Is it permissible to supplicate after the Istikhaarah (guidance-seeking) prayer for several needs? Some examples include staying in a country, remaining with a current employer or seeking another in the same country as opposed to returning to my homeland or some other country, marrying or not, etc.

All perfect praise be to Allaah, the Lord of the worlds. I testify that there is none worthy of worship except Allaah and that Muhammad, sallallaahu ‘alayhi wa sallam, is His slave and Messenger.

The Istikhaarah prayer is recommended when one wants to do something permissible. The Hadeeth that signified the legitimacy of this prayer is narrated by Al-Bukhari and others . Nothing in the words of the scholars explicitly indicates the impermissibility to consult for several matters in a single Istikhaarah prayer.

An-Nawawi while commenting on Saheeh Muslim, said: "It (the Hadeeth) signifies that it is recommended to perform the Istikhaarah prayer when one wants to do something (permissible), whether its goodness is apparent or not."

Al-‘Ayni while commenting on Saheeh Al-Bukhari, said: "He should mention what he wants, such as saying: 'If You know that such matter about travel, marriage, etc…'"

Al-Mubarakfoori while commenting on Sunan At-Tirmithi, said: "When he intends something of marriage, travel or something else of what he wants to do or not to do… (He should perform the Istikhaarah prayer.)"

Consequently, you should mention the matter you intend to do, such as staying in a certain country, saying: “O Allaah, if You know that staying in this country is better for me, for my religion, and for my life…” You should do likewise with other such needs. However, it is better to consult Allaah Almighty, in each one of your affairs alone, as this is easy for you. Also, you will benefit from the several prayers and supplications, as there are much blessings and goodness in them. Nevertheless, if you want to pray a single Istikhaarah prayer for several needs, there is no evidence signifying that such an action is impermissible. 

Allaah Knows best.