I ran into a similar issue this year with 2023 Premier. You have to follow a very specific workflow to force the W2 question to trigger. For any investment that is an ESPP you must:
1. Select "Employee stock purchase plan (ESPP)" in the initial individual investment sale workflow screen.
2. After completing the rest of the initial screen and clicking continue, you will reach the "Adjust your cost basis to ensure your best outcome" screen. On this screen you must select "I can't find it and need help". This will take you through the step by step workflow where you enter additional information such as what employer it was related to, discount, and details from the form 3922.
3. After completing this for all stocks and clicking through the rest of the Investment income workflow, you will be presented with the W2 questions.
I found it very unintuitive. If you select "I found my adjusted cost basis" it will not trigger the rest of the ESPP workflow or the W2 question. I only discovered this through a few hours of trial and error.
