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Is there a specific minhag regarding when and in what order to eat the simanim? In other words, is it acceptable to serve simanim as a matter of course (leeks with the steak, date cookies for dessert, etc.) or should they be served in their own special time?

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The blessings are prioritised (in general, not just on RH). First "Pri ha-etz". Then "Pri ha-adamah". Then "Shehakol". In "Pri ha-etz" priority is given to "7 species" fruits. Within these, the priority is given to the closest to the word "eretz" - land. Thus the priority is olive, date, grape, fig, pomegranate. "From an article by Rav Eliezer Melamed (in Hebrew)"

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    −1. The question was (in part) whether the siman foods must be eaten separately or can be eaten in the course of the meal. Note that no blessing is recited on most foods eaten in the course of a bread meal, which means that this answer does not address the question. – msh210 Sep 16 '15 at 5:36
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    @msh210 Yet people who eat the simanim before the meal, even after hamotzi, do day berachos because they are not part of the meal. – andrewmh20 Sep 16 '15 at 9:33
  • @andrewmh20 I have never witnessed anybody say a separate bracha for the simanim other than ha'etz. I believe those would be unnecessary and improper. – Daniel Sep 16 '15 at 12:15
  • There are siddurim and "Simanim cards" that quite specifically specify ha'adamah and shehakol. This is after kiddush and before hamotzi. – Epicentre Sep 16 '15 at 12:32
  • @Epicentre Ah, yes, I'd forgotten that some eat them before the bread. Nonetheless, this answer is assuming that that's the case and then addressing what order to eat them in, whereas the question was whether in fact there's a specific point that the siman foods are eaten. – msh210 Sep 16 '15 at 16:54

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