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The Al Chet that we say four times on Yom Kippur - the long list of sins that we list and ask to be forgiven for - is a double-acrostic (in nusach Ashkenaz). Each letter is represented twice in a row (aleph, aleph, bet, bet, etc.) except for samech (ס), which is replaced by sin (שׂ). I would say it's a cute pun in English (sin/sin), but there must be a more believable reason for this.

Why do we replace samech with sin in the Al Chet?

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related judaism.stackexchange.com/questions/4286/… –  Danno Sep 16 '13 at 2:12
In addition to Danno's link, the words with the roots from sikkur (e.g. אמר רבי יוסי מה תנינן סוקרין מה תנינן מהלכין in Y'rushalmi Nidda 3:2) and si'ach (e.g. אמר ר' יוסי סח לי נימוס אחיו של ר' יהושע הגרסי in B'choros 10b) are found spelled both ways. I wonder if an early version of the al cheits uses a spelling with samech. –  Fred Sep 16 '13 at 2:20
@Fred that's fascinating! –  Charles Koppelman Sep 16 '13 at 2:26
Sin and samech get exchanged all the time. Even in Tanach! They were the only two graphemes for a long time which were pronounced identically. In some masoretic manuscripts, a shin is turned into a sin by drawing a little samech on top –  Double AA Sep 16 '13 at 2:56
The Avodas Yisroel siddur of Baer in the inclusion in the Amidah for Chanukkah has the word that we spell עוסקי spelt as עושקי. In the Birkas HaTorah he has לעשוק בדברי תורה. The Gemoro, he says, uses a samech to avoid the confusion of the intended sin with a shin because the Gemoro was not pointed. But in a pointed siddur, he sees not need to use a samech. Perhaps someone can apply his reasoning to this case. –  Avrohom Yitzchok Sep 16 '13 at 20:40

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