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Raktajino wasn't known in Federation facilities such as Deep Space Station K-7 until sometime after 2268, as the time traveling Odo, while existing as a Solid, attempted to order one at that facility, only to be told by a waitress that it was not available – and that another patron, who planned to return later, had asked for it as well. Soon afterward, numerous Klingons from the IKS Gr'oth, taking shore leave on the station, requested the drink, much to the waitress' annoyance. She later warned that Odo's companions (Worf, Doctor Bashir, and Chief O'Brien) not dare ask for it; her explanation of why they shouldn't request it came as such a surprise to the table's occupants (three of whom didn't see any Klingons — and the one who did had absolutely no intention of identifying them as such) that she assumed they were intoxicated and refused to serve them. (DS9: "Trials and Tribble-ations")
Jadzia Dax and Julian Bashir drank raktajino occasionally. In 2369 they were sitting at the Replimat and performing repairs during the absence of Chief O'Brien. Bashir asked Dax if she would like to have another one but Dax said that this would keep her up all night. Bashir then answered he knew better things to keep her up all night than Klingon coffee. Later that year Dax and Bashir ordered two raktajinos, extra strong. In 2370 Bashir said, again in a flirtatious manner, "Your replicator or mine" in response to Jadzia's suggestion that they have a raktajino together. (DS9: "Dax", "If Wishes Were Horses", "The Alternate")
Benjamin Sisko started every morning off with a raktajino; in fact, he was not awake, much less did he talk to anyone until he had his first cup. Sisko also enjoyed drinking his raktajino with jacarine peel; this drink also went well with icoberry torte. During 2373, however, Benjamin was trying to cut back on his consumption of raktajino. (DS9: "Second Sight", "The Homecoming", "Children of Time")
In 2371, Sisko told a nurse on Trill to tell Doctor Torvin to get himself a raktajino – as opposed to preparing a new host for the Dax symbiont – just before confronting Doctor Renhol. (DS9: "Equilibrium")
Soon after, Gul Dukat sarcastically commented that he hoped Sisko hadn't been killed while ordering a raktajino, after a counter-insurgency program had replicated a disruptor that was firing at Ops personnel. (DS9: "Civil Defense")
Jake himself enjoyed his raktajino extra sweet, and drank it with makapa bread, which when dipped in the raktajino would induce it to froth up with a peppermint-flavored foam. This was, apparently, not a very common pairing, as Benjamin, a dedicated raktajino drinker, was surprised the first time he witnessed it. (DS9: "For the Cause")
At the request of Chief O'Brien, Quark tried to create a decaffeinated version of raktajino in 2373. This was for the benefit of Major Kira, who was pregnant with O'Brien's son at the time. Quarktajino, as Odo called it, was apparently disgusting. (DS9: "Nor the Battle to the Strong")