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15 of the Best Encouraging Words for Someone in Jail

15 of the Best Encouraging Words for Someone in Jail

Serving jail time is hard on the convict’s family, but it’s even harder on the convict. There’s no college course on crafting encouraging words for someone in jail, but they are still very necessary.

If you know someone who is in jail, some encouraging words could help the person you know to keep his/her hopes up. You can learn how to craft encouraging words for someone in jail with our free templates below.


Five encouraging words for someone in jail: When someone is in for a short time (one month to one year)


01“Dear Maggie, I am writing to say that I can’t wait for you to get out of jail.
There is so much waiting for you outside – great food, wonderful parties, your family. I can’t wait to share all of these things with you.
I don’t want you to fret too much about the past. I don’t intend to dwell on that either.
PS: I am waiting for you with open arms.”


This phrase is encouraging for any convict because it looks forward and into the future positively. It presents you as a non-judgmental individual who is more focused on what can happen next.


woman with tied hands closed eyes messy hair
Photo by Engin Akyurt under pexels license


02“Louie, you are one of the strongest people I know, and you have always known how to find the simple joys in any situation.
I am counting on you to delve into yourself to find that special ability for your current situation, and I hope that it can help you to stay afloat for as long as it takes.
Please stay strong, man. We love you.”


One of the best ways to encourage someone is by highlighting his/her strongest points. This phrase does just that, and it is generic enough to work for anyone.


03“Marty, son, whatever you are feeling or thinking, I want you to remember that all difficult times come to an end.
Your current situation is one of those difficult times, and it will end too. I’ve been through some difficult times myself, and that thought always got me through. I found a way to remain sane and sound.”


This is a good phrase to use because it positions you as someone who has been through some tough times too; your words of encouragement will likely land with more gravitas because of this position.


silhouette of a man in window

Photo by Donald Tong under pexels license


04“Timmy, how’s it hanging?
Just so you know, I am on your side, and I am never going to judge you for what happened.
As you get through your sentence, I hope you don’t worry too much about what will happen next because the future is not yours to control.
Saying that, I want you to remember that there is an end in sight, and it’s not over for you yet.”


This phrase is perfect for encouragement, as it’s filled with positive vibes and hopeful messages. It’s also rather flexible in a generic way, so it can be tweaked to work for any message to a convict.


05“Dear Judy, I hope you are staying strong. I am writing to tell you that I love you, and things will get better.
I am also confident that, with the lawyer you have (and I have spoken to him), your appeal will be successful. I’m sure that you will be out in no time.
Sending lots of love, dear.”


Sometimes, a convict needs a little encouragement from the outside world; this message is full of hope about the situation, love, and support.


woman wearing black blouse with white polka dots working laptop

Photo by Mateus Campos Felipe on unsplash


Five encouraging words for someone in jail: When someone is in for a long time (two years to 10+ years)


06“Hey sis, I know that life in there isn’t the greatest, but I want you to know that I am always thinking of you. I will always be here for you.
Also, I recently learned that many folks in your exact situation have been released halfway through the sentence for good behavior before, and that you can get it too if you maintain good behavior.
I hope this information can make you feel better, at least for a while. Stay safe, sis.”


This phrase is good because it shows a way out for the convict, and it provides another solution that could work for him/her. This can be very encouraging for the convict to hear.



07“Dear David, last night, we put up the Christmas decorations, and we all missed you. We aren’t about to lose hope, honey.
I teach the kids about their daddy every day, about how he is a good man, and most importantly, how he will be back soon.
So, I don’t want you to worry about them or that they’ll forget you. Stay strong for us, honey. We love you.”


This phrase works well for encouragement because it is filled with updates about life. The message is one of love and hope in one perfect statement.


woman and a girl sitting on the sofa talking christmas tree
Photo by cottonbro under pexels license


08“Nora, darling, these days, I am filled with so much hope at the end of each day. Every day’s end means that I am one day closer to seeing you again and holding you again.
It’s lonely out here, but the thought of a future with you comforts me. No matter how long it takes, I know that you will be back in my arms.
Good times are coming, Nora, and we shall be together again soon.”


Any phrase that tries to paint the distant future as one that is filled with love and freedom is bound to work wonders. It is the perfect attempts at providing encouragement to a convict.


09“Dear Patrick, I hope you are getting by okay. I know that you worry about our wellbeing, so I just want you to know that we are doing fine.
I have found ways to cut costs here and there, and I recently received a small raise. So far, we’re staying afloat, and we’re okay.
Also, the kids and I can’t wait to see you next month.”


Since you’re hinting that you are starting to balance the family’s financial wellbeing, and things are looking up, this phrase can really help to encourage the convict.


baby putting the sunglasses on her mother

Photo by Katie E under pexels license


10“Louis, I hope you are doing well. I went to see your parents. I go every two weeks to bring them some supplies, and they are doing well.
Your Ma says hello, and she is praying for you. Your Dad has recently recovered from a bad cold too.
I will be back to see you next week. Stay positive.”


With this phrase, you can give positive updates on his/her loved ones, and you can promise to visit soon, both of which work wonderfully in boosting the convict’s morale.


man standing while hanging his arms on the fence

Photo by Pablo Padilla on unsplash


Five encouraging words for someone in jail: When someone is jailed for life


11“I need you to know that God sees you and hears your prayers.
It’s true that God always has the best plans for you, and even though this feels like the end of your life, I want you to know that God’s plan for you isn’t over.
He knows that we are sinners, and he listens when we repent. God loves us all equally, and He never gives up on us.”


This phrase works wonderfully, especially if the convict believes in God because it highlights that his/her life is still worth living. It demonstrates that there is a higher power in control.


man in black shirt wearing cap inside the jail

Photo by Damir Spanic on unsplash


12“Peter, I know you must be convinced that a life sentence is the end of the road for you. I need you to know that even with a life sentence, there is always some hope for an early release.
Pardons are still possible, and government policies can change. There is always an opening for change that could come up. As you wait for yours, I will be here for you.”


This phrase is good to use because it is hinting kindly and giving examples of ways that the convict could get out before the end of his/her life. The message says that there is still a way out, which can be very encouraging for a convict with a life sentence.



13“Marla, I know that ever since the sentencing, you feel ashamed and embarrassed.
I would never pretend to know how you feel, but I just want you to know that to us – your family, friends, and your community – you are a good person who has faced some challenges. We understand that because we all face challenges.
Unsurprisingly, the love and support for you over here is pretty overwhelming.
Stay hopeful, sweetheart.”


This phrase is good to use because it highlights the love and support that the convict has, which is encouraging because many convicts lose all support from the outside world over time.


family gathering for a group hug
Photo by August de Richelieu under pexels license


14“I cannot pretend to understand what you are going through right now, but all I want you to know is that nothing has changed for me.
With or without a life sentence, I still love you wholeheartedly. I don’t want you to ever doubt that. I’ll be waiting for you, even if it means waiting forever.”


Some convicts with a life sentence will worry about losing people’s affection and being forgotten. This phrase reminds the convict that they need not worry about all of that.


15“Your current situation is unfortunate, but I implore you not to give up.
I am already working with a lawyer to work on an appeal in the sixth circuit for you, and while I can’t promise anything, there’s appeals like yours that have been successful.
We’ll keep fighting until something gives, and a solution is found.”


There’s nothing more powerful and encouraging for a convict than knowing that he/she has someone fighting for his/her cause, despite the bleak circumstances. This phrase provides positivity and hope for the convict.


man in maroon shirt sitting near metal fence

Photo by Alex Radelich on unsplash



The best kind of encouraging words for someone in jail are those that are filled with hope, kindness, and faith in the convict, regardless of the jail sentence.
Coming up with encouraging words for someone in jail is not hard when you include emotion in your message.
However, if you feel that you don’t have a knack for it, then these free templates above can help you.