Istikhaarah prayer is a Sunnah which the Prophet (peace and blessings of Allaah be upon him) prescribed for anyone who wants to do an action but is hesitant about it.

The scholars are unanimously agreed that Istikhaarah is Sunnah. The evidence that it is prescribed is the hadeeth narrated by al-Bukhaari from Jaabir (may Allaah be pleased with him) who said:

“The Messenger of Allaah (peace and blessings of Allaah be upon him) used to teach his companions to make istikhaarah in all matters, just as he used to teach them soorahs from the Qur’aan. He said: ‘If any one of you is deliberating about a decision he has to make, then let him pray two rak’ahs of non-obligatory prayer, then say
 
The reason why Istikhaarah is prescribed is that it is submission to the command of Allaah and a practical demonstration that one has no power and no strength of one’s own. It means turning to Allaah and seeking to combine the goodness of this world and of the Hereafter. In order to achieve that, one has to knock at the door of the King, Allaah, may He be glorified, and there is nothing more beneficial in this regard than salaah (prayer) and du’aa’ (supplication), because they involve venerating Allaah, praising Him and expressing one’s need for Him. Then after praying istikhaarah one should do that which one feels is best.

In what circumstances should one pray istikhaarah? The four madhhabs are agreed that istikhaarah is prescribed in cases where a person does not know the right decision to make. In matters where it is known whether a thing is good or bad, such as acts of worship, doing good deeds, sins or evil actions, there is no need to pray istikhaarah in these cases.

Istikhaarah is not ordinarily required with regard to things that are recommended, rather it should be done in cases where there is a conflict, i.e., when a person has a choice of two things and must decide which one to start with or which one not to do. With regard to permissible things, he may pray Istikhaarah as a regular matter.