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You've Got (Jail) Mail!

A guide to writing pen pals using electronic mail!

It’s important for prisoners to stay in touch with their loved ones. Regular contact with a close friend, family member or partner provides support, motivation and a positive tie to the outside world. Caring, stable relationships have also been directly linked to lower rates of offending – so facilitating prisoners’ communication with people in the community benefits everyone.

These services have been expensive in the past and they tend to be “glitchy” at best. There is improvement on the horizon and much of this is because prisons have discovered that it is cost effective for them to provide tablets to prisoners at no charge. Additionally - the cost of electronic mail “stamps” has been greatly reduced in many prisons across the country and this makes it so much easier for friends and family to communicate and stay connected. In some cases, prisoners have access to video visits and text messaging

Many prison and jail facilities have signed up for JPAY electronic mail. It is mostly state operated prisons. Many private “for profit” prisons are not working towards this goal. Some of these facilities are offering “tablets” with limited internet use to prisoners at no cost and others are charging between $20 and $60. If your pen pal doesn’t have a tablet, they will have access to the kiosk to check, read and send emails.

You can sign up for an account using a “civilian” email address and then you can search for your pen pal by using the State they are being held in and their DOC number. You can use your regular email or create a special email account for penpalling.

The most popular email providers are JPay, SmartJailMail and GettingOut. Signing up for an account requires verifying your email and sometimes a phone number. You will be asked for a physical address and may have to verify your age, but they do not ask for identification unless you are trying to send money. You can then purchase electronic “stamps” and you can send an email with a return electronic “stamp” that can only be used to reply to YOUR emails at no cost to your pen pal. You can also transfer these electronic stamps to your penpal so they can use them to contact their family or friends.

Top Ten Pen Pal Tips for Jail Mail

1. Tell them a little about yourself!

Why you are interested in corresponding: This can be as simple as “I used to be involved in the adult industry, and I want to connect more with folks from our community behind bars” or “My cousin was in jail a while ago, and I know that our criminal justice system is often unjust, there are a lot of rad people behind bars, and “ or “SWOP Behind Bars shared your contact information and that you were looking for support around [writing/GED/substance recovery/reentry]. I’ve also struggled with this and only got through it with a great support system, and I’d love to ‘pay it back.’”

2. Tell them how you heard about them!

Nobody feels good about getting strangers just popping in with no explanation so let them know you heard they wanted a pen pal from SWOP Behind Bars. We only provide penpals to incarcerated people who ask for them!

3. Connect with them with shared experiences, similar hobbies or interests or tales about your travels!

If you want to connect with someone because you share experiences, some ways to do this might be:

  • Talking about your own work or substance use in past tense.

  • Describing your own experiences/work as that of a friend or family member.

  • Describing the legal aspects or equivalents of your own work or experiences -- whether that is fetish/adult modeling, adult film work, webcamming, stripping, no-sex BDSM or What’s Your Price social-only dates, or having sugar daddies/older wealthier boyfriends for criminalized forms of adult work; or overeating/over-drinking/over-use of or dependence on legal prescriptions prescribed to you/overuse of caffeine.

  • Say what you do, but don’t go into depth about it.

5. What kind of a letter exchange are you into?

Some kinds include:

  • Mentor-style [AA/NA/Re-entry/Writing/Group Facilitation), where you’re offering someone advice, info and support. Write something like “I’m happy to support you around XXX, give advice and connect you with information you might want or need.”

  • Friends/Peers - Communicating mainly about your own different interests, lives, goals, dislikes, whatever. Just providing social connection! Write about your own personal interests, yourself, and ask about them! Write something like “I’m super-glad to connect with you and excited to get to know you better!”

  • Specialized Projects [This can include sending drawings, poetry, or creative writing to each other; collaborating on a ‘zine; whatever]

  • Diary or Journal Entries - just telling them about what you are doing on a daily basis. You can include tales about vacations, trips or even just boredom.

  • More about yourself & questions about the person: Make it a dialogue. Talk about your life, goals, quirks, & interests & ask about theirs!

6. Your Boundaries/Your Capacity:

It’s 100% okay to only write a one-time support letter, or write once/month.

  • One-Time Letter “I’m at [event]. Just wanted to drop you a quick, cheerful note. You rock & I’m rooting for you!”

  • Ongoing correspondence “My financial capacity is really limited, but I’d love to [correspond with you & get to know you better

  • You don’t have to send the person you are writing books or add money to their commissary. But it’s super important to clarify this in your letter! Some ways to phrase this:

“I don’t want to set unclear expectations so I want to let you know up front I am not able to send you money”

“I have a limited financial capacity so I won’t be able to send you money on a regular basis.”

“I am not able to send you commissary funds but I can occasionally purchase a book for you.”


Prisoners love to be able to “see” who they are writing to so they LOVE to get pictures! Just keep in mind that the prisons can still see incoming and outgoing mail so it is being monitored! You can attach a picture to any electronic email at a small additional cost.

  • DO NOT send nudes

  • DO NOT send pornography - this (eye-roll) includes nipples.

  • DO NOT send any images of bombs or firearms. Not even cartoons. Prisons have no sense of humor.

  • DO NOT offer someone a job in something that is criminalized or offer to let someone use your space, rent your space, help someone create a website, learn how to advertise, work with someone, or learn how to engage in sex work or find or sell drugs. We really do not want anyone to be arrested for interstate sex or drug trafficking.

  • Do not forward letters or emails they send you to mail to other people. Especially to other people in prison. THIS IS ILLEGAL. This could get your email denied permanently and could cause your pen pal to get punished and could even result in additional charges against them and against you.

  • They may ask you to get pictures from their facebook pages and send them to them. This is fine. Just be sure the pictures are of them or their family members.

  • They may ask you to contact people that are not in prison. Sadly, this is just a bad idea. We have no way of knowing the relationship status of the person they are trying to get you to contact and keep in mind how YOU feel when random strangers start sending you messages on facebook or other social media.

8. Mental illness and “Awkward” Social skills are common!

Sadly - because of the nature of prison life - folks are disconnected from the rest of the world and often have very little support from the outside. They may be socially awkward from the institutionalization experience. There is also an incredibly high incidence of mental illness in prisons and jails so keep in mind that inappropriate behavior can be a result of all of the above. Gently correct and move on.

9. Prisons no longer provide any kind of “free” items for indigent (very poor) prisoners.

10. Be aware that Pen Pal programs are a “hustle” in prison

We constantly tell our inside pen pals that we do NOT arrange romantic pen pals, they have been known to continue to try and pressure you to send them money for commissary. Please only do what you feel comfortable doing. If they ask for something specific that you do not know how to respond to - suggest they write to SWOP Behind Bars at to make their request.

Ready to get started? Sign up to write to a prisoner using electronic mail today!

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