Star Trek’s Klingons stopped using a particular espionage tactic against the United Federation of Planets afterStar Trek VI: The Undiscovered Country. Set in 2293,Star Trek VIushered in a détente between the Klingon Empire and the Federation after the Klingon moon Praxis exploded. With the Empire on the brink of economic collapse, Klingon Chancellor Gorkon (David Warner) sued for peace with the Federation.Peace was ultimately achieved and lasted well into the 24th centuryStar Trek: The Next Generationera.
At the height of the 23rd century Cold War between the Klingon Empire and the Federation - which escalated to violence in theKlingon War of 2256-2257 as seen inStar Trek: Discovery- the Klingons developed the means to surgically alter themselves to appear human. Given the stark physiological differences between Klingons and humans, this was a brutal and painful procedure, butat least two known Klingons were subjected to the torture in order to spy on Starfleet and the Federation. However, this practice stopped afterStar Trek VI.

Why Klingons Stopped Infiltrating The Federation Disguised As Humans After Star Trek VI
Peace Ended One Particular Klingon Spy Practice
AfterStar Trek VI: The Undiscovered Countrymarked a new era of cooperation between the Federation and Klingon Empire, there was no longer any reason for Klingons to surgically alter themselves into humans to become spies.The Klingons became allies of the Federation and openly worked with Starfleet. Lieutenant Worf (Michael Dorn) then became thefirst Klingon in Starfleet, rising to become Security Chief of the USS Enterprise-D inStar Trek: The Next Generation.
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The Klingons are one of the most diverse alien species in all of Star Trek, and multiple different variations have appeared in canon from TOS onward.
While it’s unknown how many Klingons became human spies in the 23rd century, the procedure depicted inStar Trek: Discoveryis so torturous that it’s likely few Klingon warriors subjected themselves to it. Culturally, Klingons pride themselves on facing enemies in glorious battle, and honorable deaths are seen as a gateway toSto-vo-kor(Klingon heaven).Besides the indignity of being turned into a human, the process is also apparently irreversible, and this is understandably not welcomed by the Klingons.

Star Trek Has 2 Famous Klingons Disguised As Humans
Star Trek: Discovery, TOS & DS9 Introduced Two Klingon Spies
Star Trek’s most infamous Klingon-turned-human is Arne Darvin (Charlie Brill). InStar Trek: The Original Series' classic episode, “The Trouble With Tribbles,” Darvin was a Klingon Intelligence operative who was installed as the aide to Federation Undersecretary Nilz Baris (William Schallert). Thanks toCaptain James T. Kirk(William Shatner) and crew of the USS Enterprise,Darvin’s mission to poison the quadrotriticale grain vital for Sherman’s Planetfailed when a Tribble exposed Arne as a Klingon.
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In the 24th century ofStar Trek: Deep Space Nine,Arne Darvin returned and attempted to take revenge on Captain Kirk. Darvin used a Bajoran Orb of Time to travel back to the 23rd century and assassinate Kirk with abomb he placed inside a Tribble. However, thanks to Captain Benjamin Sisko (Avery Brooks) and the crew of Deep Space Nine, Darvin failed once again and was apprehended.
At the end of Star Trek: Discovery season 2, Starfleet assigned Ash Tyler command of Section 31.
Star Trek: Discoverynot only depicted the gruesome procedure to surgically alter a Klingon into a human, but also introduced its first victim: Voq (Shazad Latif).Voq was physically transformed into a human with the likeness of Starfleet Lieutenant Ash Tyler. Voq/Ash became part of the USS Discovery’s crew, but he later joined his love, L’Rell (Mary Chieffo), when she became Chancellor of the Klingon Empire. At theend ofStar Trek: Discoveryseason 2, Starfleet assigned Ash Tyler command of Section 31.

Romulans Infiltrated The Federation Disguised As Vulcans - And Did A Lot More Damage
Commodore Oh Altered The Course Of The Federation
Like the Klingons, the Romulans also used moles to infiltrate Starfleet, but they were able to do significantly more damage and even altered the course of the Federation in the late 24th century.Star Trek: Picardseason 1 revealed thatthe Romulan Tal Shiar sect called the Zhat Vash installed General Nedar (Tamlyn Tomita) as Commodore Oh, who rose to become Starfleet’s Head of Security. Oh was aided by Narissa (Peyton List), who performed black ops as assassinations for Starfleet Intelligence as Lieutenant Rizzo.
Why Star Trek’s Klingons & Romulans Both Have Bird-Of-Prey Starships
The surprising production reason & the clever in-universe explanation for Star Trek’s Klingons & Romulans both having starships called Bird-of-Prey.
Commodore Oh posed as a Vulcan, which was far simpler than Klingons being altered into humans, since Romulans are a genetic offshoot of the Vulcan species. Similarly, Narissa could easily become the human Lt. Rizzo with a few minor physical alterations, like rounding out her pointed ears. Captain Kirk inStar Trek: The Original SeriesandCounselor Deanna Troi (Marina Sirtis) becoming a RomulaninStar Trek: The Next Generationshow how relatively easy and painless back-and-forth transformation is.

Star Trek: Strange New Worldsrevealed Nurse Christine Chapel (Jess Bush) helped develop Starfleet’s technology to surgically alter humans into alien species.
The damage Commodore Oh secretly inflicted on the Federation was catastrophic. Oh engineered the synthetic workers of Mars going rogue.Star Trek: Picard’s Mars Attack of 2385killed 92,000 souls and destroyed the Federation fleet under construction to save the Romulan people from their sun going supernova, withOh’s goal of the Federation banning all artificial life forms lasting for nearly 15 years. By infiltrating Starfleet as a Vulcan and humans, Commodore Oh and her Romulan followers were much more effective than Klingons disguised as humans ever were inStar Trek.