Tips for Beginning a Prison Correspondence

Beginning a prison correspondence with an inmate can be challenging, and you must be wondering how to write to a prisoner you don’t know! You will find below some tutorial videos and many tips to help you write to an inmate for the first time..

Our Tutorial Videos:

Check out Sigrid’s videos below for more tips on how to start a prison correspondence!

Our Tips:

Click each tip to access more details and information.

Do not write to an inmate if you're under 18

This is a very important rule to be aware of. Juveniles are a vulnerable population, and no matter how ready you might feel for this, if you are under 18, you might not (yet) have the tools to handle a prison correspondence. Additionally, you could get the prison penpal in trouble for writing to a minor. Please be patient, leave the website now, and wait for your 18th birthday!

Read our precautionary measures to write to an inmate

Just as everywhere else, you can have people in prison with good intentions… and also people with bad ones. Read our precautionary measures to write to an inmate to understand the extent of actions and measures we take with our prison pen pal program to protect the public and the visitors on our website.

Be aware of the commitment

A lot of people behind bars do not have any friends or family on the outside world to care for them, and are extremely lonely. A pen pal can change their life drastically, for good, or, sometimes, for bad. Keep in mind that if being rejected can be tough on someone in the outside world, it can potentially be absolutely devastating for someone behind bars. So be aware that if you choose to write to an inmate with a life sentence for example, you could end up spending decades writing to that person! The commitment is important to consider, because you could end up being the only contact your prison penpal has to the outside world and sometimes their only friend. Of course, in some circumstances, putting an end to a prison correspondence makes sense and is perfectly understandable, but please, always show honesty, and if you no longer want to write, simply say so.

Do not underestimate the importance of a prison correspondence

It is crucial to remember that letters can have a huge impact on someone behind bars. A letter can become something your prison penpal looks forward to every week, and your friendship can eventually give them a sense of purpose. Your words can have tremendous impact, not only in their daily life but also in their transition back to society. Having support and encouragement could be a turning point in their lives.

Provide your mailing address... or not

Many facilities do not have an email system in place where both the inmate and their penpal can email back and forth. For this reason, it might be inevitable at some point to provide your prison penpal with your mailing address. However, if you are not completely comfortable with the idea of revealing your personal address (especially if you are not the only person living there), you can easily set up a P.O. Box! Get in touch with your local post office for more information. Some churches also let the public use their address for their prison correspondence. Obviously, you will need to reach out to them before doing so.

Mind the prison mail rules

Prison mail regulations differ from a facility to another and cannot always be found on the Internet. If you don’t have the option to email a prisoner and have to (or want to) use “snail mail” instead, stay simple, at least in your first letter. You wouldn’t want your letter rejected by the prison administration – especially because, depending on the circumstances, you might never find out that the inmate didn’t get your letter! Use a white envelope, white paper, black or blue ink, no stickers or extra stamps inside of the envelope – basically, just keep it to the minimum. Prison regulations are numerous, and they even seem absurd and frustrating at times. For example, some institutions only give a black and white copy of the letter to the inmate, not even the original! So, do not assume anything, and just keep it simple at first. You can ask your prison penpal about the correspondence rules in your first letter; they should be aware of them, or you can also read our page about the prison mail rules for more information on the subject.

Remember that your mail is being read

Every correctional facility has its own rules and ways to do things. Depending on the institution, your mail to your prison penpal will either be read closely… or not at all. It can also depend on the inmate’s security level. Simply keep in mind that every piece of mail you send to an inmate can lawfully be read (and rejected!) by an institution, at their discretion. Because of this, always be mindful of the things you say in your letters, including jokes. They could be misinterpreted by the staff and get your prison penpal in trouble.

Know how to address your letter

Write on the envelope your prison penpal’s address as indicated on their profile. Do not forget to mention the ID number, or your letter will likely be rejected. Write your name and address on the top left corner of the envelope (most facilities will reject letters if they don’t have the sender’s return address on them). Do not forget to mention your country if you’re writing to an inmate located abroad. Be aware that mail rooms can be overloaded and swamped with mail so it is a good idea to write the last name and ID number of the prison penpal on every document sent, in case it would slip out of the envelope. If it is your first letter and the inmate doesn’t have your address yet, you might also want to write your address somewhere in your letter, in case it gets separated from its envelope.

Be straightforward with your prison penpal

Communicating in writing can lead to many more misunderstandings than with an in-person discussion. For this reason, we strongly advise you to be direct in your letters, especially the first one. Don’t be ambiguous about what you are looking for in a prison correspondence or you might mislead the inmate or create expectations that you will not be able to meet in the long run. Tell them how and why you ended up on Wire of Hope’s website, what you have to offer, how regularly you think you can write, etc. Make your intentions clear and don’t make promises you cannot keep. It is best for both the inmate and pen pal to have a clear understanding from the start and to be aware of what to expect from the correspondence.

Introduce yourself

It is not unusual to run out of topics to talk about in a first letter, not because topics are hard to find (they’re really not!) but because it is not that easy to write a letter to a complete stranger. Don’t be shy, and just give your new prison penpal some information about yourself. Keep in mind that you know a lot about the inmate because of their profile, but they don’t know anything about you! It is a first introduction, so it’s really not about going into details but more about giving some conversation starters for the inmate to work with. They will probably respond your letter by asking tons of questions, and then the conversation will feel more natural and flowing. Usually, the first letter is the hardest; prison correspondence becomes much easier with time. Don’t give up! Here are some topics for your first letter: your personality, age, hometown, job or studies, hobbies, favorite movie/book/music, travels, TV shows, current events, family/friends, etc. Many more topics are suggested in the video “First Letter” above. Take a look!

Show interest

You probably had your reasons to choose this specific profile among all of the ads in our inmate penpal listings, so don’t hesitate to explain those reasons in your first letter. Not only can it be another interesting topic to address, but it will show your prison penpal what exactly in their profile caught your attention and what you liked about what they had to say.

Do not ask questions about their case

The whole purpose of Wire of Hope is to find penpals for inmates, so they can mentally escape their daily life in prison and finally feel human again. Mentioning their crime will only remind them of their situation again and might be something extremely hard to talk about. It is important to realize that everyone has a story. Some parts of theirs (true or not) may have been made public, yet it does not mean that the story doesn’t belong to them anymore. Some inmate penpals may choose never to talk about their offenses, and some will be very open about discussing them. Either way, it is their choice and it should come from them; avoid bringing up the subject yourself, unless you established a trusting friendship first. Also, please note that inmates cannot discuss the details of their cases when these are still pending (which is the case of most death row inmates for example). Wire of Hope has purposely chosen to disclose information about the offenses of the inmates listed on the website. Please make sure to look at the offense(s) before writing. These people are in prison, they have been through a trial already and they don’t need to be judged a second time.

Send a picture when you feel ready

You can choose to send a picture of yourself with your very first letter, but be aware that this could send the wrong message to your new prison penpal, so choose your picture wisely, or simply wait for the inmate to ask you for one. They usually ask pretty early in the correspondence, because they are curious to put a face to their new penpal’s name. If you are not comfortable doing so, once again, don’t be afraid to speak up! But remember that it is only fair for them to ask to see your face when you have already seen theirs!

Speak up when needed

If you feel uncomfortable at any point in your prison correspondence, speak up. Most of the time, problems or misunderstandings can be defused simply by discussing them. For example, a prison penpal may get flirty over time. Keep in mind that a wide majority of them don’t have any contact with the outside world. For this reason, they can easily be carried away and don’t need a lot to start imagining plenty of things. If the flirting makes you uncomfortable, don’t be afraid to let them know right away. If you do not say a word about it, they might end up imagining even more things and developing stronger feelings, which may lead you to stop writing and create a lot of confusion for your prison penpal. If the inmate does not appreciate your honesty and decides to stop the correspondence, then it’s probably a blessing in disguise; you obviously did not share the same expectations.

Do not send money immediately

It is a reality that some inmates have dishonest intentions and may use prison correspondence in order to scam people for gifts or money. They can be extremely creative as to finding ways to ask for financial help, so be smart, inform yourself, and trust your gut! Do not send money (including on their behalf) if you do not feel comfortable to do so or if you’re struggling yourself. Keep in mind that you are already giving them a lot, by investing your time and offering your friendship. Sending money to cover their expenses for stamps is a nice gesture, if you can afford it. A book or a package for Christmas or their birthday will also be highly appreciated, but you might want to wait to have established a strong and trusting relationship before doing so. If your prison penpal asks for something you feel suspicious about, simply don’t do it. Also, remember that the regulations are different from one prison to another so make sure to ask your prison penpal before sending anything (for example, some facilities will let you send some stamps or stationary, but most won’t).

Do not accept money from your prison penpal

You could put yourself in a very critical position if the money was forged. Do not accept money from inmates or on their behalf!

Do not contact anyone on behalf of your prison penpal

Inmates with bad intentions could try to use their penpals to reach out to their victim or potential victims. Do not contact anyone on behalf of an inmate, at least not at the beginning of your prison correspondence and not without making sure of who that person is to the inmate.

Do not write to inmates in the same facility

Unless they gave you their approval to do so, avoid writing to prisoners in the same facility. For all you know, the inmates could be enemies from rival groups/gangs and you could create very serious issues between them. Not only that but they could feel betrayed, especially if they’d shared some personal details of their life with you! This could end up badly, and be very hurtful to your prison penpal.

Do not write to inmates' co-defendants

Whatever your intentions are, writing people involved in the same criminal case is to be avoided at any cost. This could result in a huge mess, and you could end up getting yourself involved in some serious legal trouble. Do not write to a co-defendant, even if your prison penpal asks you to do so.

Be patient!

Whether you sent an email or a handwritten letter, please remember that it is prison, and the mail processing there can be extremely slow. Be patient, especially if you are writing from overseas. Wire of Hope recommends that if you have not received an answer within a month, you can send a short letter to the inmate asking if they have received your first piece of mail. If the inmate still does not answer in the next month, please do not insist and try to find someone else to write to!