September 21 2021 — Ana Belén Montes (born February 28, 1957) is a former American senior analyst at the Defense Intelligence Agency in the United States and convicted spy. On September 21, 2001, she was arrested and subsequently charged with conspiracy to commit espionage for the government of Cuba. Montes eventually pleaded guilty to spying and in October 2002, was sentenced to a 25-year prison term followed by five years’ probation. Montes is incarcerated at FMC Carswell in Fort Worth, Texas. Her tentative release date is listed as July 1, 2023. Follow us on Twitter: @INTEL_TODAY
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UPDATE (January 9 2023) — Ana Montes, 65, was released from prison last Friday. She was granted early release from federal prison in Fort Worth, largely on account of good behavior.
“I obeyed my conscience rather than the law,” Montes told the judge who sentenced her in 2002 to 25 years in prison following her conviction for conspiracy to commit espionage.
U.S. District Judge Ricardo M. Urbina ruled in 2002 that upon her release, Montes should be placed under supervision for five years, during which time her internet and computer usage would be monitored and unpermitted contact with foreign governments forbidden. Any conditions attached to her release Friday were not immediately clear. [Washington Post]
END of UPDATE
Ana Montes appeared to be a model employee of the Defense Intelligence Agency (DIA), advancing quickly through the ranks to become its top analyst on Cuban affairs.
But for sixteen years Montes sent Castro some of America’s most closely guarded secrets and at the same time influenced what the United States thought it knew about Cuba.
Ana Montes is the only member of the U.S. intelligence community ever convicted of espionage for the Cuban government. Yet her arrest, ten days after 9/11, went largely unnoticed.
Scott W. Carmichael, the DIA investigator who pursued the Montes case from initial suspicion to arrest, has now written the first account of the Ana Montes story from within the government.
True Believer: Inside the Investigation and Capture of Ana Montes, Cuba’s Master Spy (Naval Institute Press, Annapolis, 2007, 179 pages) puts the reader inside the disquieted mind of the professional counterintelligence officer, someone paid to suspect the worst about his colleagues. [“True Believer” Leaves Many Questions Unanswered]
Carmichael examined Montes’ desk one night during the investigation and found that it matched her taciturn personality.
It was orderly and devoid of personal items with the exception of a Shakespeare couplet [Henry V – ACT II · SCENE II] written in script and pinned to the wall:
“The king hath note of all that they intend,
by interceptions which they dream not of.”
These words are engraved on a plaque at Bletchley Park, the manor house near London that housed British signals intelligence and code-breaking during World War II.
The Case of the Cuban spy
The following is the official story of Ana Montes according to the FBI.
Just 10 days after the attacks of 9/11, the FBI arrested a 44-year-old woman named Ana Belen Montes.
She had nothing to do with the terrorist strikes, but her arrest had everything to do with protecting the country at a time when national security was of paramount importance.
Montes, it turned out, was spying for the Cubans from inside the U.S. intelligence community itself—as a senior analyst with the Defense Intelligence Agency, or DIA.
And she was soon to have access to classified information about America’s planned invasion of Afghanistan the following month.
Montes was actually the DIA’s top Cuban analyst and was known throughout the U.S. intelligence community for her expertise.
Little did anyone know how much of an expert she had become…and how much she was leaking classified U.S. military information and deliberately distorting the government’s views on Cuba.
It began as a classic tale of recruitment. In 1984, Montes held a clerical job at the Department of Justice in Washington. She often spoke openly against the U.S. government’s policies towards Central America.
Soon, her opinions caught the attention of Cuban “officials” who thought she’d be sympathetic to their cause. She met with them. Soon after, Montes agreed to help Cuba.
She knew she needed a job inside the intelligence community to do that, so she applied at DIA, a key producer of intelligence for the Pentagon. By the time she started work there in 1985, she was a fully recruited spy.
Montes was smart. To escape detection, she never removed any documents from work, electronically or in hard copy. Instead, she kept the details in her head and went home and typed them up on her laptop.
Then, she transferred the information onto encrypted disks. After receiving instructions from the Cubans in code via short-wave radio, she’d meet with her handler and turn over the disks.
During her years at DIA, security officials learned about her foreign policy views and were concerned about her access to sensitive information, but they had no reason to believe she was sharing secrets. And she had passed a polygraph.
Her downfall began in 1996, when an astute DIA colleague—acting on a gut feeling—reported to a security official that he felt Montes might be under the influence of Cuban intelligence. The official interviewed her, but she admitted nothing.
The security officer filed the interview away until four years later, when he learned that the FBI was working to uncover an unidentified Cuban agent operating in Washington. He contacted the Bureau with his suspicions. After a careful review of the facts, the FBI opened an investigation.
Through physical and electronic surveillance and covert searches, the FBI was able to build a case against Montes. Agents also wanted to identify her Cuban handler and were waiting for a face-to-face meeting between the two of them, which is why they held off arresting her for some time.
However, outside events overtook the investigation—as a result of the 9/11 attacks, Montes was about to be assigned work related to U.S. war plans. The Bureau and DIA didn’t want that to happen, so she was arrested.
What was Montes’ motivation for spying? Pure ideology—she disagreed with U.S. foreign policy. Montes accepted no money for passing classified information, except for reimbursements for some expenses.
Montes, who acknowledged revealing the identities of four American undercover intelligence officers working in Cuba, pled guilty in 2002 and was sentenced to 25 years in prison. [FBI]
Montes communicated with the Cuban Intelligence Service through encrypted messages and received her instructions through shortwave encrypted transmissions from Cuba.
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In addition, Montes communicated by coded numeric pager messages with the Cuban Intelligence Service by public telephones located in the District of Columbia and Maryland. [US Federal prosecutors]
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COMMENT: A new version of a computer-based cyber-security training course from the Pentagon is available online.
Despite evidence to the contrary, the Pentagon still classifies disillusionment with U.S. foreign policy as a “threat indicator” that a federal employee might be a spy.
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Ana Montes did much harm spying for Cuba. Chances are, you haven’t heard of her. — WP Jim Popkin (April 13 2013)
Two double agents, a prison swap and the code from outer space: did this spy-v-spy duel save US-Cuban relations? — Guardian Jim Popkin (December 22 2014)
Pentagon Training Still Says Dissent Is A Threat ‘Indicator’
Declassified: Untold Stories of American Spies Season 1, Episode 4 Cuba: Traitor On Inside
“True Believer” Leaves Many Questions Unanswered — CubaNews
The most dangerous U.S. spy you’ve never heard of — CNN
The Queen of Cuba: The two stories of Ana Montes
On This Day — Ana Montes Is Arrested (September 21 2001)
On This Day — Ana Montes Is Arrested (September 21 2001) 
20 Years Ago — Ana Montes Is Arrested (September 21 2001) [UPDATE : Montes released from prison]