PSYCHO-PASS: Mandatory Happiness

This achievement is for reaching the "Light and Shadow" route in Nadeshiko Kugatachi's story.

First, start as Nadeshiko Kugatachi.

Case: 01 / 2 -- Inquire
Case: 02 / 2 -- Inquire about friendships
Case: 01 / 4 -- Head to the mall
Case: 01 / 2 -- Take the supplement
Case: 01 / 3 -- It's possible
Case: 01 / 4 -- Ask Kagari and Kunisuka to come

Chapter 1 End

Case: 01 / 2 -- Take the supplement
Case: 02 / 2 -- Analyze area stress level with Ginoza
Case: 03 / 3 -- Perform a balanced search
Case: 02 / 3 -- Give order to infiltrate
Case: 02 / 2 -- I did not manage to stop Tsurugi
Case: 02 / 2 -- Don't take the supplement
Case: 01 / 3 -- Accept it

Chapter 2 End

Case: 01 / 2 -- Take the supplement
Case: 01 / 2 -- Secure the fire extinguisher
Case: 02 / 2 -- Join Akane's rescue team
Case: 04 / 4 -- Wait for Molotav cocktails to deplete
Case: 02 / 2 -- Continue interrogation
Case: 03 / 3 -- Give order to back down
Case: 03 / 3 -- Try to force your way through
Case: 02 / 4 -- Push cabinet to seal the exit route
Case: 02 / 2 -- Don't take the supplement
Case: 02 / 3 -- Leave and recover naturally
Case: 02 / 2 -- Yes

Achievement

Light and Shadow
(Nadeshiko path)

So it seems you can have a private conversation with Masaoka.

This seems to be when some of your options

See TA walk-through for details.