Answered by Shaykh Shuaib Ally
Question: Assalam alaykum,
During Ramadan I broke one fast and I know I need to fast for 60 consecutive days as expiation. I failed. Does that mean I have to start again?
Answer: Wa alaikum assalam wa rahmatullah,
When is Performing the Expiation Obligatory?
If a man breaks his Ramadan fast by having sex, he must perform an expiation. This expiation is to free a female, sound, Muslim slave. If one cannot be found, one must fast two months consecutively.
Failing to Fast Two Months Consecutively
If you are required to fast two months consecutively as expiation, and fail to do so, even if it is the last day, and even if it is for just cause such as traveling or illness, or forgetfulness, the school requires you start the count over and fast two months consecutively.
If one is unable to do this because of old age, chronic or long-term illness, for fear that an illness will worsen because of extended fasting, or because one’s extreme desire for sex prevents them from being able to complete the period, they can instead feed sixty people in need.
The standard for inability is fairly high. Taking the foregoing into consideration, one should assess one’s own circumstances to determine if they fall within one of these exceptional cases.
Source: al-Hawashi al-Madaniyyah