How many times can I redo Salatul Istikhara?

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Istikhara prayer is more like a form of dua’. The main thing is to fully identify if the matter you seek Allah’s help for is permissible and that you did not ignore the many aspects of what you need to do before asking Allah to help you decide. Considering the fact that you did take all the measures to ensure taking good decisions and are ready to act upon it, but unsure if your measures were good or not, you can go ahead and pray Istikhara prayer and there is no limit to how many Istikhara prayers and dua’ you can make till you feel content.