Warning: SPOILERS for the Short Trek episode "Ask Not".
Star Trek revealed the origin of Starfleet's test of character, a scenario that would evolve into the infamous Kobayashi Maru no-win scenario. As the Star Trek franchise continues to expand on CBS All-Access, Short Treks serve to bridge the gap for fans eager for the debut of Star Trek: Picard and the return of Star Trek: Discovery in 2020. Even better, the Short Treks are also a chance to spend more time with Captain Christopher Pike (Anson Mount), Number One (Rebecca Romijn), and Spock (Ethan Peck), who have been centerpiece characters in this season's crop of mini-episodes. Intriguingly, the newest short, "Ask Not", features a test very similar to the Kobayashi Maru.
Introduced in Star Trek II: The Wrath of Khan, the Kobayashi Maru was used by Admiral Kirk (William Shatner) and Captain Spock (Leonard Nimoy) to assess the command capabilities of Lieutenant Saavik (Kirstie Alley). In the no-win scenario, the cadet would simulate commanding a starship that encounters the Kobayashi Maru, a civilian freighter under attack by Klingons in the Neutral Zone. There's no way to actually triumph in the simulation as it's impossible to rescue the civilians, avoid conflict with the Klingons, and escape the Neutral Zone in one piece, but the choices the test-taker makes reveals their character and what kind of commander they would be. Infamously, Kirk was the only cadet who ever beat the Kobayashi Maru - by cheating; he reprogrammed the simulation so that he could win. ("It had the virtue of never having been tried," was Kirk's justification.) Starfleet agreed and gave Kirk a commendation for 'original thinking'.
"Ask Not" revealed that similar tests of character were common in Starfleet during The Original Series' era and Captain Pike used it on an unwitting cadet named Thira Sidhu (Amrit Kaur). While Sidhu waited on a Starbase for her transfer to the Starship Enterprise, Pike is brought to her as a prisoner who has been stripped of his rank. Sidhu is ordered to watch Kirk at gunpoint while the Starbase and the Enterprise fight off an attack by the Tholians. Befuddled but trying to follow these drastic orders, Sidhu has to contend with Pike trying to assert his command over her. As they argue about protocol and loopholes to Starfleet regulations, Pike insists on Sidhu allowing him to join the fight against the Tholians and he even resorts to emotional blackmail before attempting escape. Resolute despite her no-win scenario, Sidhu threatens to shoot Pike with a phaser if he refuses to stand down, at which point, a satisfied Pike drops the pretense and reveals it was all an intense simulation designed to test Sidhu's character - and the cadet passed with flying colors. Her reward was being personally escorted aboard the Enterprise by Captain Pike, meeting Number One and Spock, and beginning her duty in Engineering.
It turns out the elaborate ruse designed to test a cadet's character was the brainchild of Number One, and Spock added that he's learned to expect "no mercy" from the Enterprise's First Officer. It seems Number One's tests of character became widely adopted throughout Starfleet. Amusingly, Cadet Sidhu believed the scenario because she naturally assumed someone like Captain Pike would be "too busy" to partake in such a ruse. After all, Sidhu is just a cadet transferring to Engineering, not someone on the Command track to be a Captain - why go through the trouble of staging such a tortuous trial for a midshipman? But perhaps Pike has greater plans for Cadet Sidhu aboard the Enterprise and this was the first step towards her greater destiny.
Similar tests of character were also used in later Star Trek series: In the Star Trek: The Next Generation episode "Thine Own Self", Counselor Deanna Troi (Marina Sirtis) faced a similar no-win scenario during her Bridge Officer's Test and she even noted its similarities to the Kobayashi Maru. The Star Trek: Voyager episode "Learning Curve" substituted a Ferengi ship and Romulan Warbirds in its holodeck training scenario, though Lieutenant Tuvok (Tim Russ) noted the correct solution was to retreat. Finally, in Star Trek 2009's Kelvin alternate reality, Kirk (Chris Pine) arrogantly cheated to beat the Kobayashi Maru scenario, infuriating Spock (Zachary Quinto), who programmed the test.