How to Write A Letter To An Incarcerated Person

February 24, 2025
9:16 am

Have you ever thought about what a simple letter could mean to someone behind bars?

For many incarcerated individuals, letters are their only connection to the outside world a source of hope, comfort and human connection.

Your words can make a real difference, whether you’re writing to a loved one, an old friend, or a stranger through a prison pen pal program.

But before you start writing, it’s important to understand the right way to communicate following the rules while still making your message heartfelt and meaningful.

Wondering how you write someone in prison in a way that is meaningful and appropriate?

This guide will walk you through the process and help you create a heartfelt and thoughtful message.

Why Exchanging Letters with Incarcerated Individuals Matters

We all know that prison is a lonely place where a simple letter can make all the difference. Many incarcerated individuals in the prison rarely hear from friends or family, which makes receiving letters incredibly special.

Whether you’re writing to a loved one or looking for a prison pen pal, your words can offer encouragement, support and a much needed reminder that they’re not forgotten

Something as small as a heartfelt note can brighten their day and give them hope.

How to Write a Letter to an Incarcerated Person

1. Find an Incarcerated Person to Write To

Don’t know someone in prison? Don’t worry! Various organizations facilitate prisoner letter writing.

Platforms like prison pen pal programs connect volunteer inmate pen pals with inmates who are seeking correspondence.

Be sure to choose a reputable prison pen pal program that prioritizes safety and ethical communication.

2. Follow the Prison’s Mailing Rules

Before you send a letter, take a minute to check the prisoner’s rules. Every facility has its dos and don’ts regarding what you can send, how you format your letter and what’s allowed inside.

Some common restrictions include:

No stickers, glitter, or decorative paper
No cash or contraband
Limited number of pages per letter
Approved envelopes and ink colors

Ignoring these rules could result in your letter being rejected, so it’s important to verify them in advance.

You can check the prison’s mail rules by doing a simple internet search for “mail at ______ prison” or by calling the prison directly.

Most prisons don’t allow things like crayons, glitter pens, permanent markers, colored pencils, stickers, paint or even scented letters.

So, be on the safe side and stick to black or blue ink whether typed or handwritten, on plain white paper in a simple white envelope.

If you’re sending photos or drawings, make sure they’re no bigger than 8*10 inches.

3. Start with a Warm and Positive Tone

Set a friendly tone by starting with a simple “Hello” or “I hope this letter finds you well”.

Look! Many inmates receive little to no mail, so a kind greeting can go a long way. If you’re reconnecting with someone, express your happiness in writing to them again.

4. What to Write to Someone in Prison

Not sure what to say? Here are some ideas:

Ask about their well being – “How have you been holding up?”
Share updates about your life – Talk about everyday moments, like work, hobbies or current events.
Offer words of encouragement – “You are strong, and you will get through this.”
Discuss mutual interests – Books, music, sports, or any common passions.
Keep it light when possible – Avoid overly negative topics that may bring down their mood.

5. Be Mindful of Sensitive Topics

See! It’s important to be open and avoid topics that could trigger emotional distress. Stay away from discussing their case unless they bring it up.

Avoid discussing illegal activities or anything that could be considered threatening.

Instead, focus on positive and uplifting conversations that help them feel valued and included in the world outside.

Here is a simple checklist of topics that you should avoid in your letters:

Their case or illegal matters (unless they bring it up)
Illegal activities or anything that could be seen as suspicious
Escape plans or discussions about prison security
Other inmates or prison staff
Anything that could trigger emotional distress
Gang related language and reference
Negative news that might add to their stress

6. Sign Off with Encouragement

End your letter on a hopeful note. “Looking forward to hearing back from you” or “Sending you strength and positivity” leaves a lasting impression. Let them know they are in your thoughts and that you genuinely care.

How to Make an Inmate Feel Special?

Being in prison can feel lonely, but a thoughtful letter can make someone’s day. As an inmate pen pal here’s how you can make an inmate feel valued and appreciated:

Use Their Name: A simple “Hey (Name) makes it personal and warm.

Share positive updates: Talk about positive moments happening in your life, like funny moments, hobbies or new things you’ve learned.

Encourage Team: Remind them they’re more than their current situation. Share uplifting quotes or words of support.

Ask Questions: Show genuine interest in their thoughts and experiences. It makes the conversation feel two sided.
Show meaningful extras: If allowed, include photos, poems or drawings to brighten their day.

Stay Consistent: Regular letters give them something to look forward to, making them feel remembered and valued.

Additional Tips for Writing a Letter to an Incarcerated Person

inmate pen pals

Write legibly – Some facilities scan letters before delivering them, so make sure your handwriting is easy to read.
Avoid promises you can’t keep – If you say you’ll write regularly, try to follow through.
Respect boundaries – Some inmates prefer casual friendships, while others seek deeper connections. Let the relationship develop naturally.
Use your first name only if writing to a stranger – For safety reasons, avoid sharing personal details in your initial letters.

How Do You Write Someone in Prison Safely?

If you’re looking for a prison pen pal, safety is important. Use a P.O. Box instead of your home address and be cautious about sharing personal information until you feel comfortable. Many letter exchanges result in genuine friendships, but it’s always best to prioritize your well being.

The Power of a Letter

A letter can mean the world to someone behind bars. Whether it’s a friend, family member, or someone you’re just getting to know through a prisoner letter writing program, your words have the power to uplift and inspire. If you’ve been considering exchanging letters with incarcerated individuals, take that step—you might be surprised at the impact it has, both for them and for you.

FAQs

1. Can I send pictures or gifts in my letter?

It depends on the prison’s regulations. Some facilities allow photos, but they may have size restrictions. Gifts, including cash, are generally not allowed.

2. How often should I write to an inmate?

This depends on your availability and comfort level. Some people write weekly, while others send letters once a month. The key is consistency.

3. What if I don’t get a response?

Not all incarcerated individuals have access to writing materials or postage. If you don’t receive a response, don’t take it personally. They may still appreciate your letter.

4. Are prison pen pal programs safe?

Reputable programs have guidelines to protect both writers and inmates. Always follow recommended safety practices, such as using a P.O. Box and avoiding oversharing personal details.