You know that game where you keep translating a sentence back and forth between two languages, until the original statement is only a vage memory? It also works with transcription between alphabets. I just came across a real-life example.
In 1991, Franz Viehböck was Austria’s first Raumfahrer (astronaut or, in this case, cosmonaut). A correct name tag was stuck on his clothing, along with a Cyrillic version: Фибёк. That’s not a bad approximation of the original pronunciation,
/ˈfiːbœk/, and probably based on official rules for German-to-Russian transcription.
Name tag, on display at the House of Austrian History in Vienna.
After his flight, Viehböck got an official certificate, or rather two: one in Russian, one in English. But while the former once again spells his name as фибёк, the latter displays an entirely new version of his name: Feeberk.
That makes /ˈfiːbɜːk/ in IPA, which is pretty close to the German original if you ask me. But why didn’t the aerospace authorities check how their employee’s name was spelt? Didn’t they have a photocopy of his passport? Didn’t they have a name tag left? Was there no radio contact? Did they do it on purpose because they were fed up with him? Was it an in-joke?
None of the above perhaps. This happened in the autumn of 1991. The Baltic republics had just broken away from the USSR, the Ukraine was to follow within weeks. The Union was not going to see the end of the year. All was turmoil.
Under the circumstances, issues of transcription may have taken a backseat, if not an ejection seat. Фибёк, Шмибёк – Feeberk, Shmeeberk.
Certificate, on display in the same museum.
Gaston Dorren, language writer 
Transcription… The Soviet Union was using the French transcription in passports, the Russian Federation opted for English: Iouri Gagarine suddenly became Yury (or Yuriy) Gagarin, but nothing changed in the Russian original, of course (Юрий Гагарин).
Belarus and Ukraine have legally modified the Cyrillic original in accordance with their official languages: Надежда became Надзея, Дмитрий became Дмитро and on top of that they applied transcription. Thus, a Soviet Nikolai became Nikolay in Russia, Nikalay in Belarus and Mykola in Ukraine.
In the early years of independence the rules of transcription were unstable: a Ukrainian guy with the last name Щит (“shield” in Ukrainian and Russian) was first transcribed as Chtchit, then simply Shit (a photo is hanging around on the web), now he must be Shchyt or so.
Russian driving license applies a system different from the Russian passports (ь is omitted in the passports, but automatically appears as an apostrophe in the driving license), and Russian banks transliterate the name on the credit card according to their rules, so a Russian guy who rents a car abroad can perfectly show three “different” documents.
Indeed, Cyrillic to Latin is a complete mess (poor cosmonought), but Latin/AnythingElse to Cyrillic works perfectly. All proper nouns are in most cases phonetically transcribed into Russian, so if you don’t know how to pronounce Hughes, Hainaut, Hammarskjöld, Pécs, Wałęsa or Brzęczyszczykiewicz (https://youtu.be/t-fcrn1Edik) just find the Russian version of the corresponding Wikipedia page and read the name aloud. You’ve got it.
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