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In the Name of Allaah, All Compassionate, All Merciful
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Repeating the istikhaarah prayer
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Question: Is repetition of the istikhaarah prayer legislated?

Response: Repetition of the istikhaarah prayer is legislated if the heart is not at ease with either of the two choices after the first prayer.

Shaykh 'Abdur-Razzaaq 'Afeefee
Fataawa wa Rasaa.il Shaykh 'Abdur-Razzaaq 'Afeefee - Page 410, Fatwa No.15