It was the early hours of New Year's Day when Ana Walshe reportedly left her home in Massachusetts to catch a flight.
The mother-of-three, who originally had a flight booked for January 3, had a work emergency and needed to fly to Washington earlier, her husband Brian told police.
That morning, she "got ready" and "kissed" Brian goodbye, before telling him "to go back to sleep", a criminal affidavit states, according to CNN.
Ana, who was last seen by a family member between 4am and 5am, then reportedly used a rideshare service to travel to Logan Airport, police were told.
However, according to police, the real estate executive never boarded the plane and hasn't been seen since.
Three days later, Ana, who has three young sons aged from two to six years old, was reported missing by her husband and employer.
Watch: Cohasset Police Chief William Quigley addresses media.
Police have since launched an investigation into the missing 39-year-old, whose credit and debit cards haven't been active since January 1.
"[Her] cell phone has been off since the first of the year," said Cohasset Police Chief William Quigley.
Police have also not been able to confirm that she took a ride share that morning, said Quigley.
A friend of Ana's, Alissa Kirby, told WCVB, "Honestly, I’m scared. Really, really scared."