Deany Ray Books in Order: Piper Harris, Charlie Cooper, Hailey Webb, and Ouna Bay Mysteries
Deany Ray writes lighthearted cozy mysteries built around amateur sleuths, small-town settings, recurring friendships, family relationships, and plenty of trouble. Her books range from the Florida-set Piper Harris mysteries to the California-based Hailey Webb stories and the small-town worlds of Charlie Cooper and Ouna Bay.
The easiest way to read Deany Ray is series by series. Each series has its own protagonist and storyline, and the individual books are best read in numbered order. That is particularly useful for readers who want the character relationships and ongoing personal stories to develop naturally.
Piper Harris Mysteries in Order
The Piper Harris Mysteries are currently Deany Ray’s longest and most active series. Piper and her grandmother relocate to Bitter End, Florida, through witness protection after their involvement with a motorcycle gang creates serious problems. The official series description sets up the combination of crime, family complications, Florida small-town life, and humor that drives the books.
There are seven released novels, with an eighth book, Dead Ringer, scheduled for April 2027.
1. Coming in Hot
Coming in Hot introduces Piper Harris and her grandmother after they enter witness protection and leave Oregon for Bitter End, Florida. Their new life is supposed to keep them safe from the biker gang they betrayed, but settling into a quiet Florida existence proves much harder than expected.
The novel establishes Piper’s new surroundings, the people around her, and the unusual combination of witness protection and cozy-mystery chaos that defines the series.
2. Fool Me Once
Piper’s new life in Bitter End continues to produce unexpected complications. As she becomes more familiar with the town and the people around her, another mystery gives her plenty of reasons to become involved in matters that would probably be safer left alone.
3. Bar None
Two months after Piper and her grandmother arrive in Bitter End, life has improved only slightly. Another murder gives Piper a new mystery to investigate, bringing more trouble into the witness-protection life she was hoping would finally become ordinary.
4. Closed Casket
Piper faces another murder investigation as life in Bitter End continues to be anything but peaceful. The fourth book keeps the series’ combination of cozy mystery, recurring characters, humor, and Piper’s unusual background moving forward.
5. Hole in One
Piper’s latest mystery takes her into another investigation where the seemingly ordinary world of Bitter End once again hides something much darker. The fifth book continues the character relationships and ongoing story established in the first four novels.
6. Be My Valentine
Valentine’s Day provides the setting for another Piper Harris mystery. Romance and celebration do little to keep Piper away from trouble, and the sixth installment continues the series’ blend of murder, humor, and small-town complications.
7. Bad Company
Bad Company is the seventh Piper Harris Mystery and the latest released novel in the series. It continues Piper’s adventures in Bitter End while adding another case to the increasingly complicated life she has built in Florida.
It was released in July 2025.
8. Dead Ringer
Dead Ringer is the upcoming eighth Piper Harris Mystery. It is currently listed for publication on April 13, 2027. Because it has not yet been released, it should be treated as an upcoming installment rather than part of the currently available reading sequence.
Charlie Cooper Mysteries in Order
The Charlie Cooper Mysteries follow Charlie, an undercover investigator who returns to her quirky hometown as part of a major drug investigation. Her assignment becomes complicated when she encounters murder, eccentric relatives, nosy locals, and two women, Marge and Celeste, who become her crime-solving partners.
The series contains eight numbered mysteries plus Jingled, a Christmas short story.
1. Jammed
Jammed introduces Charlie Cooper and her undercover assignment in her hometown. What should be a straightforward investigation becomes much more complicated once dead bodies begin appearing and Charlie discovers that her family and the town’s residents may make staying undercover considerably harder.
The novel establishes the cast and comic crime-solving tone that carries through the series.
2. Pickled
Charlie continues working undercover while another mystery gives her yet another reason to become involved in the town’s criminal problems. Her relationships with Marge, Celeste, and the local detective continue to develop.
3. Diced
Another murder puts Charlie’s investigative skills to work. The third book expands the world established in the first two mysteries while continuing the combination of undercover work, friendship, romance, and cozy-mystery humor.
4. Glazed
Charlie finds herself involved in another case where the seemingly ordinary life of her hometown conceals a much more complicated mystery. Her undercover assignment remains an important part of the larger storyline.
5. Dazzled
The fifth Charlie Cooper mystery brings another murder investigation and another opportunity for Charlie to get herself into trouble while trying to solve a case.
6. Berried
Charlie returns for another small-town mystery involving suspicious circumstances, familiar characters, and the continuing complications of her undercover role.
7. Juiced
The seventh novel continues Charlie’s adventures and her partnership with Marge and Celeste as another case disrupts life in her hometown.
8. Truffled
Truffled is the eighth numbered Charlie Cooper Mystery. It continues Charlie’s ongoing story and the series’ mix of mystery, humor, family, and small-town complications.
The first eight numbered books run from Jammed through Truffled.
Jingled
Jingled is a Charlie Cooper Christmas short story, not a ninth full-length novel. Charlie’s Christmas Eve takes an unexpected turn when a seemingly perfect family celebration is disrupted by ruined food, a damaged Christmas tree, and someone holding her at gunpoint.
Because it is explicitly described by the author as a holiday short story, readers can treat it as an optional companion to the eight main Charlie Cooper mysteries.
Hailey Webb Mysteries in Order
The Hailey Webb Mysteries move the action to Palm Shores, California. Hailey Webb, a 28-year-old assistant and errand runner for the local newspaper, keeps stumbling into murder cases despite having plenty of other responsibilities.
There are five books in the series.
1. Hot Off the Press
Hailey Webb starts over after major changes in her personal life and takes a job as an assistant and errand runner for the local newspaper in Palm Shores. Her first day becomes considerably more interesting when she discovers a dead treasure hunter on a boat.
Instead of simply being the newspaper’s assistant, Hailey quickly finds herself pulled into a murder investigation while dealing with parts of her own past that she would rather forget.
2. Act it Out
Hailey continues working for the local newspaper while finding herself involved in another mystery. Her everyday errands once again become entangled with murder, giving her another reason to investigate rather than simply delivering newspapers and running errands.
3. Off Target
Hailey enjoys a night out with her best friend Kat when an evening at their favorite bar turns into another mystery. The third book continues the series’ mixture of friendship, romance, humor, and murder investigation.
4. Dead Man’s Float
Hailey takes on another responsibility when she house-sits, but the job comes with an unexpected problem: someone dies. What should have been a simple favor becomes another case for Hailey to investigate.
5. Pretty Dead
Hailey is still working as an assistant for the Palm Shores Gazette when another mystery lands in her path. The fifth book brings the current Hailey Webb series to its latest published installment.
Ouna Bay Cozy Mysteries in Order
The Ouna Bay Cozy Mysteries are Deany Ray’s earliest series. The stories center on Becky, owner of the Blue Bay Café, and her best friend Rosalie. Together, they find themselves investigating crimes involving suspicious deaths, sabotage, local businesses, and the residents of Ouna Bay.
There are four books in the series.
1. A Sweet Chunk of Madness
Becky’s Blue Bay Café is thriving until someone starts trying to interfere with the business. As suspicious events begin piling up, Becky and her best friend Rosalie decide that waiting for someone else to solve the problem is not an option.
The first book introduces Ouna Bay, the Blue Bay Café, Becky, Rosalie, Houston, and Gerry the dog.
2. Vanilla Bean Murder
Rosalie is excited to begin working at Becky’s café, but her first day takes a terrible turn when she discovers the body of a bank director. Suddenly, Rosalie becomes a person of interest in a murder investigation, leaving Becky and Rosalie with another mystery to solve.
3. Cake Contest Murder
The annual Ouna Bay town fair and cake contest should be a cheerful community event, but everything changes when one of the town’s most disliked residents dies in the middle of the competition.
Becky and Rosalie once again find themselves investigating a murder while trying to restore some sense of normality to the café and the town.
4. Peanut Butter Crumble Murder
A celebration at the local country club turns into another murder investigation when a guest of honor is found dead after eating one of Becky’s famous peanut butter crumble cupcakes. With the evidence pointing toward her café, Becky has to figure out who used her cupcake to frame her and why.
Deany Ray Books by Publication Order
Readers looking for every Deany Ray book in chronological publication order should know that the series overlap in time, so a series-by-series order is generally much easier to follow.
The earliest series is Ouna Bay, beginning with A Sweet Chunk of Madness in 2015. Charlie Cooper followed in 2016, Hailey Webb in 2020, and Piper Harris in 2023.
A simplified series timeline is:
- Ouna Bay Cozy Mysteries: 2015–2016
- Charlie Cooper Mysteries: 2016–2022
- Hailey Webb Mysteries: 2020–2023
- Piper Harris Mysteries: 2023–present
This timeline is more useful than attempting to mix all the individual books into one master list because the series have separate protagonists and settings.
Which Deany Ray Series Should You Start With?
Start With Piper Harris for Ray’s Current Series
If you want to follow Deany Ray’s most current series, begin with Coming in Hot. Piper’s unusual witness-protection background gives the series a different setup from the author’s other cozy mysteries. The series is also still active, with Dead Ringer scheduled for 2027.
Start With Charlie Cooper for an Undercover Mystery
Jammed is the right starting point if the idea of an undercover protagonist returning to her eccentric hometown appeals to you. The series has eight numbered mysteries, giving readers a substantial completed sequence to work through.
Start With Hailey Webb for a Newspaper Sleuth
Hot Off the Press introduces Hailey Webb and her accidental crime-solving career at the Palm Shores newspaper. The five-book series is complete as currently published.
Start With Ouna Bay for a Small-Town Café Mystery
A Sweet Chunk of Madness is the natural choice if you prefer cozy mysteries centered on a café, friendships, local gossip, and community life. It also happens to be Deany Ray’s first published book.
Do Deany Ray’s Series Connect?
Deany Ray’s four main mystery series are best treated as separate series rather than one continuous reading universe. Each has its own protagonist, setting, and central supporting cast.
The author organizes them separately on her store, with dedicated collections for Piper Harris, Charlie Cooper, Ouna Bay, and Hailey Webb.
That means you do not need to read Ouna Bay before starting Piper Harris, for example. Readers can choose a series based on the protagonist and setting they find most appealing.
How Many Deany Ray Books Are There?
There are currently 26 numbered books across Deany Ray’s four main mystery series: four Ouna Bay books, nine Charlie Cooper works including Jingled, five Hailey Webb mysteries, and eight Piper Harris books when the upcoming Dead Ringer is included. However, Jingled is a short story rather than a full-length novel, and Dead Ringer has not yet been released.
For currently released full-length books, the count is lower because Dead Ringer is still forthcoming and Jingled is a short story.
About Deany Ray
Deany Ray is a cozy mystery author who was born and raised in Romania and later moved to Germany, where she lives in Cologne. According to her author biography, she has long enjoyed reading cozy mysteries and decided to write the kind of entertaining mystery stories she enjoys herself.
Her bibliography reflects that preference: the books consistently combine murder investigations with humor, friendships, family relationships, everyday settings, and amateur sleuths who have a habit of finding themselves much closer to danger than they intended.
Frequently Asked Questions
What is the first Deany Ray book?
A Sweet Chunk of Madness is Deany Ray’s first published book and the first Ouna Bay Cozy Mystery. It was published in 2015.
What is the first Piper Harris book?
Coming in Hot is the first Piper Harris Mystery. It introduces Piper and her grandmother as they enter witness protection and relocate to Bitter End, Florida.
How many Piper Harris books are there?
There are seven released Piper Harris novels through Bad Company. Dead Ringer is Book 8 and is currently scheduled for April 13, 2027.
How many Charlie Cooper books are there?
The Charlie Cooper series has eight numbered mysteries, from Jammed through Truffled. Jingled is an additional Christmas short story featuring Charlie.
How many Hailey Webb books are there?
There are five Hailey Webb Mysteries: Hot Off the Press, Act it Out, Off Target, Dead Man’s Float, and Pretty Dead.
How many Ouna Bay books are there?
The Ouna Bay Cozy Mysteries consist of four books: A Sweet Chunk of Madness, Vanilla Bean Murder, Cake Contest Murder, and Peanut Butter Crumble Murder.
Can I read Deany Ray’s series out of order?
Yes, you can start any of the four series independently. Within a particular series, however, reading from Book 1 onward is preferable because the protagonists, relationships, and supporting characters continue across the books.
Is Deany Ray still writing Piper Harris books?
Yes. Bad Company was the latest released Piper Harris mystery as of 2025, and Dead Ringer, Book 8, is currently scheduled for April 2027.
Final Thoughts
Deany Ray’s books are a good example of a mystery author’s bibliography where series-by-series reading is much more useful than one giant publication list. The four main series each offer a different setup: Piper Harris brings witness protection and Florida crime, Charlie Cooper combines undercover work with small-town chaos, Hailey Webb solves crimes around a California newspaper, and Ouna Bay revolves around a café, friendship, and community life.
For the newest ongoing series, start with Coming in Hot. For Ray’s complete earliest series, start with A Sweet Chunk of Madness. Whichever series you choose, reading the books in their numbered order will give you the clearest progression of each sleuth’s story.
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