lethian's Crossing story-line during Act 2 you can get the Forge-Bound Master Zdenya to do it, or after talking to Forge-Bound Lohara you can learn of a Magic Smith operating in the Stone Sea. The second requirement is you must free Barik from Ashe's Aegis. This means you either need to kill Graven Ashe, or you must get him to submit to you. To do the latter you must simply be on the Disfavoured Route. After getting Ashe to submit, you speak to him, and using your new authority over the Disfavoured, discharge Barik from the Legion.

Description: Learn of the infighting in Bastard's Wound, and do nothing to resolve it.
How to Obtain: Possible regardless of who you sided with in Bastard's Wound (Unless it was the law, in which case you already killed everyone.). After confronting Reef-Talon and returning to Bastard's Wound, you'll find Scribe Mell, Jaspos, and Wagstaff (and possibly Reef-Talon if you've chosen her route) arguing by the portal. After asking them "What is going on here?" they'll explain they each have mutually exclusive plans for Bastard's Wound. Among the Dialogue Options will be the option [Just walk away]. Select this, and then the bottom option (something to the effect of "you're lucky I haven't condemned this settlement already"). After the leaders have walked away, you must leave Bastard's Wound in order to obtain the achievement.

Description:Share an uncomfortable moment with a party of four or more (Sirin doesn't count).
How to Obtain: After viewing the final scene/dialogue for Lantry's Personal/Story Quest, choose to click on the berry bush again and go for another round of those hallucinogenic berries. As stated above Siren doesn't count. In addition DO NOT BRING SKILLS-IN-SHADOW. At the end of the scene that gets you the achievement, all members of the party will strip off all their gear. There is a bug which causes Kills-in-Shadow to remove her Artifact "Infused Shadows" and it cannot be re-equipped. A secondary note, all companions, or at least active party members, may need to be at Loyalty 3 in order to obtain this achievement.

Description: Perform a Critical Miss wielding a slab of meat.
How to Obtain: Only possible if you've decided to condem the settlement of Bastard's Wound and kill all the inhabitants.

After killing one of the Merchants, looting their corpse will yield a one-handed weapon "Slab of Meat". Equip this weapon to the Main Character/Avatar (I've heard of people giving it to Verse and not getting the Achievement) and continue to kill the inhabitants of Bastard's Wound. It'll pop up eventually.

Description: Resolve the troubles of the Bastard's Wound without slaying the resident havoc.
How to Obtain:

WARNING: Only obtainable on the Reef-Talon route in Bastard's Wound.

After completing the initial quests from Jaspos and Wagstaff (Obtaining the Tools for Jaspos and dealing with Sage Phoibe for Wagstaff), instead of talking to either of themand beginning their quest to hunt for Reef-Talon, go to Scribe Mell and he will put you onto the quest "History of the Old Walls". When you reach Sage Lexeme, tell her that Mell sent you, and instead of leading you into the next room, she'll simply give you the Tanza Keystone and tell you where Reef-Talon is. After that you simply have to complete the Quest-line without entering Lullaby's room.
Note that while you have to be on Reef-Talon's path to complete this Achievement, you do not actually have to side with Reef-Talon when selecting the Leader of Bastard's Wound.

Description: Complete Verse's Side-quest and have her usurp the Voices of Nerat.
How to Obtain: Only possible during the Scarlet Chorus Route. Require's that you've first completed Verse's Personal/Story Quests "The Fire Inside" and "The Third Degree". After killing Graven Ashe, when The Voices of Nerat ask for you to sacrifice one of your companions to him, simply offer up Verse as your tribute.

Description: Slay a foe with a slab of meat.
How to Obtain: Only possible if you've decided to condemn the settlement of Bastard's Wound and kill all the inhabitants.

After killing one of the Merchants, looting their corpse will yield a one-handed weapon "Slab of Meat". Equip this weapon to the Main Character/Avatar (I've heard of people giving it to Verse and not getting the Achievement) and continue to kill the inhabitants of Bastard's Wound. You'll obtain it as soon as the Main Character/Avatar slays an enemy.

Description: Place Wagstaff in a position of authority over the Bastard's Wound.
How to Obtain: At the end of the main quest-line for Bastard's Wound, select Wagstaff to be the leader of the Settlement.

Description: Slay all of the Sleepless in Bastard's Wound.
How to Obtain: To obtain this Achievement you must also meet the requirements for "They Sort of Deserved it...". Firstly you must go through the Bastard's Wound Oldwalls and kill all the Sleepless there, including the the NPC Sleepless and Lexeme.

To get "They sort of deserved it..." you need to tell Reef-Talon "You're going back to the Wound one way or another", then you need to tell her "You're running from your guilt" TWICE. This means you need to pick the option twice. Tell her killing them is the only way. After the second time you'll get the opportunity to yell at her with an Athletic Check, then you'll get the chance to lie to her with a Subterfuge check. After that she'll go about killing all the Sleepless in "The Abyss" excluding Lexeme.

WARNING : Currently if you're on the Quest/Route to make Reef-Talon the leader of Bastard's Wound (Quest Name: History of the Oldwalls), the game will bug out. This results in a Lexeme who refuses to die. More specifically you keep killing her and it doesn't count. I looted her corpse not once, but twice, and she still managed to show up in front of the final mural beside Reef-Talon.

Description: Appoint Jaspos to a position of authority over the Bastard's Wound.
How to Obtain: At the end of the main quest-line for Bastard's Wound, select Jaspos to be the leader of the Settlement.

Description: Defeat three groups of Sleepless below Bastard's Wound.
How to Obtain: Refers to the "Sleepless" enemies sometimes found among a group of Bane in the Bastard's Round Oldwalls. If you clear out all the enemies between the three maps you should obtain this Achievement.

Description: Complete the game with Barik freed out of his armor but trapped in a cage of abuse.
How to Obtain: Complete Barik's Personal/Story Quest, freeing him from his armor. When a random event procs where your party members begin complaining about how Barik smells, do not let him clean up/bathe. Then simply complete the game.

Description: Install Reef-Talon in a position of authority over the Bastard's Wound.
How to Obtain: After completing the initial quests from Jaspos and Wagstaff (Obtaining the Tools for Jaspos and dealing with Sage Phoibe for Wagstaff), instead of talking to either of them, and beginning their quest to hunt for Reef-Talon, go to Scribe Mell and he will put you onto the quest "History of the Old Walls". When you reach Sage Lexeme, tell her that Mell sent you, and instead of leading you into the next room, she'll simply give you the Tanza Keystone and tell you where Reef-Talon is. Tell Reef-Talon that Lexeme thinks her powers can be trained.
When speaking to Reef-Talon in front of the Mural, select options that imply positive things about the Beastwoman in the painting. When asked to tell Reef-Talon about the other Murals in the Oldwalls, tell her the following:

1. Beasts entering oldwalls from top mural "The oldwalls once had many different inhabitants..."
   
2. Oddwalls held up by beast mural "Beastmen were meant to fight bane..."
   
3. Hand-print mural "Many of the prints were formed with essence..."
   
4. "The beastwoman is showing her dominance..."
   
5. (Lore) "What you're seeing is a historical record..."

After this she will agree to return to Bastard's Wound. At the end of the main quest-line for Bastard's Wound, select Reef-Talon to be the leader of the Settlement.

Description: Trick Reef-Talon into inadvertently wiping out her loved ones in Bastard's Wound.
How to Obtain: To get this achievement, when confronting Reef-Talon in her room in "The Abyss" you'll need to tell her "You're going back to the Wound one way or another", then you must tell her "You're running from your guilt" TWICE. This means you need to pick the dialogue option a second time after the first. Tell her killing them is the only way the first time, after the second time you'll get the opportunity to yell at her with an Athletic Check, then you'll get the chance to lie to her with a Subterfuge check. After that she'll go about killing all the Sleepless in "The Abyss" excluding Lexeme.

WARNING : Currently if you're on the Quest/Route to make Reef-Talon the leader of Bastard's Wound (Quest Name: History of the Oldwalls), the game will bug out. This results in a Lexeme who refuses to die. More specifically you keep killing her and it doesn't count. I looted her corpse not once, but twice, and she still managed to show up in front of the final mural beside Reef-Talon.

Description: Complete all available quests and sidequests in the Bastard's Wound.
How to Obtain: The quests in Bastard's Wound are all pretty straight forward to completely, mostly just a lot of running around. Finding all of them however is not.

Once you've completed Jaspos's Quest to obtain the Gravelight Tools, and Wagstaff's quest to kill Sage Phoibe and take her belongings, go around the settlement talking to the various NPCs.
Eisly will give you the sidequest "Midnight Wanderer". Rostrom Lenk will give you the sidequest "Gambler's Ruin".
After completing these, continue with the Bastard's Wound primary quest-line. When reaching Lexeme and obtaining the Tanza Keystone, find all the remaining Texts, and then return to her. After speaking with Lexeme and sentencing her, continue to Reef-Talon. Complete the Bastard's Wound primary quest-line.

Description: Complete Lantry's Companion Quest.
How to Obtain: Complete Lantry's Personal/Story Quest.

Description: Complete Verse's Companion Quest.
How to Obtain: Complete Verse's Personal/Story Quest.

Description: Throw a villager into the well at night in South Haven.
How to Obtain: During the quest to obtain Jaspos's Tools, you will be sent to the village of South Haven. When speaking to Cassandra, [lie] and tell her that the tools are rightfully hers. Afterwards speak to Capteron. Convince him that you need to closely inspect the Forge-Bound and then select the dialogue option to "wait till nightfall". Afterwards Stealth, walking around the Forge-Bound keeping watch, and go into town. You'll find an NPC standing by the wall. Talk to him and choose to push him into the well.