3. Machshireiy Milah/Transgressions involved in preparing for the circumcision:[1]

Only the act of circumcision itself overrides Shabbos, while all other matters which are done to prepare for the circumcision may not be done on Shabbos [or Yom Tov[2]] if they involve any Shabbos prohibition, even of Rabbinical nature.[3] Thus all the forbidden preparations for the circumcision must be done from before Shabbos. This includes:

• Making or sharpening the blade of the Mila knife.[4]
• Bringing the knife to the area of the circumcision must be done before Shabbos if it involves passing an area in which carrying is forbidden, whether Biblically or Rabbinically.
• Preparation of medicines, as explained above [although on Yom Tov, at times it is permitted[5]].
• Chaluk[6]

If a person did not do the above before Shabbos: If a forbidden action was not taken care of from before Shabbos, it remains forbidden to do so on Shabbos even if doing so involves a mere Rabbinical prohibition[7], and even if this will cause the circumcision to be delayed until the next day.[8] This applies even if it was beyond one’s control that the above actions were not fulfilled before Shabbos. Likewise, even if the necessary preparations were fulfilled before Shabbos but the items got lost or damaged or the medicine spilled [and it cannot be made without a Shinuiy] and new one’s are required, it nevertheless remains forbidden to be done, and the Mila is rather to be differed until after Shabbos.[9]

Asking a gentile to do one of the forbidden preparations:[10] One may ask a gentile to perform a Rabbinically forbidden action needed for the circumcision.[11] Furthermore, if absolutely necessary to the point that lack of doing so will require delaying the circumcision until the next day[12], one may even ask a gentile to perform a Biblically forbidden act needed for the circumcision.[13]

Asking a gentile to carry the child to Shul:[14] It is disputed whether one may ask a gentile to carry the infant from his house to Shul if the area does not have an Eiruv.[15] Practically those which are lenient are to do as follows: The gentile is to take the child out from his house into the public domain. The child is then to be handed to a Jew which in turn hands it to another Jew within his 4 cubit radius and so on and so forth until the child reaches near the entrance of the Shul.[16] The gentile then takes the child and carries him into the Shul.

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[1] Admur 331:7; Michaber O.C. 331; Y.D. 266:2; See Pesakim Uteshuvos 266:4; See Encyclopedia Talmudit Vol. 46 Erech Mila p. 505

[2] Michaber Y.D. 266:6

[3] The reason: The reason for this is because since these acts can be performed before Shabbos there is no need for them to override Shabbos. [Admur ibid]

[4] Admur ibid; Michaber ibid; Chochmas Adam 135, brought in Pischeiy Teshuvah Y.D. 266:4 regarding sharpening

[5] Michaber Y.D. 266:6

[6] Admur 331:7; Michaber O.C. 331; Y.D. 266:3

A Chaluk is a cloth which has a hole pierced in its middle to be garbed onto the child’s Gid, which is then tightened around the Gid to prevent its skin from covering over the foreskin. Hence this hole may not be made on Shabbos. One may however tie a regular cloth around the Gid without making a hole. Likewise, one may carry it with an irregularity through a Rabbinical forbidden domain such as by wrapping it on his finger. [Admur ibid]

[7] Such as to carry the knife or the infant through a courtyard which did not have Eiruv Chatzeiros done. [Admur ibid]

[8] The reason: As the Sages upheld their decrees even when a Kareis penalty will ensue due to abiding by it. [Admur ibid]

[9] Admur 331:1 [Only if medicine got lost after the Mila may one do it] and 7 [or it was made and got lost] [See Admur 248:5. Vetzaruch Iyun from Admur 248:6!] Michaber O.C. 331:4; Y.D. 266:4 [Only if medicine got lost after the Mila may one do it]; Shach Y.D. 266:6; Bach 266; Rambam Mila 2:8; Rif 55; Ran Shabbos 53a in name of Razah in Hamaor Shabbos 53, and Rashba Shabbos 134b; Beis Yosef 266 in name of Rif and Rambam ibid; Levush 266:4

Other opinions: Some Poskim rule that the Mila is Docheh Shabbos for the sake of making new medicine after the Mila, as the Mila is on time and is Doche Shabbos, and once the Mila is done the Chillul Shabbos is necessary for Pikuach Nefesh. [Shach ibid in name of Ran Shabbos 53a in name of Ramban Shabbos 134; See also Admur 248:5-12 that according to some opinions one may enter a ship for the need of a Mitzvah even though he will later need to be Michalel Shabbos]

[10] Admur 331:7

[11] The reason: As the Sages did not decree against Shvus Deshvus in a case which involves a Mitzvah. [Admur ibid]

[12] Such as sharpening the knife, or to carry it through a public domain. [Admur ibid]

[13] A dispute of this matter is recorded in Admur. Some opinions rule it is forbidden to ever ask a gentile to perform a Biblical prohibition even in the case of a Mitzvah. [1^stopinion in Admur ibid; Michaber Y.D. 266:5] Others however rule that even Biblical prohibitions may be performed through a gentile for the sake of a Mitzvah. Practically although one may not rely on this latter opinion regarding a typical Mitzvah, nevertheless regarding Mila since it itself overrides Shabbos one may rely on their words regarding the prohibited preparations. [Admur ibid]

[14] Admur 331:8; 347:7; See Pesakim Uteshuvos 266:6

[15] As on the one hand the child can be circumcised at his home, and hence bringing the child to Shul involves no Mitzvah need for which the Sages allowed asking a gentile. This would apply even if the area is merely Rabbinically forbidden to carry in such as a courtyard without Eiruv Chatzeiros. Others however allow asking a gentile to bring the child to Shul [through a merely Rabbinically forbidden area of carrying] as circumcising in Shul will gather greater attendance which thereby beautifies G-d. [Admur ibid]

[16] A Jew is not to carry the child from inside to outside or vice versa, even if another Jew will take the child from his hands before he puts the child down, as nevertheless a Rabbinical prohibition has been performed by this Jew, as he has performed Akirah or Hanacha. [Admur ibid]