Thanks for the chapter!
Seems Anne has picked up that MC has changed in some ways while still the same in others. It's good MC isn't taking Anne helping her out so much for granted anymore and wants to share things with Anne too. As for good/bad endings with Alan, nothing happens to Katarina, but good ending has Mary, who loves Alan very much, tearfully bow out and he marries Maria. Bad ending he's just friends with Maria and marries Mary. As for the snake seems MC needs to work a lot more on the quality. In any case, at least she helped break the ice between the two brothers, but seems like she's attracted Gerald's interest even more. Hopefully this route doesn't have him telling her mother about it and getting her in big trouble.
In the LN version when started at age 8 instead of 15 there's a side story about Anne's engagement. I think Anne was the result of what was supposed to be a one night stand between her father and mother, (basically lord of the house having his way with the staff,) resulting in her and her mother living in a distant house with extremely rare visits from her father. One night the house caught fire killing the mother and leaving a horrible burn scarring Anne's back. This is a big issue as society is very finicky about scars or wounds on women, (guess it's considered cool for guys,) and would greatly hinder Anne's marriage prospects. After recovering enough to work she got a job with Duke Claes. Engagement was with a middle aged noble with a bad reputation who was going to pay a lot of money to her father so could marry her. Daddy Dearest was taking her to the carriage to sell Anne off with her in shock and wondering what she could do to get out of it without causing trouble for Duke Claes when Katarina interfered. After hearing about it Duke Claes made a few arrangements to cancel the engagement and prevent her father from selling her out again.
@Kampfarsch It's both similar and different due to it happening in the same world but when she's 15 instead of 8. Her stepbrother Keith doesn't like or trust her, acts like a playboy instead of a gentleman, and any issues she helped the other characters through when started at 8 still exist. So before this chapter Alan was still oversensitive about Gerald being better than him at practically everything and hadn't had a friendly conversation with him in years. While getting along with Mary better it's not to the point in 8 year old start where Mary is head over heels for MC resulting in her training to be best lady for MC and not Alan who she's got a mutual agreement with not to break up the engagement due to mutual lack of interest in order to avoid talks or dealing with future prospective suitors cutting into their time with MC. Also, Sienna never appeared in the earlier start.