Praying two rak'ahs of the istikhaarah prayer for two separate issues
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Question: Is it correct to pray the two rak'ahs for the istikhaarah (prayer) for two separate issues?

Response: You should pray two rak'ahs for the istikhaarah (prayer) for something specific, then you should pray (another two rak'ahs for) the istikhaarah (prayer) for another matter; This, also being in addition to the (istikhaarah) supplication, and two rak'ahs (for the istikhaarah prayer) are not sufficient for two separate issues.

Shaykh 'Abdur-Razzaaq 'Afeefee
Fataawa wa Rasaa.il Shaykh 'Abdur-Razzaaq 'Afeefee - Page 410, Fatwa No.14