Using a Kesuba of a Besula for a Beula:
The Sages established different Kesuba sums for a woman who is a Besula versus a Beula. The Ikkur Kesuba of a Besula is 200 Zuz, while the Ikkur Kesuba of a Beula is 100 Zuz. The following will discuss whether one may use the Kesuba of a Besula for a Kallah who is not a Besula.
Without knowledge of the Chasan: [It is forbidden for a Kallah who is not a Besula to withhold this information from her Chasan and have him obligate himself to a Kesuba of a Besula.] If this occurred, the [entire] Kesuba is invalid. Accordingly, a new Kesuba of 100 Zuz must be written as soon as the Chasan is informed. [Nonetheless, the Kiddushin remains valid even in such a case.]
With knowledge of the Chasan: Some Poskim rule that if a Chasan is informed that his Kallah is not a Besula, he may nevertheless choose to obligate himself to the Kesuba of a Besula, and hence use a regular Besula Kesuba for the wedding. According to this approach, there is no obligation for a Chasan to inform the Misader Kiddushin, or anyone else for that matter, of the status of his Kallah if she is not a Beula, so long as he agrees to obligate himself to the Kesuba of a Besula. However, this only applies if the Kallah did not become prohibited to a Kohen, otherwise, a Kesuba of a Beula must be used. [Nonetheless, initially, it is proper for every couple to use the form of Kesuba that was established for their status, and hence a Kesuba of a Beula should be used in such a case, even if the Chasan does not mind obligating himself to the Kesuba of a Besula. Accordingly, some Misader Kiddushin’s are accustomed to question the Chasan as to the state of the Kallah, prior to writing the Kesuba, and will not use a Kesuba of a Besula for a Beula even with the Chasan’s consent. If the family is embarrassed that a Kesuba of a Beula is being used due to it being read and publicized under the Chuppah, one may prearrange with the reader of the Kesuba to read the Nussach of a Besula.]
A Kallah who is not a Besula must inform her Chasan of this information, and a Kesuba of a Beula is to be written. Nonetheless, some Poskim permit the Kesuba of a Besula to be written if the Chasan is pre-informed and nevertheless consents, and the Kallah has not become prohibited to marry a Kohen. Initially, however, a Kesuba of a Beula is to always be used even if the above conditions are fulfilled.
Must the Misader Kedushin be told that she is a Beula if he is not the person who is writing the Kesuba?
There is no need to inform the Misader Kedushin that the Kallah is a Beuala if he is a different person than the one being Misader the Kesuba.
At what stage must a Kallah inform her Chasan that she is not a Besula?
This information is not to be divulged until the Chasan has shown deep interest in closing the Shidduch and getting married. Some Poskim rule that it is even forbidden to divulge this information on the outset, prior to the first meeting, or prior to a serious development of the Shidduch.
A Segula for Shalom Bayis:
It is known that having a Kosher Kesuba is an imperative Segula for marital harmony. Rav Mordechai Shmuel Ashkenazi za”l, the previous Rav of Kfar Chabad, stated that over the years he noticed that couples who had the Kesuba of a Besula written when in truth the Kallah was a Beula had increased issues in Shalom Bayis, and he hence would tell couples to always use the correct status Kesuba in all cases.
 See Eiyn Yitzchak E.H. 1:67; Igros Moshe O.C. 4:118
 Who is a Beula? A Beula includes any woman who was previously intimate with a man in a way that she is no longer considered a virgin, whether in or out of wedlock, and whether willingly or due to rape. Furthermore, even if she was never intimate with a man, but lost her virginity due to an accident [i.e. Mukas Eitz], she is considered a Beula in this regard and is to receive a Kesuba of 100 Mana. [Michaber E.H. 67:5; Kesubos 11b]
 Michaber E.H. 66:6; Mishneh Kesubos 10b
 Implication of Michaber E.H. 67:5; Eiyn Yitzchak ibid 15; Igros Moshe ibid; Kovetz Teshuvos of Rav Elyashiv 1:159; Even Yisrael 9:133
The reason: As the Kesuba is invalid, and it is forbidden to live with a person without a Kesuba. [Eiyn Yitzchak ibid; Rav Elyashiv ibid; See however Even Yisrael 9:133] Likewise, not telling the Chasan is considered Gneivas Daas. [Rav Elyashiv ibid; Even Yisrael ibid]
Other opinions: Some Poskim give room for the Chasan to not be informed that his Kallah is not a Besula. [See Maharsham 7:152 who gave such a Heter in a time of need, under specific circumstances and conditions; See Even Yisrael 9:133 that it is not considered to be living without a Kesuba, as the Chasan is unaware of its invalidation and will be deterred to easily divorce her]
 This includes both the Ikkur and Tosefes Kesuba. [Darkei Moshe 67; Beis Shmuel 67:4; See Chelkas Mechokeik 67:5 who questions why the Tosefes Kesuba is also invalid]
 Michaber E.H. 67:5; Kesubos 11b
The reason: As this is a classic case of Mekach Taus [a transaction performed under false pretenses], in which case we invalidate the obligation. [Beis Shmuel ibid]
 Rama 68:9; Tur 68; Rambam
 Implication of Rama ibid, Rambam and Tur; Michaber E.H. 39:5 that if he accepted the Mum after discovery, the Kiddushin is valid; Haflah in Kuntrus Achron; Eiyn Yitzchak ibid 2-15 [See there for a thorough analysis on this subject, and his conclusion that according to all the Kiddushin is valid]; Rav Elyashiv ibid; See Even Yisrael ibid
Other opinions: Some rule that the Kiddushin is invalid and needs to be redone. [Tosafus Kesubos 11, brought in Beis Shmuel 68:24; See Eiyn Yitzchak ibid]
 Igros Moshe O.C. 4:118; Heard in name of Rav Z.S. Dworkin regarding Ballei Teshuvah weddings, although this matter has not been conformed
 Writing the term “Deoraisa”: The term Deoraisa written in a Kesuba of a Besula refers to the coinage of the sum obligated and not to the idea that the Kesuba of a Besula is Biblical. [See Rama 66:6; Beis Shmuel 66:14 and Chelkas Mechokeik 66:24 in name of Rosh] Thus, it is permitted to write this term even if she is a Beula.
Writing the word Besula: Tzaruch Iyun regarding how we can allow the term Besula to be written if it is a lie. See however Maharsham 7:152; Igros Moshe ibid.
If the Kallah was intimate with the Chasan: Some Poskim rule that when she lost her Besulim to the Chasan, then certainly the Kesuba of a Besula is to initially be written. [Shemesh Tzedaka E.H. 5, brought in Pischeiy Teshuvah E.H. 177:3; Igros Moshe ibid and E.H. 1:101; See Tur 177; Rambam Naara 8:3 and Mishnhe Lamelech there] However, other Poskim rule she is to have a Kesuba of a Beula written. [Noda Beyehuda Tinyana 33; Pischeiy Teshuvah ibid; Chasam Sofer E.H. 1:133]
 Igros Moshe ibid extends this and says that it is even forbidden to tell them, as it serves no purpose.
 A woman becomes invalid to a Kohen if she had relations with a gentile, or with a forbidden relative or man that she is forbidden to marry, or a Chalal. [See Michaber E.H. 6:8]
 Igros Moshe ibid; See Levush 66:2; Otzer Haposkim 66:145
The reason: In order to inform the public that she is invalid to a Kohen , so she does not come to marry a Kohen if she becomes a widow.
 See Maharsham ibid; Heard from Rav Ashkenazi za”l, previous Rav of Kfar Chabad, as aside for the issue presented in writing a falsehood that she is a Besula, in his experience, many of the couples who he used the above Heter to write the Kesuba of a Besula, later came to him for serious Shalom Bayis challenges, and hence he stopped allowing such Kesubos to be written for a Beula, even with consent of the Chasan.
 So I received from Rav M.S. Ashkenazi za”l, previous Rav of Kfar Chabad, that he would ask each Chasan at the time of writing the Kesuba if the Kallah is a Besula or Beula.
 Maharsham 7:152
 Igros Moshe ibid
 Igros Moshe ibid