What a Letter Looks Like
Every month, inmates receive a thoughtfully written letter prepared in a warm handwritten-style format, filled with Scripture, hope, and encouragement.
Every month, a warm, handwritten-style letter is mailed with hope, Scripture, and encouragement - reminding them that even behind bars, they are still seen, loved, and prayed for.
If you have a loved one behind bars, you already carry more than most people understand. You're not alone in feeling this way:
EncourageMonthly shows up for them - every single month - so you never have to wonder if they feel loved.
Choose your plan on EncourageMonthly.com, then complete one short guided survey (your details, your loved one’s mailing address, and checkout) on the subscription page. Takes less than a few minutes.
Pastor James Oliver - a local pastor and jail chaplain with nearly a decade of ministry experience behind bars - personally writes and reviews each monthly message. Because his handwriting is honestly difficult to read, letters are prepared in a warm handwritten-style format so they stay personal, clear, and encouraging.
Each month, the letter is mailed to your loved one. Some facilities may scan letters and deliver them digitally, but the message of hope still reaches them. We also send you a digital copy so you can see what was sent and talk with them about it if you'd like.
Consistent, pastoral encouragement builds over time. Month after Month, your loved one knows someone is standing with them.
Every month, inmates receive a thoughtfully written letter prepared in a warm handwritten-style format, filled with Scripture, hope, and encouragement.
A Word from Our Founder
For nearly a decade, I have served as a local jail chaplain and pastor, sitting with men and women who often wonder if anyone on the outside still remembers them. I have seen firsthand what steady encouragement can do for someone who feels forgotten.
Every monthly letter is personally written and reviewed by me, then prepared in a warm handwritten-style format so it remains clear, readable, and personal. From time to time, I may add a handwritten touch, but the heart of this ministry is not fancy handwriting. It is faithful encouragement that keeps showing up.
EncourageMonthly exists because consistency matters. Not one card at Christmas. Not a letter you meant to write but never finished. A faithful, monthly reminder that God is present, their life still matters, and their family has not given up on them.
"I was in prison and you came to me."
- Matthew 25:36 · The Words of Jesus
No hidden fees. Cancel anytime. Every plan includes monthly letters of hope, Scripture, and encouragement prepared with care.
Monthly Commitment
(For Monthly Encouragement)
$7.99
per month · billed monthly
Annual Commitment
$84
Only $7/month when billed annually · Save over $11/year
✦ Secure checkout powered by Stripe · All major cards accepted · Cancel anytime
Thank you Pastor James for writing me and encouraging me. I'm struggling here right now. I'm trying to remain hopeful and read my Bible. Your letter helped me get focused back on Jesus again.
Letter recipient
Bro! I'm glad you wrote back! I miss all of the people back at the jail. I have parole soon. Keep praying for me and I hope to see you soon when I get out! Thanks for sending your sermon. I'd love to get more when you have time.
Letter recipient
Keep praying pastor. I have been in a lot of pain lately. I went to medical, but there's not a lot they can do to help right now. I'm in constant pain. I love getting these letters from you.
Letter recipient
Will the prison actually deliver the letters?
Most correctional facilities accept incoming mail. We mail standard first-class letters that comply with general mail regulations. If your facility has specific requirements, such as no staples, white envelopes only, or other mailing guidelines, please let us know and we will do our best to accommodate those guidelines.
Are the letters religious? What if my loved one isn't a Christian?
Our letters are faith-based and rooted in Scripture. They are written with warmth, compassion, and respect - never condemnatory. Many recipients who are not practicing Christians have found them uplifting and hopeful. However, if faith-based content isn't a fit, this service may not be the right one.
Are these letters actually handwritten?
Each monthly letter is personally written and reviewed by Pastor James Oliver, then prepared in a warm handwritten-style format so it is clear, readable, and personal. Pastor James may occasionally add handwritten touches, but the regular Monthly letters are not promised to be individually handwritten by hand.
Is every letter completely unique per subscriber?
No. Each month, Pastor James writes one encouragement letter centered around Scripture, hope, and real-life encouragement for those who are incarcerated. Subscribers receive that month's letter, prepared with care and mailed to their loved one.
Can I cancel at any time?
Yes. Monthly subscribers can cancel anytime before their next billing date with no penalty. Annual subscribers are billed for the full year upfront, but we are happy to discuss any concerns - just reach out.
How do I provide the inmate's mailing address?
On the monthly or annual subscription page, you’ll complete one guided survey. It asks for your details, your loved one’s first and last name, inmate number, birthdate if you know it, facility name, and the mailing address the institution uses for inmate mail, then secure checkout for the plan on that page.
Hope delivered monthly. Pastor-written encouragement that keeps showing up. For as little as $7 a month with an annual subscription.