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I can look up the etymology for indubitably... but how did a word like this, which pretty much exactly parallels "undoubtedly," come into use? This might be an unanswerable question, but how did two words with such parallel meanings, the only nuance distinguishing them being that you sound more pretentious if you say "indubitably", come to coexist?

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All I know is that when I translate people from English to German, I am really astonished on how many adverbs and adjectives especially there are in English that have almost exactly the same meaning. And it seems to be an attribute of speeches and sermons in English to describe something with 2-3 attributes to stake out the field. I usually do not find the same wealth of adjectives or adverbs and end up translating only 1-2. I would guess therefore that it is an inner urge of the English community to have alternatives and almost synonyms for their style of expression. –  malach Oct 30 '10 at 6:31
This actually reminds me of the "expectorate" vs "spit" question. By which I mean to say that there are lots and lots of words that have "more pretentious" synonyms. This particular case is surely interesting in that the synonyms look so much alike and ultimately come from the same Latin word. However, I doubt that everybody actually realizes that, so at the end of the day, it's probably not really that special. –  RegDwigнt Oct 30 '10 at 16:57
I'm not sure that pretentiousness is the differentiator in this case. It may be in the case of 'expectorate' vs 'spit'. Even then, if expectorate seems more pretentious it is only because it has a greater number of syllables and is therefor used less frequently - presumably by those with a wider vocabulary and who use more syllables than necessary just to let us know that they can. I don't see this difference in the case of indubitably/undoubtedly. –  mickeyf Nov 1 '10 at 14:11
mickeyf: More syllables doesn't always mean used less often or more pretentious. Consider less-used one-syllable words like rue or vie. People generally tend towards regret or compete. Why one was chosen over another could be any number of reasons over hundreds of years, so it's really hard to say. –  stevendesu Nov 14 '10 at 17:22

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There is actually a subtle distinction between the two words: undoubtedly means "not doubted" whereas indubitably means "beyond doubt" i.e. that which cannot be doubted as opposed that which is not doubted.

This answer serves to illustrate, in part, the more general question you've raised. There is a phenomenal plethora of synonyms in English (Hungarian takes the trophy, though) and it is largely due to the language's mongrel heritage, in turn caused by successive waves of conquerors and invaders putting down roots in the land. We have roots in a number of Celtic, West Germanic and Romance languages, and so an extraordinary arsenal of vocabulary has been available to us. As a result, we have been able to use these synonyms to inject the language with subtler shades of meaning than would be afforded by a single linguistic root. Why this quality is more apparent in English than in some other languages is not entirely clear (we're certainly not unique in our mongrel heritage) and the debate continues among linguists today.

Regarding "pretentious" synonyms, I believe this has its origins in the days when French was the language of the court and Latin that of the clergy, while common old guttural, germanic, dialectic English was the language of the peasantry. The association of Romance languages (and therefore longer words of latin-style inflection) with the higher classes of society has stuck with us, and the hangover of this can be observed, for example, in the extensive use of French in "legalese."

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I think you missed one important part. indubitable ends in able. undoubted simply ends in ed. A word ending in able implies that it is possible. Therefore by appending in (not), it "is not possible" to doubt. By appending in (not) to doubted, however, there is no suffix that implies possibility. Consider instead undoubtable. By adding able we've given it the same meaning as indubitable. –  stevendesu Nov 14 '10 at 17:19

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