Serving a jail sentence is never a pleasant experience. However, when it has to be done, there are some things that you can do to make your time in jail more bearable. The following are things that you can do to improve your comfort level while in jail:

Clothing items

While in jail, you’ll be provided with a uniform and some flip-flops or slipper style shoes. They aren’t going to be super clean, comfortable, or particularly warm. In order to deal with this, it is advisable to bring in some clothing items to wear underneath your jail-furnished uniform.

There are only certain items that are allowed inside the jail, and each county’s jail is different in what they allow. Generally, though, you can bring in underwear (usually it must be white and still in the packaging); white t-shirts (again, still in the packaging); and for women, sports bras with no underwires (usually they must be white and still in the packaging.) Some jails will permit you to bring in long underwear, which can be nice in the winter months when the jail can be particularly cold. You should contact the specific jail where you will serve your sentence to find out what their particular rules are with regard to clothing items.

Hair accessories

For women with long hair, it is also advisable for you to wear in a hair tie that does not have metal in it. You won’t have access to your usual styling tools, or even be able to shower as regularly as you might at home, so the ability to pull back your hair will be important.

Money for your commissary account

You’ll want to make sure that you have adequate money available to fund your commissary account while in the jail. Commissary is a service provided by the jail that allows you to purchase needed items such as toiletries and extra food items.

You’ll want a family member or friend to make regular deposits into your commissary account if you are going to have a lengthy jail sentence. In the beginning, you may need a little extra money in your account to buy needed toiletries, such as shampoo, deodorant, comb or brush, toothpaste, and a toothbrush.

You’ll also want to purchase extra food items through the commissary, such as coffee and snacks to eat at times when you’re hungry. Dinner tends to be served earlier in the jail than many of us are accustomed to eating (generally around 4-4:30pm), and you’ll have a long break between dinner and breakfast. Having some snack food to get you through the evening hours will prevent you from going hungry. Also, the jail food can sometimes be less than desirable. Having commissary food probably isn’t going to provide any healthy options, but it may allow you some choices when meals are particularly unappetizing.

There are also condiments available for purchase that can help make the jail food more edible.

In some jails, you can also purchase some limited pharmacy items, such as ibuprofen, cold medication, or tums, that might help cope with any health issues that arise during your sentence. For women, feminine products such as pads or tampons are also generally available for purchase.


One of the things that makes the time in jail most bearable is the ability to have regular contact with your family and friends. You will have the ability to make some limited phone calls while in jail.

Different jails use different services for phone calls being placed from the jail. In most jails, you can purchase phone minutes using one of these services through your commissary account. Especially if you expect a lengthy jail sentence, these calls can get very expensive.

One way to reduce the expense of phone calls is to have your family purchase a phone for the outside that has an out-of-state phone number. Phone calls to numbers outside of the state are more heavily regulated, and the prices per minute tend to be significantly lower.

Some jails now have the ability for family and friends to call and leave voice messages for inmates, as well. There is generally a charge for this service.


Most jails permit visits at least weekly. In order for a family member or friend to visit you, most jails have “visitor lists” that you must complete on your entry into the jail that list all of the people from whom you would like to accept visits.

Sadly, many jails have now gone strictly to video visits, rather than in-person visits. If this is the case, your family and friends can conduct a scheduled video visit electronically.

Each jail has different rules for visiting. You should contact the jail prior to your sentence to discuss the specific rules regarding visits, and make arrangements for your family and friends to visit as often as possible during the course of your sentence.

Work release

Work release is governed by the jail. While the judge who sentences you can and may authorize work release, the jail makes the ultimate decision about whether to grant work release. Each jail has their own individual rules for work release. They will consider factors such as length of employment, proximity of your employer to the jail, availability of transportation, cooperation from your employer, your criminal history, your current conviction, and any history of substance use and/or abuse.

If you are able to obtain work release, you will be released from the jail during your employment hours, and permitted to go straight to work and back. You won’t be permitted to return home or go elsewhere, so you need to plan ahead for work release. You’ll need to stock your vehicle with work clothing and any other supplies you need to be ready for work.

The jail generally charges a fee for participation in work release. Some of that fee must be paid in cash, upfront. It is generally under $200 for the first week. After the first week, the fee will generally be deducted directly from your paycheck. You should bring the cash needed for the first week with you into the jail.

You can also prepare for work release by completing the work release paperwork prior to entering the jail. Ask your attorney if this is possible for the jail where you are expected to serve your sentence, and they can help you with obtaining this paperwork.

If you are granted work release, it makes serving your time in jail much easier. You get to leave the jail for work almost daily, and return to the jail to sleep. While it still isn’t an ideal situation, work release tends to make your time in jail go by much more quickly.

Reading materials

Some jails will permit you to have a limited number of books or magazines delivered to the jail from companies such as Amazon. Again, each jail has their own rules in this regard. Most jails, if they permit books or magazines to be sent in, require that the items be shipped in directly from the company, and not from an individual family member or friend. You should inquire with the jail where you expect to serve your sentence for more information regarding their policy on reading materials.

Having reading materials available will help you to pass the time in jail. And while there may be books available from the jail, having your choice of reading material can help hold your interest and make your time in the jail more productive.

If reading materials are not permitted to be sent in, there is often something available for reading, or reading materials can be purchased from the commissary.

Jail programming

Sometimes there are classes or programs available in the jail. Programs ranging from Alcoholics Anonymous meetings, Cognitive Behavior classes, bible study or religious programs, substance abuse classes are sometimes offered.

In some cases, the programs or classes offered are simply available for your personal benefit. It can be helpful to attend these types of programs, both in order to pass the time, and to work on self-improvement while you are in the jail. Though the programs might not be ideal and as high-quality as you might see outside the jail, participation can be worthwhile.

In other cases, participation in the programs or classes can earn you credit off from your jail sentence. Each jail is different, and you will generally be told when the program is offered to you whether or not credit can be earned toward your sentence for participation in the program.


Sometimes, the jail staff may offer you a position as a jail trustee, especially if you are serving a lengthy sentence and are not participating in work release. This requires you to do a job around the jail or other county property, usually involving manual labor. It can include things like cleaning, yard work, or working in the kitchen.

Generally, the benefits to acting as a jail trustee are staying busy so that the time passes more quickly, and that the jail will likely give you days off from your sentence in exchange for your service.


You should be polite to everyone in the jail, including the other inmates and jail staff. While the jail staff or the other inmates may not be friendly, you should always treat everyone respectfully. Follow the directions of the jail staff carefully.

With other inmates, you should be respectful. However, while it is always good to treat someone with kindness, sharing items in the jail is not recommended. For example, a previous client gave another inmate their calling card number so the inmate could make an emergency call to their family. Shortly thereafter, the client’s minutes were gone, as the inmate shared the calling card number throughout the jail.

It is also recommended that you not take any items offered to you by another inmate. It might be tempting to borrow an item while you wait for your commissary to be delivered, but being indebted to another inmate can result in ugliness later.


If you are on regular medications, it is advisable to contact the jail ahead of time to learn about their procedure for administering the medications while you are in jail.

There are certain medications that will not be given during a jail sentence, including some pain medications and psychotropic medications. You should discuss this with your doctor so that you can be safely weaned from these medications prior to your jail sentence.