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Question: Around the time of Rosh Hashana, I will not be in the proximity of people who can do Hatarat Nedarim for me. Can I do it via Skype?

Answer: While a general Hatarat Nedarim (=HN) within days of Rosh Hashana is just a minhag (see Chayei Adam 138:8), it is good that you are looking for an opportunity to do it.
There is a machloket Rishonim (see Beit Yosef, Yoreh Deah 228 and Ran, Nedarim 8b) whether hatarat nedarim (=hn – annulling (a)specific oath(s)) requires the presence of the oath taker (noder). Thegemara (Nedarim 8b) asks whether a husband can be an agent to request his wife’s hn and concludes that he can. Some say (including R. Shimshon) that others, who are less impacted by it, are certainly effective based on the general rule that agents can carry out halachic processes. The Rambam (Shvuot 6:4), accepted by the Shulchan Aruch (YD 228:16), is among those who require the oath taker’s presence.
We must see how absolute this ruling is, on a few levels. The Keren Ora (Nedarim 8b) and Kiryat Melech Rav (on the Rambam ibid.) suggest that it is a Rabbinic law, with the latter explaining that we want the noder to be self-conscious, to discourage making this a common practice. Rav Auerbach (Minchat Shlomo, Nedarim ibid.) suggests that it is to enable effective discussion of the grounds for the hn.
Classical poskim suggest exceptions. The Rama (YD 228:16, based on the Yerushalmi) says that the hn can be done through an interpreter, but the Shach (228:29) and Taz (228:21) say that this is only because the noder is present. More significantly, the Taz (228:20) cites the Rashba who says that even those who disqualify an agent allow thenoder to submit his request to beit din in writing. The idea is that the request must be transmitted without using intermediaries, but it works even without formalistic interaction between the noder and the beit din. The Taz also cites the Rivash (370), who disallows writing. (The Rivash’s proof is from the midrash about Yiftach’s haughty refusal to go to Pinchas to undo his oath, which seems to indicate that a letter would not have sufficed.) The Taz does not take a clear stand on hn by letter, and the Pitchei Teshuva (228: 9; see also Kol Nidrei 19:3) allows it in a case of significant need.

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164 - Hatarat Nedarim by Skype

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Poskim have been discussing the use of telephones for halachic matters. One crucial issue is appointing the facilitators of a get. This a more difficult matter than ours because of the need to ascertain identity and for a possibly higher level of connection between the husband and the facilitators (see discussion in Tzitz Eliezer X:47 and article by Rabbi H. Jachter in Techumin XIV). Another area of interest is berachot heard via telephone. One cannot fulfill mitzvot through such a beracha, but leading poskim have argued whether one can (Yechaveh Da’at II:68) or cannot (Minchat Shlomo I:9) answer "Amen." Hn by phone could follow the same logic, or can be more lenient (if a practical rather than formal connection between the two is enough) or more strict than other applications (if presence is a Torah requirement).
A Skype discussion is no worse than a written request for hn. After all, one’s written word does not have a special status in this context (proof of this claim is beyond our present scope). Rather, the important thing is to convey the requester’s message effectively without another person’s intervention. In some ways, Skype is preferable. It allows for give and take between the parties and creates a personal connection that could provide a measure of self-consciousness (see above). In the latter, it might even be a slight improvement over telephone. Audio/video’s greater improvement is in regard to cases (arguably, gittin)in which authentication is crucial, as it is easier to impersonate a voice than a voice and appearance.
In conclusion, when necessary, one can rely on hn by phone (see Shevet Hakehati IV:239) and by Skype. We note briefly that HN before Rosh Hashana may require less halachic precision, and therefore leniency is fully acceptable.

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