The one hundred and fifty-seventh issue of Elwood and first issue of Elwood High was released on May 10, 2017.
In this issue, Winny goes on a risky outing with her new friends, and conflicts with her mother over her new identity.
D.W., now calling herself Winny, is seen hanging out with two new friends, smoking cigarettes together. Winny starts to get anxious, and eventually leaves to her friends' disgust. Winny returns home, where she is sternly chastized by Jane, her mother. Winny leaves to her mother, telling her that she was just out studying. Jane sees through this fib when a pack of cigarettes falls out of Winny's pocket. Becoming flustered, Winny cries and screams to her mother, asking her to "butt out" and let her "live [her] life." Jane dials back, telling Winny that she just wants to keep her safe. While doing this, Jane calls her daughter D.W., which infuriates Winny. As Jane stands in exhausted defeat, Winny runs upstairs.
- Winny Read
- Jane Read
- Kate Read (photo)
- Arthur Read (mentioned)
- Maryann (mentioned)
- "Winny's friend (I)"
- "Winny's friend (II)"
- In the first draft of the issue, Winny's smoker friend shown in panels 2 and 3 was actually one of the Tibble Twins. However, both of the Tibble Twins were revealed to be killed by Pickles is Issue 098. Panel 5 was rewritten to remove the mention of Mrs. Tibble, and the character in panel 2 and 3 was altered to remove the Tibbles' likeness.