In 2015, Woodley reprised her role as Tris in The Divergent Series: Insurgent, the second installment in The Divergent Series.
Her performance once again received critical acclaim, with Daniel M. Kimmel of New England Movies Weekly writing, "Woodley does solid work here as she's done elsewhere, and continues to be someone to watch."
Despite a more negative critical reception than the previous film, Insurgent was commercially successful, making nearly $100 million in its worldwide debut and grossed $295.2 million worldwide.
She reprised her role again in the penultimate film of the series Allegiant (2016).
The film, however, was poorly reviewed by critics and a box-office bomb.
Lionsgate had planned for the final film in the series to be made for television, but Woodley announced that she would not be a part of it.
She next starred opposite Joseph Gordon-Levitt in Oliver Stone's biographical thriller Snowden (2016), in which Gordon-Levitt portrayed Edward Snowden.
Owen Gleiberman's review said that Woodley "gives a performance of breathtaking dimension: As the movie goes on, she makes Lindsay supportive and selfish, loving and stricken."

Starting in 2015, Woodley took a break from filming for nearly a year, stating in a later interview that she "had hit a wall with acting."
From 2017 to 2019, Woodley starred as a sexual assault survivor, alongside Nicole Kidman and Reese Witherspoon, in two seasons of the HBO drama series Big Little Lies.
She was nominated for an Emmy and Golden Globe Award in 2017 for Best Supporting Actress in a Limited Series or Movie and Best Performance by an Actress in a Supporting Role in a Series, Limited Series or Motion Picture Made for Television respectively for her role.
She also starred in and produced the biographical film Adrift (2018), with Baltasar Kormákur as director.
Her performance as Tami Oldham Ashcraft, a real-life sailor who was stranded at sea after a storm, with Daniel Feingold from WSVN calling her work "Oscar-worthy".
Woodley was awarded the Rising Star Award during the 2018 Deauville Film Festival.

In 2019, Woodley starred in the romantic drama Endings, Beginnings alongside Sebastian Stan, Jamie Dornan and Matthew Gray Gubler.
She also joined the romantic drama film The Last Letter From Your Lover, which began production in Mallorca, Spain and United Kingdom in mid-October 2019.
Woodley will executive produce the film alongside co-star Felicity Jones.
The film is directed by Augustine Frizzell.
In November 2019, she joined the cast of real-life drama film Prisoner 760.
The film will star Jodie Foster, Tahar Rahim and Benedict Cumberbatch and began filming in South Africa on December 2, 2019.
She was also cast in Girl Named Sue, a film based on the true story of Sue Webber-Brown, a DEA agent who created the Drug Endangered Children (DEC) protocol.
She will next star in Misanthrope, an upcoming thriller centered on a talented but troubled cop who is recruited by the FBI to help profile and track down a serial killer.
The film is set to be directed by Damián Szifron.
Woodley will serve as a producer on the film.
She joined Shia Lebeouf and Robert De Niro in the upcoming crime drama After Exile, with Joshua Michael Stern as director.
 She is attached to star in animated feature Arkie and romance film No Baggage, which are in pre-production and development respectively.
In 2015, Woodley reprised her role as Tris in The Divergent Series: Insurgent, the second installment in The Divergent Series. Her performance once again received critical acclaim, with Daniel M. Kimmel of New England Movies Weekly writing, "Woodley does solid work here as she's done elsewhere, and continues to be someone to watch." Despite a more negative critical reception than the previous film, Insurgent was commercially successful, making nearly $100 million in its worldwide debut and grossed $295.2 million worldwide. She reprised her role again in the penultimate film of the series Allegiant (2016). The film, however, was poorly reviewed by critics and a box-office bomb. Lionsgate had planned for the final film in the series to be made for television, but Woodley announced that she would not be a part of it. She next starred opposite Joseph Gordon-Levitt in Oliver Stone's biographical thriller Snowden (2016), in which Gordon-Levitt portrayed Edward Snowden. Owen Gleiberman's review said that Woodley "gives a performance of breathtaking dimension: As the movie goes on, she makes Lindsay supportive and selfish, loving and stricken."
Starting in 2015, Woodley took a break from filming for nearly a year, stating in a later interview that she "had hit a wall with acting." From 2017 to 2019, Woodley starred as a sexual assault survivor, alongside Nicole Kidman and Reese Witherspoon, in two seasons of the HBO drama series Big Little Lies. She was nominated for an Emmy and Golden Globe Award in 2017 for Best Supporting Actress in a Limited Series or Movie and Best Performance by an Actress in a Supporting Role in a Series, Limited Series or Motion Picture Made for Television respectively for her role. She also starred in and produced the biographical film Adrift (2018), with Baltasar Kormákur as director. Her performance as Tami Oldham Ashcraft, a real-life sailor who was stranded at sea after a storm, with Daniel Feingold from WSVN calling her work "Oscar-worthy". Woodley was awarded the Rising Star Award during the 2018 Deauville Film Festival.
In 2019, Woodley starred in the romantic drama Endings, Beginnings alongside Sebastian Stan, Jamie Dornan and Matthew Gray Gubler. She also joined the romantic drama film The Last Letter From Your Lover, which began production in Mallorca, Spain and United Kingdom in mid-October 2019. Woodley will executive produce the film alongside co-star Felicity Jones. The film is directed by Augustine Frizzell. In November 2019, she joined the cast of real-life drama film Prisoner 760. The film will star Jodie Foster, Tahar Rahim and Benedict Cumberbatch and began filming in South Africa on December 2, 2019. She was also cast in Girl Named Sue, a film based on the true story of Sue Webber-Brown, a DEA agent who created the Drug Endangered Children (DEC) protocol. She will next star in Misanthrope, an upcoming thriller centered on a talented but troubled cop who is recruited by the FBI to help profile and track down a serial killer. The film is set to be directed by Damián Szifron. Woodley will serve as a producer on the film. She joined Shia Lebeouf and Robert De Niro in the upcoming crime drama After Exile, with Joshua Michael Stern as director.  She is attached to star in animated feature Arkie and romance film No Baggage, which are in pre-production and development respectively.
Shailene Woodley