Four postal workers transform themselves into a team of detectives to track down intended recipients of undeliverable mail. Their missions take them out of the office and into an unpredictable world where redirected letters and packages can save lives, solve crimes, reunite old loves and change futures by arriving late but somehow always on time.
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Oliver leads the postal detective team in investigating a letter from a ten-year-old boy alerting his grandmother he's running away after they've been mysteriously separated. Meanwhile, the rest of the Dead Letter Office team are preparing for the arrival of a new supervisor, the larger-than-life Theresa Capodiamonte, who challenges them to take greater risks to deliver the seemingly undeliverable letters and packages.
The team retrieve a mangled letter addressed "To Whom It May Concern." Their investigation hits a road block with an old postmark and a government form for the U.S. Army Office. The accompanying letter from a young woman describes her search for a soldier who saved her life and helped her escape Afghanistan during the war. When they discover the Army officer has gone off the grid, Supervisor Theresa Capodiamonte challenges them to find the intended recipient, even if he doesn't want to be found.
When the team discover an undelivered love letter, their initial investigation unravels more questions than answers. As their new Supervisor implements stricter policies and procedures, the team's challenges are multiplied. In the letter, ranch owner Sam has written his childhood sweetheart with a passionate plea. But the Postables recognize a domino effect this long lost letter will have on its recipient and the people in her life. Unsure of how to proceed, the team regroups and comes to learn that there is a right time for everything in life... even love.
The past catches up with the postal detectives when Oliver leads Shane, Rita, and Norman on the investigation of a package from a son to his estranged father. The team leaves their strict supervisor Cora behind as they race against time to track down the father before it's too late. But when Shane stumbles onto a clue that decodes the package's true meaning, the Postables discover a tragedy that changes everything. Meanwhile, Cora has a surprising change of heart that inspires the team.
The Dead Letter Office detectives are dealt their most heart-wrenching challenge yet when they receive an unusual package with a letter from a deceased woman. The team help the woman's two daughters on a dramatic journey to piece together clues from the past, so that each can move towards a better future.
When the postal detectives discover a letter postmarked with a future date, it sets off a chain reaction that leads them down a surprising, emotional journey. As Rita prepares for the Miss Special Delivery pageant, and faces threats from Glynis Rucker, an intimidating supervisor whose daughter is also competing for the crown, Oliver, Shane and Norman find themselves in the middle of a unique couple's struggle for acceptance.
Oliver, Shane, Rita and Norman track down a talented but anonymous singer/songwriter using only the lyrics of his undiscovered song, taking on an investigation like no other. As the team follows the song's clues, they quickly unravel the details of a fateful night, where two lives were forever changed.
An old friend of Shane's, visiting supervisor Rebecca Starkwell, gives special approval to the postal detectives to intervene when one man receives devastating news that could lead him to make an irreversible mistake. On a mission to stop him, the postal workers' investigation leads them to another stunning revelation that quickly becomes a matter of life or death.