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The Mishneh Berurah (493:5) rules that even those who have the custom not to cut hair or shave during the first half of the sefira are permitted to shave/have a haircut when Rosh Chodesh Iyar falls on a Shabbos.

ואף להנוהגין איסור גם עד ר"ח אייר מ"מ אם חל ר"ח בשבת כיון שיש כאן תוספת שמחה שבת ור"ח יש להתיר להסתפר בע"ש מפני כבוד השבת וגם לישא אשה בו ביום כיון שעיקר הסעודה יהיה בשבת ור"ח

Many have the custom to follow the ruling of R' Yehuda HaChassid not to shave on Rosh Chodesh. The Mishneh Berurah (260:7) cites a custom that this applies even on Friday, notwithstanding the consideration of Kavod Shabbos.

יש מקומות שאין מגלחין ואין נוטלין צפורנים בר"ח אפילו חל ביום עש"ק כי כן צוה ר"י חסיד

In light of the above, would the leniency of the MB to shave when Friday coincides with Rosh Chodesh Iyar apply even when Friday is also Rosh Chodesh?

[Obviously, this question is only relevant for those who generally follow R' Yehuda HaChassid. For those who have the custom to disregard his rulings, the leniency obviously applies.]

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    Considering that nowadays the first day of Rosh Chodesh Iyar cannot be Shabas, the Mishna B'rura must have been talking in 493 about the case that Friday, too, is Rosh Chodesh Iyar. However, that doesn't answer your question, since maybe 493 is disregarding R. Y'huda Hachasid. – msh210 Apr 21 at 10:12
  • Those who understand Hebrew might enjoy this video analysing the question: youtube.com/watch?v=BF1WWCm2hdM – mbloch Apr 21 at 12:32
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R' Moshe Feinstein (Igros Moshe OC 6, §36) is lenient in the above case. He posits that the prohibition of R' Yehuda HaChassid to shave on a Friday Rosh Chodesh applies only when it was possible to shave for Shabbos on Thursday. However, in a situation where it was forbidden to shave up until Rosh Chodesh (like Sefiras Haomer), it would be permitted to shave on Rosh Chodesh too.

R' Yaacov Kaminetzky (Emes L'yaakov, OC 260) agrees, and rules leniently.

Other grounds to be lenient include the ruling of the Darkei Teshuvah (quoted in Shemiras Haguf veHanefesh, 68:9) that when there are two days of Rosh Chodesh, R' Yehuda HaChassid's prohibition to shave applies only on the second day. Accordingly, when Rosh Chodesh is on Friday and Shabbos, it would be permitted to shave on Friday.

However, R' Eliyashiv and the Steipler (quoted here) ruled otherwise, forbidding shaving on Friday Rosh Chodesh Iyar. They understood that the MB was talking only to those who do not follow R' Yehuda HaChassid.

Some poskim do not allow shaving on Friday Rosh Chodesh, but do permit shaving on Thursday after Chatzos, which is still Kavod Shabbos and Rosh Chodesh, but does not require transgressing R' Yehuda HaChassid's ruling. R Eliyashiv disagreed with this ruling.

Sources: R' Yom Tov Zanger, http://beinenu.com/sites/default/files/alonim/197_26_80.pdf

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In the "Even Yisrael" edition of Mishna berurah, I remember that they had a note from Dayan Fisher that the minhag (in Jerusalem at least) is not to be lenient like the Mishna berurah. I believe there is also discussion regarding R' Yehuda HaCHassid's concern as well.) If I can track down the sefer I'll try to copy the note here for you.

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