Sisters Corresponding With Brothers in Prisons

Question: Is it permissible for female sisters to write brothers who are in prison (may Allah سبحانه وتعالى hasten their release)?

Islam came with guidelines, rules and principles that scholars derived from the study of the Koran and hadith.
Among those principles are what Imam Ahmad, Malik, Ibn Taimieh and others established under (سد الذرائع  ) which is the rule of avoiding something permissible that may lead to a prohibited/haram matter.
Another principle of Islam is (درء المفاسد مُقدّم على جلب المصالح), which means when the evil is greater than the benefit, then leave the benefit as much as possible.  One need not achieve it since it’s buried in the greater evil.
A third principle of Islam is   (ما أفضى إلى مُحرّم فهو مُحرّ), which means whatever leads to haram becomes in itself haram.
Based on the above mentioned principles of Islam, one should avoid corresponding with inmates of the opposite sex.
Most, if not all, the time, females writing male inmates start off with good intentions, but then the shytan enters, instigating and making a person think it’s only an innocent pen pal, or one can earn great reward for writing our beloved brothers in prison, or maybe instill the hope of marriage.
There may be a benefit to writing someone of the opposite sex, but that leads to excessive communication and possibly even haram.

This is generally the rule in communication between opposite sexes via the internet or otherwise, but even worse when a brother is in prison and has not had any form of contact with a female for years possibly even decades.  The handwriting, or the mere smell of the letter from a female becomes in itself fitnah for the brother in prison–let alone anything that lonely brother may misconstrue or take out of context.
There is no denial that there is benefit from writing brothers in prison, but at the ultimate end the evil is worse.  Just like alcohol.  There is a benefit as Allah سبحانه وتعالى said, but the evil outweighed the benefit and so it was deemed haram.
Shortly before leaving prison, a sister was writing a brother words to boost his eman and encourage him.  The letters went on and the fitnah began.  The brother awoke to realize his error, stepped back, and wrote the sister that this cannot continue on and that he needs to speak to her wali to ask for her hand in marriage.  The problem was eliminated when the family accepted and he only had a short time left in prison and was released. He later married her.  However, not many situations turn out like this.
One should not say, “I know I’m strong and will not fall in the fitnah.”  One must stay away from areas or matters of fitnah and not go near them thinking he/she is strong.  That is why the Prophet صلى الله عليه وسلم‎ said: “When you hear of the dajjal, stay away as much as possible because a man goes to him thinking he is a strong believer and the dajjal stays after him with doubts until he follows him.”

قال عليه الصلاة والسلام : ” من سمع منكم بخروج الدجال فلينأ عنه مااستطاع ، فإن الرجل يأتيه وهو يحسب أنه مؤمن ، فما يزال به حتى يتبعهمما يرى من الشبهات “. رواه أبو داود وغيره

The word used in the hadith فلينأ means ‘stay away from areas of fitnah.’
What many claim to be pure intentions does not justify an action that opens a door to fitnah. Therefore, one should shut this door in order to avoid falling into the prohibited.
The devil starts with communicating then goes further to get to know each other, then a relationship, then heart attachments, then what has major consequences. 
In the matter of writing the inmates, the issue is easily solved when sisters write through their mahram/guardian by using their names and letting them see the correspondence (i.e. brothers, husbands, or even organization names).  I personally received hundreds of letters with no sender names. By doing this, we are fulfilling our obligation of staying in contact with our imprisoned brothers without causing fitnah.
So, if the purpose is really genuine for the sake of Allah, then a sister would never have a problem not putting her name or using a mahram or organization’s name to eliminate this entire ordeal.
By Ahmad Musa Jibril... HA)