You can connect with inmates online through a service like InmateDB, which lets you send messages, photos, and letters from your phone or computer. It works for facilities in the U.S. and Canada, and the inmate gets your message on a secure tablet. Here’s how to do it, what to expect, and what usually trips people up the first time.

Step 1: Check if the facility allows online messaging

Most facilities now have tablets, but not every jail or prison uses the same system. Some only allow email through their own vendor, others allow third-party apps like InmateDB. Before you sign up, call the facility or check their website to see if they permit outside messaging services. You don’t want to pay for a month and then find out your loved one’s facility blocks it. If you’re not sure, ask the inmate or someone who’s been through it. The front desk staff might not know, but the inmate will—they see what apps are on their tablet.

Step 2: Set up your account and add the inmate

Once you know it’s allowed, go to the service’s site and create an account. With InmateDB, you’ll enter your name, email, and payment info. Then you add the inmate by their name and ID number. You’ll also pick their facility from a list. If you don’t see the facility, don’t assume it’s not supported—contact support first. Sometimes the facility goes by a different name or is listed under the county.

When you add an inmate, you’ll start a 5-day free trial. That’s enough time to send a few messages, see if they come through, and get a reply. You’ll need to enter payment details even for the trial, so be ready for that. If you cancel before the trial ends, you won’t be charged. The monthly cost is $19.99 per inmate, so if you have more than one family member inside, you’ll pay that for each.

Step 3: Send your first message (and what to write)

You can type a message right in the app. Keep it simple at first—a few lines about what’s going on at home, a question, or a memory. The first message often feels weird because you’re not sure what to say. That’s normal. You don’t need to write a letter. Just say hi and tell them you’re thinking of them. You can also attach a photo, but check the size limits and make sure the photo is appropriate. No nudity, no gang signs, nothing that could be considered contraband. If you’re not sure about a photo, don’t send it.

When you hit send, the message doesn’t go straight to the inmate. It goes to a review queue. Most messages are reviewed within 24 hours, but it can take longer on weekends or holidays. If a message gets flagged for some reason, you’ll get a notice. You can’t appeal it, but you can rephrase and try again.

Step 4: Understand how the inmate sees your message

On their end, the inmate gets a notification on their tablet. They’ll see your message in a simple chat-style interface. They can read it and reply, but they can’t see your message instantly. There’s always a delay. Also, inmates have limited time on the tablet, so they might not reply right away. They might read it during their free time and then write back later. That’s not a sign they don’t care—it’s just how it works.

InmateDB also gives inmates access to AI chat, email, news, lessons, trivia, and a private journal. So even if you’re not messaging every day, the tablet is a way for them to stay occupied and connect with the outside world. If you want to send a longer letter, you can type it in the app and it goes through the same system. It’s not the same as a handwritten letter, but it gets there faster and doesn’t get lost.

Step 5: Know the real timeline

Here’s what most families don’t expect: the first few messages might take a couple of days to get a reply. The inmate might not check their messages every day, and the review process adds time. If you sent a message on a Friday, it might not get reviewed until Monday. So don’t panic if you don’t hear back within a day. If it’s been a week and no reply, that’s when you should follow up—either with the facility or by calling customer support for the service.

Another thing: the inmate might not be good at typing. Many people inside haven’t used a keyboard in years. So their replies might be short, misspelled, or take a while. That’s okay. The point is to stay in touch, not to have a perfectly typed conversation.

Step 6: Handle the money part honestly

Cost is the thing that makes most families hesitate. $19.99 a month adds up—that’s about $240 a year. But compare that to phone calls, which often cost $0.25 to $0.50 per minute. A 15-minute call a few times a week can easily run $30 to $60 a month. So online messaging can be cheaper, especially if you’d otherwise be making long-distance calls. It also lets you send photos, which you can’t do over the phone.

If money is tight, you can use the free trial for five days and then cancel, and just use the service during that window. Or you can set a budget: only send messages on weekends, or share an account with another family member. The key is to be honest with yourself about what you can afford. Don’t go into debt to send messages. The inmate would rather get a message once a week than have you stress about the bill.

Step 7: Expect a learning curve for everyone

The first time you use the service, you might fumble around. You might send a photo that’s too large, or type a message that gets rejected because it mentions something prohibited. That’s normal. You’ll get the hang of it. The inmate is learning too—they might not know how to open a photo or how to scroll through messages. Be patient. If something doesn’t work, try again. If the message still doesn’t go through, contact support. They’re used to helping families like you.

One common mistake: assuming that because you sent a message, the inmate got it. They might not have checked their tablet yet, or the facility might have had a lockdown and tablets were taken away. If you don’t get a reply, don’t assume the worst. Send a follow-up after a few days. If you still hear nothing, call the facility and ask if the inmate has access to their tablet.

Where to start

If you’re ready to try it, start with the free trial on InmateDB. Create an account, add your loved one, and send a short message. Don’t overthink the first message—just let them know you’re there. The trial gives you five days to see how it works. If it’s not for you, cancel before the trial ends and you won’t be charged. If it works, you’ll have a direct line to someone you miss.

No system is perfect. There will be delays, glitches, and moments of frustration. But when you see a reply from your person, it makes it worth it. That connection is the whole point. So take the first step, and see how it goes.