He swore oaths repeatedly and broke them; should he offer one expiation or several?

Praise be to Allah.

Firstly: 

Your dislike of what is haram and your swearing by Allah to give it up, are indicative of the goodness and faith in your heart, and your fear of Allah, may He be exalted. We ask Allah to strengthen your faith and increase your resolve, to divert evil away from you and make it easy for you to get married and remain chaste. 

We advise you to turn to Allah and to ask Him a great deal to protect your religious commitment and faith, and to protect you from temptations both apparent and hidden. 

Secondly: 

If a person swears an oath repeatedly about the same thing, then breaks it, he must offer expiation once.  

Shaykh Ibn Baz (may Allah have mercy on him) was asked: I am a young man who swore to Allah more than three times that I would repent from a haram action. My question is: Do I have to offer expiation once or three times, and what is my expiation? 

He replied: You have to offer expiation once, which is to feed or clothe ten poor persons or to free a slave. The one who cannot afford to do that must fast for three days, because Allah says (interpretation of the meaning): 

“Allah will not punish you for what is unintentional in your oaths, but He will punish you for your deliberate oaths; for its expiation (a deliberate oath) feed ten Masaakeen (poor persons), on a scale of the average of that with which you feed your own families, or clothe them or manumit a slave. But whosoever cannot afford (that), then he should fast for three days. That is the expiation for the oaths when you have sworn. And protect your oaths (i.e. do not swear much)” [Al-Maa'idah 5:89]. 

The same applies to all oaths to do one particular thing or not to do one particular thing; if it is done repeatedly, expiation is to be offered only once, if it is not offered the first time it happens. But if a person offers expiation the first time, then he swears the oath again, he must offer expiation again if he breaks the oath. If that happens a third time, after offering expiation for the second time, then he must offer a third expiation. 

But if he swore a number of oaths concerning a number of actions, or giving up a number of actions, then he must offer expiation for each oath, such as if he said ‘By Allah I will not speak to So and so’ and ‘By Allah, I will not eat a certain type of food,’ and ‘By Allah I will not travel to such and such a place’ or ‘By Allah I will speak to So and so’ and ‘By Allah I will hit him’ and so on. 

What must be given to each poor person is half a saa’ of the local staple food, which is equivalent to approximately one and a half kilograms. 

With regard to clothing, it should what is sufficient for praying in, such as a shirt or an izaar and rida’ (lower garment and upper garment). If he offers them dinner or lunch, that is sufficient, because of the general meaning of the verse quoted above. And Allah is the Source of strength. End quote from Majmoo’ Fataawa al-Shaykh Ibn Baz (23/145). 

Thirdly: 

With regard to your saying that when a person dies or is martyred he remains suspended until the oath is fulfilled, if you mean expiation, i.e., that he is detained or suspended because he did not offer expiation, because the Prophet (peace and blessings of Allah be upon him) said: “The martyr will be forgiven for all sins except debt” (narrated by Muslim), 

The answer is that what is meant by debt here is anything that is owed to humans. 

Al-Nawawi (may Allah have mercy on him) said in Sharh Muslim: “except debt” refers to all rights owed to humans, for jihad, martyrdom and other good deeds cannot expiate for debts owed to humans, rather they expiate for debts owed to Allah, may He be exalted. Ends. 

If a person owed expiation for breaking a vow but he did not pay it before he died, then it should be paid from his estate before it is divided. 

And Allah knows best.