Pentiment

There are a lot of dialogue checks in the game but it is incredibly easy to accidentally lose a lot of them through the way you talk around town. I managed to fail a few and came out of my first playthrough having not completed five. It seems you have to do them all in ONE PLAYTHROUGH.

I'm going to use this solution to try and compile the checks available to you and try to put the appropriate directions under them, be aware that the game catalogues "this will be remembered" choices and uses them to make these checks. So if one pops and the character seems to look angry it may be worth a reload.

I'll try not to include explicit spoilers:

ACT I

- Iluminata keeping the book.
Location: Unmissable, Scriptorium.
An Orator helps this immensely, but just agree to collect the books for her without any fuss and be polite and efficient and she should agree.

- What is Martin doing?
Location: Unmissable When heading back from abbey after dinner with the Lord.
Rapscallion background, Tell Martin not to work to hard, Don't talk to him outside the guest house.

- Worjslav and the cellar.
Location: Abbey Kitchen during investigation.
Defend Piero, Don't apologise to Abbot for interrupting.

- The Abbots permission to dig the grave.
Location: Abbey big garden after pursuing Fenec's case in investigation.
Don't engage the lord at dinner, be respectful to the Abbot at all times, and don't ask for the Gertners rent until after this check.

ACT II

- Otto's Secret.
Location: Unmissable, when you go to the Town Commons for the first time.
Never say the abbey does any good work around Otto, have dinner with his family for extra plusses.

- Dr Werners information.
Location: Investigation at the inn, upstairs
I got this even after breaking his nose (which is a minus). A background in law helps massively, as does not showing off to the other men at the table. Make sure to mention Werner was first at the scene and that he saw a shadowy figure.

- Hanna's revelation
Location: Golden Inn, upstairs, after investigating the shrine in the forest.
Don't look down on her for her infidelity, if you have dinner with Nico and the family make sure to disagree with Otto's ideas.

- Brigite revealling Martin's secret.
Location: Martin's farm (bottom right of the map), Brigite.
Be complimentary about the changes in Martin, Don't lie to her about your reasoning for asking questions. Don't Accuse Martin of murder in act 1.

-Accuse Martin.
Location: , Martins farm.
Orator background, get knocked out in the bar fight, Tell Martin it's good he's returned, confront him about his lost scar (that Stoltz' check will confirm) and said Brigita admitted he's not Martin (which her check confirms).

-Convincing Karl to let you in the crypt
Location: Have a meal with Illumianta the Prioress.
Orator Background seems to get this one in the bag.

- Convincing Caspar to leave.
Location: Unmissable, Just before naming the suspect.
Orator background, DO NOT encourage Caspar to learn from your mistakes as an artist at the start of the act. Reprimand Caspar on Saint Johns eve. DO NOT reassure Caspar when the Mob comes.


THIS IS A WIP. If you have any other dialog checks to add, or points that will make suceeding these more efficient please comment so we can update and make sure this details everything. Good luck!

For unlocking the achievement you have to persuade different people in Tassing five times. You can miss this achievement easily, because finding or saying the right things are very important for the persuasion. You can get this achievement in the first chapter, but you can also miss it through the whole game. Like other solutions said you have to do ALL FIVE PERSUASIONS in one playthrough.

So that you are not missing any persuasion I want to collect in this solution as many persuasion checks as possible. I found a lot of dialogues in Act 1-3. If I already miss something, please write a comment and I hope I can update this solution. If I forget editing this solution I would recommend you to take a look at the Pentiment-Fandom (https://pentiment.fandom.com/wiki/Pentiment_Wiki), where some Persuasion-Checks and modifiers are listed on different pages (like character pages etc.).

For people, which are interested in: My Andreas was in Italy, has a Bookworm-background and studied imperial law. He also has an Orator and Logician background. In the second act he travelled to France. If you want to persuade a lot of people, I really recommend you the Orator-background.
In the second act I gave Magarete the "Philobiblion" as present.

If there are any spelling, typing and grammar mistakes I want to apologize in advance. English is not my native language and I am usually writing solutions in my native language. I did my best to translate this as good and adequately as possible.

ACT 1:

Sister Illuminata and the books
After your first work shift in the skriptorium Sister Illuminata will ask you to collect some books for her. After returning two books you find a controversial book, which Sister Illuminata wants to destroy. You can persuade her for not destroying it. If you are clever enough you can persuade her three times. At first you can persuade her two times that the book is not going to be destroyed:

• Bookworm-background (+5)

• Pretend to not know about Ferenc's books (-1)

• Said books should be cared (+1)

• Asked for forgiveness for keeping books (+1)

• Offered to help Illuminata enthusiastically (+2)

• Offered to help Illuminata relunctantly (-2)

• Latinist: Quoted the Aeneid from memory (+1)

• Quoted Christine de Pizan to argue women have opportunities (+1)

• Said losing a book was like losing a limb (+1)

• Claimed that yo love books (+1)

• Books shouldn't be destroyed! (+2)

• Declared Father Matthias was reckless (-1)

• Sympathized with Father Matthias (+1)

• Yelled that the church was wrong to condemn the book

I've got 11 pluses for persuading Illuminata: Bookworm, Books should be cared, asked for forgiveness, help enthusiastically, losing book was like a limb, claimed you love books and books should be not destroyed. There is also a Theology-background opportunity which listed at the Fandom-Page of Illuminata

Offer Illuminata to keep the book
After the three persuasions (one of them will fail I think, but I am not sure) you can offer Illuminata to keep the book:

• Orator background (+3)

• Offered to help Illuminata enthusiastically (+2)

• Offered to help Illuminata relunctantly (-2)

• Imperail law: Offered unsolicited legal adive ... (-1)

• Imperial law: ... and then explained your legal education (-2)

• Imperial law: ... but you apologize (+1)

• Pretend to not know about Ferenc's books (-1)

• Asked for forgiveness for keeping books (+1)

I've got 9 pluses for persuasion: Orator-background, help enthusiastically and asked for forgivenesss.

Get a friendly greeting from Martin
The next kind of persuasion is getting a friendly greeting from Martin on the next day. It depends how you behave Martin previously.

• Rapscallion-background (+3)

• Called Martin an idiot (-3)

• ... but apologized for it later (+1)

• Told Martin not to work too hard (+2)

• Told Martin to help his family (-2)

• Fave Martin thieving advice (+3)

• Invited Martin to supper with the boys (+1)

• Said you'd put Martin in your masterpiece (+2)

• Martin ended the conversation mad at you

You only need at least 3 pluses for a friendly greeting: Say Martin not to work too hard and invite him for lunch with the guys.

Impress Baron Rothvogel
After the friendly or unfriendly greeting of Martin you meet Michlaus and talk about Rothvogel. Here it depends, how you behave towards the Lorenz. If you are successful, you will get a pin.

• If you meet Lorenz the first time say to him, that you are honored because of his invitation for taking a walk to the abbey (+1)

• Complained about being late to the abbey (-1)

• Said to him, that the ideas of Martin Luther are fascinating (+1)

• Sharing occult lore (Occult-background) (+1)

• Respectfully adressed the baron in the scriptorium (+1)

• Said you have been already invited for dinner (-1)

• Refuse the debate about Martin Luther (Orator) (-1)

• Refuse the debate about Martin Luther (-2)

• Accept the debate about Martin Luther (+3)

I impressed Lorenz with only 3 pluses and 1 minus: Honored for invitation to walk, Martin Luthers ideas are fascinating, talk to him respectfully in the scriptorium and refuse the debate about Martin Luther.

Get Wojslav to let you into the cellar
If you don't want to persuade Wojslav you can have lunch with Adam and Vacslav alternatively for finding Wojslavs little secret. If you have the information, you can blackmail him.

• Orator-background (+3)

• Defend Piero (+1)

• Don't ask for forgiveness (+1)

• Ask for forgiveness (-1)

Get the abbots permission for digging the grave

• Logician-background (+3)

• Do not mention Ferencs name (+0)

• Lie to Gernot, that you did not investigate in the abby (+1)

• Do not debate with Lorenz at dinner (+1)

• Debate with Lorenz at dinner (-1)

• Objected to Piero's assumed guilt (-1)

Gernot is really hard to persuade, but you need at least 5 pluses: Logic-background, not mention Ferenc, lie to Gernot and don't start the debate at dinner

Persuade Ottilia keeping the cross
If you are going to investigate Ottilia, you have to help her by collecting wood and hanging pictures. After this she asks you taking off the cross and you can ask her, whether she is aware of her decision and if she wants to keep it.

• Orator-background (+3)

• Steal the wood (+1)

• Concerns of Ottilias well-being after the minigame (+1)

You only need 4 pluses for persuading Ottilia, but you can earn all 5 pluses in one playthorugh

Persuade Linhart for having lunch/dinner
After starting your investigation you can interrogate Linhart (and follow him). After this you can convince him having lunch with you.

• Orator-background (+3)

• Don't harass Linhardt because of the dispute with Lorenz (+1)

You only need this 4 pluses for persuading Linhart.

Persuade Agnes to get Linharts murder motive
Linhardt is not really communicative, instead for interrogating him, you can ask his wife Agnes- But Agnes will only talk, depending on your behaviour towards her, Linhardt and the townspeople.

• On the second day you meet Agnes & Ulrich. Show your interest for the Pfeiffers (+1)

• At the end of the conversation with Ulrich and Agnes tell Agnes that you are praying for Helena (+2)

• Take a meal with Agnes and Linhart (+1)

• Tell Agnes while eating, the townspeople could be happy for having her (first ask about Doktor Stolz) (+2)

• Ignore the warning about Lenhardt Müller (-2)

You need at least six pluses and no minus to unlock the murder motive of Linhart. I would recommend you all of the mentioned points.

Murder suspects
At the end of Chapter 1 you express your suspicion to Jakob. After you mentioned all of them (or which you want to mention) you can aks Jakob if you give him a final advice. Only if you was very polite, he will hear you out:

• Orator-background (+3)

• Said your name politely (+2)

• Mentioned you did not like aristocrats (-1)

• Clarified you have no problems with aristocrats (+1)

You need at least six pluses for giving Jakob your final advice.

ACT 2:
Convincing Otto
At the beginning of Act 2 you meet Otto in the city and listen to his speech. After the speech you have a conversation with him, Eva and Klara. The success of this persuasion will depends which answer you say to Otto in the first chapter after lunch:

• Understand why many people hate the abbot (+3)

• Said that the abbey does a lot of good things for Tassing (-3)

You need 3 pluses for this persuasion Otto, which you can miss easily, if you gave him the wrong answer.

Convince Ursula to embrace/reject the old ways
After the return to Tassing you get an invitation by the Gertners for dinner. After that you can talk to Ursula and embrace or reject the old ways. Depending which travelling stories you tell her, you succeed or fail (embrace points | reject points):

• Occultist-background | Theology-background

• Told the background-story (girl with oranges, basilisk or cat ad cradle) in Act 1 (+1 | -1)

• Told the story of the tired artist and the little girl (-1 | +1)

• Invoked God during the Gertners' meal (-1 | +1)

• Mentioned you enjoy reading book (+1 | -1)

• Told the backgorund-story (giant Basajarau, Wawel Dragon, Melusine or Yeth Hound) in Act 2 (+2 | -2)

• Told and ordinaty travel story (-2 | +2)

You only need 3 pluses for success, just tell Ursula your background stories for embracing her to the old ways or tell her ordinary stories for rejecting them.

Persuade Karl to clean the crypt
Since the monks are hiding in the library you have the opportunity to dine with them, if you ask Mother Illuminata. On the way to the secret entry to the library you meet Karl an convince him to clean the crypt.

• Orator-background (+3)

• Make him a compliment for the fire (+1)

• Encourage Anton to obey him (+1)

I recommend to collect all of the mentioned pluses. Don't forget to talk Karl at the feast.

Persuade Josua in the golden Hand
After starting your investigation you can spend a beer for a lot of people and especially tourists in the golden hand. You have the opportunity to get a few hints from Josua and his wife, some tourists from Mühldorf after the brawl. Here it depends what kind of things you said at your toast at the beginning of this investigation:

• Said something nice about Otto (+1)

• Expressed your grief about his death (+1)

• Rationalize an act of God(-1)

• Asked for help for your investigations concerning Otto's murder (+1)

You need 3 pluses and no minus for persuade Josua and his wife to get a hint about Martin and his changing. Always be nice to them and mention only the good sides of Otto.

Persuade Werner at the inn
After starting your investigation you can spend a beer for a lot of people and especially tourists in the golden hand. You have the opportunity to get a hint from Werner after you speaking to him and his friends:

• Imperail law-background (+3)

• Kept out of discussion of Plintius' natural history (+1)

• Mentioned Werner's role by finding Ottos corpse (+2)

• ... two times (+1)

You need at least 4 pluses for persuading Werner and get a hint about Martin as reward. Always be polite to Werner and let him look well in front of his friends.

Persuade Brigita
While your return to Tassing you will notice that Martin is back and he has changed a lot. You can talk to Brigita to get another hint for his change:

• Praised Martin's changing (+1)

• Only said good things about Martin's return (+2)

You need at least the 3 pluses to get the final hint that something is wrong with Martin.

Accuse Martin
You can blame Martin with his secret after collecting enough hints.

• Orator background (+3)

• Asked him about his disappeared scar (+1)

• Asked if he knew Jobst Färber (+3)

• Caught him knowing about Jobst brawl (+1)

• Pointing out that Martin does not sneeze (Chapter 1) (+1)

• ... and his mother mentioned it (Chapter 1 after his disappearance) (+1)

• Said that Brigita has admitted that he is not Martin (+2)

You need at least 8 or 9 pluses for learning the truth about Martins disappereance, return and his change, which is finally his murder motive. You only have to collect all hints and you need to confront him for beeing successfully.

Persuade Hanna
After investigating the roman aqueduct you get a possible murder motive of Hanna, the lady who is running the inn. You also discover that Lenhardt and Hanna have an affair. You can confront her with your investigations:

• Praised her inn (+1)

• Didn't agreed with Ottos ideas while lunche/dinner (+1)

• Agreed with Ottos ideas while lunche/dinner (-1)

• Told Hanna that Niko does not know anything about her affair (+2)

• Told Hanna that Niko does know about her affair (-2)

You need at least 4 pluses for beeing successful. I also recommend you to dine with Hanna an her family for getting the last plus for not agreeing with Otto's ideas.

Persuade Niko
You can also persuade Niko and confront him with the affair of his wife.

• Show compassion (-2)

• Called him pathetic (+2)

• Said you knew that Niko knew about Hanna and Lenhardt (+1)

You need 3 pluses for persuading Niko, reproach him in this conversation about his wife and marriage.

Convince Caspar to leave Tassing
At the end of the second act you have the opportunity to convince Caspar for leaving Tassing. Instead of beeing nice and caring to Caspar you have to be rude and embittered.

• Orator-background(+3)

• Told Caspar to expect a life of misery as an artist (+3)

• Encouraged Caspar to learn from your mistakes as an artist (-3)

• Reprimanded Caspar on Saint John's Eve (+2)

• Showed concern for Caspar on Saint John's eve (-2)

• Lost all your money at Lansquenet (+2)

• Beat everyone at Lansquenet (-2)

• Scolded Caspar after falling into the cistern (+2)

• Cared for Caspar after you fell into the cistern (-2)

• Didn't reassure Caspar when the ob came (+2)

• Reassured Caspar when the mob came (-2)

If you always be rude and careless to Caspar he will leave Tassing, but this kind of behaviour will alienate Andreas and him.

ACT 3:
Like I mentioned, I gave Magdalene the Philobiblion as a gift. In the last act you can choose the last three backgrounds. I choose the backgrounds Polyglot, Haggle and Tinker as backgrounds. Act 3 has less persuasions like the two before.

Persuade Black Til, helping you to get into the mine
To find somethin about the early history of Tassing, you have to ask a few villagers, one of them is Black Til. He gives you the clue, that you can find some things in the mine.

• Haggle-background (+3)

• Be curious about the daily life of the pagans (+1)

• Trying to lie to him (-1)

• Dedicate to the success of the mural (+1)

• Said, that you want, that your father should be proud of the mural (+2)

You only need 4 pluses for persuading Till, who will give you the hint, that you should ask the twins.

Convince Krafft, doing the education/apprenticeship
Krafft is the son of Brigita and "Martin" and is going to be a stonemason. Agnes, his grandmother, wants a better education for him, so you have the opportunity convincing him to leave Tassing for his education or to stay there.

• Teased Krafft (Barbs-background) (-1)

• Flirt with Krafft (Flirt-background) (+3)

The only possibility, persuading Krafft is the Flirt-background, because you need 3 pluses. If you have not the Flirt-background use inverted psychology (this is not a persuasion success): Say to Krafft to leave Tassing and he will stay there, ask him to stay and he will start the apprenticeship.

Convince Sister Susanne to stay with the Poor Clares
For the second part of the mural, you can visit Kiersau or what is left of it. You meet, beside some old fellows, Susanne, who is involuntary member of the Poor Clares. You can convince her to stay with them:

• Haggle-background (+3)

• Invited Susanne to disobey Mother Fraziska (-1)

• Told Susanne being a nun is an honor (+1)

• Told Susanne convent life isn't that bad (+2)

• Discussed how Matilda and Wojslav left Kiersau (+2)

• Agreed that being forced into the convent is wrong (-1)

• Suggested Susanne leave the convent (-2)

• Translated the chapel inscription (Polyglot-background) (-1)

I persuaded Sister Susanne with at 10 pluses, but I think you need less.

Convince Sister Susanne to leave the Poor Clares
You can also convince Susanne to leave the Poor Clares:

• Haggle-background (+3)

• Invited Susanne to disobey Mother Fraziska (+1)

• Told Susanne being a nun is an honor (-1)

• Told Susanne convent life isn't that bad (-2)

• Discussed how Matilda and Wojslav left Kiersau (-2)

• Agreed that being forced into the convent is wrong (+1)

• Suggested Susanne leave the convent (+2)

• Translated the chapel inscription (Polyglot-background) (+1)

I persuaded Sister Susanne with at 10 pluses, but I think you need less

These were all persuasions, I found in my several playthroughs and thanks to the fandom. I am going to add new pluses and minuses if I find new persuasion opportunities.
Wish you good luck persuading Tassing :)

Dialogue checks are special dialogue options based on your standing with the npcs.
It shows you the breakdown of your prior interactions. If the Option is Blue it counts.
The first one you will encounter is with Martin.
Basically try and be as nice to everyone as possible and you will get this naturally as theres lots more than 5 of these checks in the game.