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In some siddurim that are printed in certain Hebrew fonts, you will find words such as משה (Moshe) or חשך (darkness) that do not print with two nekudot. The most explicit way to point these words would be to have a holam over the first consonant and a "shin dot" (what's its real name?) over the shin.

Instead, the siddurim I am referring to only put the holam in, not the second dot. In the two examples I give, the ש is indeed supposed to be pronounced as a "shin", but I do not know if this is safe to always assume this. Are there cases where a ש after a holam should actually be pronounced as a "sin"? How would you recognize those cases, a grammatical rule or just knowing the word?

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    עשה שלום במרומיו... – Double AA May 19 '15 at 3:28
  • @DoubleAA Aha, that is a good example and shows how that font handles it and why I didn't recognize it. In that case, the font does print both the holam and the "sin dot". So it seems to drop the second dot for shin, but not for sin. Thanks. – Mike May 19 '15 at 3:33
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    I think this is just a modern printing convention. I wouldn't read too much into it. – Double AA May 19 '15 at 3:35
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See the introduction to the Jerusalem Bible by Koren Publishers.

They go to great lengths to explain how they crafted a font so as to solve the issue you raise: they differentiate between the Cholem and the Shin/Sin dots by height and weight so that you can see both - and not confuse them.

So, as DoubleAA already commented, what you are referring to is simply a convenience of the [manual] typesetter and then perpetuated by the printers.

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    I have also seen variations after a pronounced vav (pronounced vo rather than o) – CashCow May 19 '15 at 9:30

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