How to Write an Appropriate Letter to Someone in Jail or Prison

Co-authored by wikiHow Staff

Last Updated: November 26, 2022

Research has shown that incarcerated individuals who maintain contact with supportive family members or friends are in a better position to succeed after their release. By writing letters to family, friends, or even strangers who are incarcerated, you provide these individuals with a link to the outside world and the knowledge that despite the choices they have made, there are still people who care about them and support them. If you know someone who is incarcerated, you should consider writing to him or her in prison but be sure to be clear about how often you can write. If you want to become a pen pal with a prisoner, there are numerous organizations and businesses that can help facilitate that relationship.

Part 1

Part 1 of 3:

Writing to Someone You Know in Prison

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Write on a regular basis. If you know someone in prison, writing that person a letter can help the prisoner to feel connected and supported by family members and friends. It is important to let the person in prison know how often you can write letters. This allows the incarcerated individual to maintain his or her expectations and allows you to manage your busy life.^{[1]
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Ask open-ended questions. Writing letters may be one of the only ways that an incarcerated individual can talk about how he or she is managing in prison. In order to facilitate an open dialogue and let the person know that you are interested in hearing about his or her life, ask open-ended questions. The incarcerated person may or may not choose to respond to the questions. However, by asking the questions you are letting the person know that you are willing to listen. Some questions that you can ask in your letter may include:
- How are you feeling?
- What are you doing to keep busy?
- What can I do to help support you?^{[2]
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3
Provide your spouse or partner with details from your life. Having your partner incarcerated places significant strain on your relationship. It is important to find ways to stay connected to your loved one while the person is incarcerated. It is important to communicate honestly, regularly, and when possible to include your partner in decision-making.
- Tell your partner about your plans and your regular schedule.
- If your incarcerated partner is reading a particular book or watching a particular show, read or watch the same thing and discuss it in your letter. This provides you with a common interest while your partner is incarcerated.
- If you have children, share details about your child’s life.
- Write about decisions that you are trying to make about jobs, school, friendships and ask for your partner’s advice.
- Be clear about what you can and cannot do. For example, if your incarcerated partner wants you to write every day and you are unable to do that, explain that to your partner and talk about your feelings or concerns honestly.
4
Encourage a child to communicate with an incarcerated parent. Often, letters are the main way that a child can communicate with an incarcerated parent. Writing to a parent can help the child express his or her feelings, feel connected to an incarcerated parent or even lay the groundwork for a future relationship with the parent. If a child has difficulty expressing his or her feelings of sadness, loneliness, abandonment, or anger, it is important for a caregiver to help the child find the words and either write or dictate these feelings in a letter. It is important to share details of the child’s life with the parent, including drawings from the child or schoolwork. Potential topics to write about in a letter include:
- Shared interests such as sports, school, or books.
- Current events.
- Special events, such as graduation, birthdays or holidays.
- Favorite memories, particularly about the incarcerated parent.
- Provide updates on the child’s life, such as how the child is doing in school or in extracurricular events.

Part 2

Part 2 of 3:

Writing to a Stranger in Prison

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Consider whether you can make a commitment to an incarcerated pen pal. When you choose to write a prisoner you must understand that you are not engaging in charity but in taking the time to get to know another individual and potentially making a new friend. Therefore, before choosing to write a prisoner you should think about whether you can make the time to maintain the correspondence. It can be incredibly disappointing to an incarcerated person to have someone reach out once or twice and then never hear from that person again.^{[3]
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Locate a prisoner. There are a number of organizations and online businesses that connect individuals with incarcerated people looking for pen pals. You can find these websites by conducting an internet search for the phrase: write to a person in prison.
- Some of these websites charge prisoners a fee for them to sign-up and others may charge users a fee to connect with prisoners.
- These websites may suggest that you use the website for friendship rather than for finding romantic relationships.
- The website may not verify any of the information provided by the prisoner.
- Look to see how long the website/company has been in business.
- Look for online reviews to see whether the company is considered reputable.^{[4]
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Be clear in your intentions. When you write an incarcerated individual, it is important to be clear about your reasons for writing the letter. If you are looking for friendship or to offer support you should state this in your letter. You should also state how often you will be able to correspond to the prisoner.
- Some incarcerated individuals may be seeking a romantic relationship. If you are not interested in pursuing a romantic relationship you should clearly and kindly explain your position.
- Some individuals may ask you for money or to do things for them outside of prison. You can politely refuse the request and explain that you will not be giving them money.
4
Keep your first letter short. When you write your first letter to an incarcerated individual, you should keep that letter relatively short. You can explain who you are and how you got their name. You should also tell the person why you wanted to write to them.
- You should be prepared to maintain the correspondence for at least six months.
- Do not make any commitments that you feel that you can’t meet.
- Make sure that you follow any of the prison’s rules about what can and cannot be included in a letter (discussed below).
5
Offer some details about your life. If you are interested in getting to know an incarcerated person by exchanging letters, it is important that you share some stories or details about your life. You should only share what you feel comfortable sharing. If you think about the pen pal process of getting to know someone, it is important that they get to know you some as well so that they feel a connection to the outside world.
- Your letters will be read by prison officials so it is important to refrain from discussing any criminal activity, or anything else prohibited by prison regulations.^{[5]
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Include your return address. When establishing a pen pal relationship, you need to provide the prisoner with an address where you can receive letters. While many people provide their home address, others choose to keep their home address private and instead set up a post office box (P.O. box). Whichever you choose is fine but generally, prisons require letters to have a return address on the envelope in order for the letter to be given to the prisoner.

Part 3

Part 3 of 3:

Following Prison Regulations Regarding Letter Writing

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Check the prison or state’s website for regulations. Generally, prisons have specific rules regarding what a prisoner can receive in the mail. Before sending a letter to a prisoner, go online and see whether the prison has a website. You should check the website for regulations regarding mail and make sure your letter meets all of the requirements.
- You can find a prison website by searching the internet for the name of the prison and the words: send mail to a prisoner.
- This search should direct you to either a website for a prison or to the governmental entity (state or federal) that manages the prison and sets forth regulations regarding prisoner correspondence.
2
Address the letter properly. While you should follow the specific guidelines for the prison where the incarcerated person resides, typically your letter should be addressed to the prisoner’s legal name, followed by the prisoner’s number. The next line should list the cell/bunk location, if given, followed by the name of the prison. The following lines should include the street address or P.O. Box for the prison followed by the city, state and zip code.^{[6]
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Do not include any prohibited items or content. The prison regulations will outline a number of things that you are prohibited from sending a prisoner as well as topics that you are prohibited from writing about. For example, many prisons prohibit you from sending books directly to an inmate. Instead, the book must be sent from a publishing house or distributor. With regard to the content of the letter, you are prohibited from writing about anything that describes or encourages criminal activity. Some additional items or content that is prohibited include:
- Letters that have staples or paper clips.
- Cash.
- Cards with electronic components.
- Nude photographs or photographs which reveal genitalia, buttocks, or breasts.
- Polaroid photos.
- Any descriptions of physical violence.
- Any descriptions of drugs or other intoxicants.
- Any discussion or description of the use or construction of a weapon.

Annotated Letters and Things to Include and Avoid in Your Letter

Annotated Letter to Someone You Know in Jail or Prison

Annotated Letter to a Stranger in Jail or Prison

Things to Include and Avoid in a Letter to Someone in Jail or Prison

Community Q&A

Question

Why is cash not allowed in prison letters?

Community Answer

Cash would be of little use for an inmate beyond bribing a guard or staff member, as all transactions come from the money on an account linked to an inmate.
Question

If I write to show approval of what an inmate did to land in prison, will it be rejected?

Community Answer

It depends on the state and how vindictive they are feeling in the prison. In general, no, but I wouldn't risk it if you aren't willing to lose contact with the inmate.
Question

Can I send postage stamps with my letter?

Community Answer

Yes, you can, although there's no guarantee the inmate will be able to keep them.