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Breaking a cup/plate:[1]

Some communities are accustomed to break a [glass[2]] cup during the time of the Chuppah. Others place a black cloth, or other symbol of mourning, on the head of the Chasan. Practically, the widespread custom today is to break a glass cup.[3] [The cup should be whole and complete, and one should not choose a chipped or damaged vessel for this purpose.[4]] The cup is customarily broken after the Sheva Brachos.[5] [It is also customary of Ashkenazi Jewry to break a plate by the Tanaim/Vort.[6]] Some are accustomed to recite the verse of Im Eshkacheich Yerushalayim, and have the Chasan repeat after him word after word. This is a good custom.[7] [Some Rabbanim have come out against the customary shout of Mazal Tov, as the glass is broken, as it uproots the entire purpose of the breaking of the glass as a sign of mourning.[8]]

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[1] Rama O.C. 560:2; E.H. 65:3; Tosafos Brachos 31a

[2] Avnei Shoham 51; P”M 560 M”Z 4; Shaareiy Teshuvah 560:3; Moed Lekol Chaiy 10:96; Kaf Hachaim 560:21

The reason: We break glass material as a sign that just as glass can be reformed, so too the Temple will be rebuilt. [P”M ibid]

[3] Rama E.H. ibid that so is the Ashkenazi custom; Shulchan Gavoa 560:5 and Kaf Hachaim 560:21 that so is custom of all; Aruch Hashulchan 560:2; Yalkut Yosef Sova Semachos p. 86; Rav Yaakov Yosef; See however Or Letziyon 3:277 who protests the fact the Sefaradim do not keep this custom

[4] P”M 560 M”Z 4; Moed Lekol Chaiy 10:96; Kaf Hachaim 560:21

[5] Rama E.H. 65:3

[6] Elya Raba 560:7; P”M 560 M”Z 4; Shaareiy Teshuvah 560:3; This is not practiced by Sefaradi Jewry. [Rav Yaakov Yosef]

[7] Taz 560:4

[8] Rav Ovadia Yosef, and his son Rav Yaakov Yosef