Helping Your Incarcerated Loved One Navigate Technology Before Reentry

Preparing for reentry means more than finding housing or employment—it’s also about helping your loved one adapt to a world transformed by technology. Smartphones, email, online banking, and even basic tasks like self-checkout can feel overwhelming for someone who’s been disconnected from these tools for years.

As their support system, you can guide them in mastering the basics, even if your communication is limited to phone calls or letters. Here’s how to empower your loved one to navigate technology confidently and effectively, including book resources to make the process easier.

1. Start With the Basics

Introduce your loved one to essential tools they’ll need for daily life.

Smartphones: Explain how to make calls, send texts, and use apps.
Internet Browsing: Teach them how to search for information, access websites, and use email.
Banking Basics: Break down how to check balances, make transfers, or pay bills using online tools.

💡 How to Teach From a Distance: Use letters to describe step-by-step instructions. Include drawings or diagrams if needed, like how to navigate a phone screen or use a search engine. During phone calls, role-play scenarios like setting up an email account or searching for a job online.

📚 Book Resource: “Computers Made Easy: From Dummy to Geek“ by James Bernstein—A beginner-friendly guide to basic computer and internet skills.

2. Discuss Online Safety and Privacy

Technology is powerful, but it also comes with risks. Teach your loved one how to protect themselves online:

Passwords: Explain how to create strong passwords and why they shouldn’t share them.
Scams and Phishing: Warn them about fraudulent emails, links, and messages asking for personal information.
Social Media: Guide them on setting up accounts with privacy controls and avoiding oversharing.

💡 How to Teach From a Distance: Write out common red flags of scams or phishing attempts. During calls, quiz them on scenarios, like recognizing a suspicious email or protecting their personal data.

📚 Book Resource: “Cybersecurity for Beginners“ by Michael Patel—An easy-to-read guide on staying safe online.

3. Focus on Practical Tools for Reentry

Help your loved one learn technology that will ease their transition back into the world.

Job Applications: Explain how to fill out online forms, attach résumés, and email potential employers.
Public Transit Apps: Teach them how to use apps for bus schedules or GPS.
Budgeting Tools: Show them how apps like Mint or EveryDollar can help manage finances.
Health Resources: Explain how to book doctor’s appointments or use patient portals.

💡 How to Teach From a Distance: Write sample job application templates in letters, highlighting where they’d input their details. Role-play submitting a job application over the phone, discussing each step.

📚 Book Resource: “Digital Literacy: A Primer On Media, Identity, and the Evolution of Technology” by Susan Wiesinger—A comprehensive guide to practical digital skills.

4. Role-Play Real-World Scenarios

Building confidence comes from practice. Help them prepare for common tech-based tasks.

Using Self-Checkout: Describe how to scan items, pay, and get a receipt.
Filling Out Forms: Walk them through a simple online form step by step.
Email Etiquette: Teach them how to write professional emails, attach documents, and respond to messages.

💡 How to Teach From a Distance: Include practice forms or write mock scenarios in your letters. During calls, talk through situations and let them explain how they’d respond.

📚 Book Resource: “Internet for Dummies“ by John Levine—Great for beginners of any age.

5. Encourage a Growth Mindset

Learning new skills can be frustrating, especially with limited access to technology. Encourage them to stay positive.

Normalize Mistakes: Remind them it’s okay to stumble while learning.
Celebrate Wins: Acknowledge progress, like learning how to log into an email account.
Take It Slow: Introduce one tool at a time to avoid overwhelming them.

💡 How to Teach From a Distance: Use letters to offer encouragement. Share stories about how you learned technology or overcame struggles with patience and persistence.

📚 Book Resource: “Mindset: The New Psychology of Success“ by Carol S. Dweck—A book about embracing challenges and building resilience.

6. Provide Resources for Independent Learning

Equip your loved one with tools to continue learning after release.

Libraries: Many offer free computer classes and internet access.
Community Programs: Look for reentry organizations that provide tech training.
Online Tutorials: Recommend beginner-friendly tutorials on YouTube for post-release use.

💡 How to Teach From a Distance: Create a resource list in a letter that they can refer to once they’re released.

📚 Book Resource: “Teach Yourself VISUALLY…“ (series) by Paul McFedries—A visual guide perfect for beginners.

7. Stay Connected and Patient

Helping your loved one learn technology requires patience and encouragement.

Follow Up: Check on their progress during calls or visits.
Be Their Cheerleader: Remind them how far they’ve come and the opportunities these skills will unlock.

💡 How to Teach From a Distance: Share stories of how learning technology can make life easier, like reconnecting with family or applying for their dream job.

Final Thoughts: Empowering Through Technology

By teaching your loved one to navigate technology, you’re not just helping them adapt to the modern world—you’re empowering them to rebuild their independence and confidence.

💙 “Every skill they learn is a step closer to a brighter future.”

For more tips and support, check out Chapters and Chains for resources and advice tailored to your journey.

What technology tips have worked for you and your loved one? Share your experiences in the comments—we’d love to hear your insights!