What to Take Into Prison: The First Night Checklist From Someone Who Has Done It

By Daniel Hockey, former Category B, C and D prisoner in England and Wales and author of Prison Survival Guide. Published: March 10, 2026.

When the van doors opened and I walked into reception for the first time at HMP Pentonville, I genuinely had no idea what I was allowed to keep. Nobody tells you. Your solicitor doesn’t mention it. The court doesn’t prepare you for it. I lost a watch that had belonged to my father—not because it was banned, but because I hadn’t been told it would be logged and stored in the property system. That single oversight taught me more about the first night in prison than any official briefing ever could. Now, after serving time in Category B, C and D prisons, I’ve learned exactly what to take into prison and what to leave behind. This guide comes from lived experience, not theory.

Why Your First Night in Prison Matters More Than You Think

The first night sets the tone for everything that comes next. I remember standing in reception at HMP Pentonville, my hands shaking, still in the clothes I’d worn to court. Around me were officers checking paperwork, searching bags, weighing items on scales. A man in front of me was being told his trainers didn’t meet the requirements. Another had all his letters confiscated because they contained certain information. I was watching chaos that could have been prevented with five minutes of proper preparation.

Your first night in prison is controlled by reception procedures. These are strict, they’re standardised, and they apply to everyone regardless of what prison category you’re entering. Whether you’re going to a Cat D open prison or a Cat A dispersal, the rules about what to take into prison are broadly consistent, though there are variations I’ll cover later. The key thing is this: if you arrive unprepared, you lose things. Items get confiscated. You start your sentence already frustrated. And in prison, that frustration can affect how other inmates see you from day one.

I learned this by getting it wrong. When I was taken into custody after sentencing, I had a £4,000 watch, three pairs of expensive trainers, and a Louis Vuitton bag full of personal items. By the time I got processed into the wing, I had none of those things. They were “stored” in the property system—which meant I wouldn’t see them again for the entire sentence. The watch? My father’s watch. I could have brought it, had I known the rules about what to take into prison. Instead, I’d made assumptions.

What to Take Into Prison: The Essential Checklist

Let me be clear: you don’t actually choose what to take into prison. The prison does. You can bring certain items, but they will be screened, checked, and often logged into the property system. However, knowing what to take into prison prevents rejection at reception. Here’s the list I wish someone had given me.

This is what to take into prison based on years of experience. But there’s a crucial thing you need to understand: each prison has variations on these rules. The list above works for nearly every Category B, C and D establishment, but it’s not exhaustive. Some prisons are stricter than others. HMP Brixton, for example, is stricter about clothing brands than HMP Downview. These differences matter.

Clothing Allowances and What’s Actually Permitted

Clothing is where most people get it wrong when they figure out what to take into prison. You’re allowed to wear your own clothes in all English prisons, unlike some other countries where you wear a prison uniform. However—and this is a big however—there are rules about what to take into prison in terms of clothing.

In my first week at HMP Pentonville, I watched an officer tell a lad he couldn’t keep a Burberry hoodie. Not because it was banned outright, but because distinctive branded clothing can cause issues—it marks you as having money, it creates hierarchies in the prison, and officers prefer to keep visible status items to a minimum. What to take into prison for clothing should be neutral: plain, clean, undamaged clothes without large logos or brand names visible.

Here are the practical rules about clothing when deciding what to take into prison:

• Trainers: You can bring one pair, but they need to be clean and practical. Expensive designer trainers stand out. I recommend plain white, black, or grey. No Air Jordans. No Yeezys. They’ll either be taken off you, or you’ll spend your sentence worried about them.
• Jeans: One pair is fine. Make sure they fit properly and don’t have rips or excessive distressing. Avoid distressed jeans—officers sometimes interpret them as damaged goods that shouldn’t be in prison.
• T-shirts: Bring plain ones. No band logos, no offensive slogans, no sports team shirts. Plain means navy, grey, black, or white. That’s it.
• Underwear: New is better. White is safest. Bring two pairs at minimum, though the prison will provide underwear if you need it.
• Footwear: One pair of proper shoes (black leather, formal) and one pair of slippers. The formal shoes are for visits, adjudications, or appointments with the Governing Governor. Get them right.
• Hoodies and jumpers: One is fine. Navy or grey is safer than black. Avoid expensive-looking clothing.
• Belts: You can take one plain leather belt, but it must have a simple buckle. No statement belts. Belts can be used as weapons, so anything flashy gets confiscated.
• Hats: You can bring one hat, but it won’t be allowed to be worn indoors. It’s just for outside.

The key principle: when you’re choosing what to take into prison for clothing, imagine explaining it to a security officer. If you wouldn’t feel comfortable explaining it, don’t bring it.

Toiletries: What You Can Bring and What the Prison Provides

Toiletries are a major question when figuring out what to take into prison. The short answer is: you can bring basic ones, but the prison will provide most of them. However, there’s a difference between what you can bring and what’s actually useful to bring.

At HMP Downview, reception gave me a state-issue soap, state-issue toothpaste, and state-issue deodorant. They were functional. They weren’t pleasant. After three weeks, I understood why people asked their visitors to bring toiletries. What to take into prison in terms of toiletries should therefore include:

What to take into prison should not include alcohol-based products, flammable items, or anything in large quantities. Reception staff will check the size of containers. They’ll confiscate anything over certain limits—typically 250ml for liquids, though this varies. I once saw a man have to throw away a full-size bottle of shampoo because it exceeded the limit. He’d brought it thinking he was being practical. It was wasteful.

One thing I learned: bring a small towel. Not necessary, but useful. Prison provides towels, but they’re rough and thin. A small microfiber towel from your house takes up almost no space and makes a genuine difference to daily life.

Money at Reception: How Much You Can Have

This catches people out constantly. When deciding what to take into prison, money is something you actually can bring—but there are limits, and the process is specific.

You’re allowed to bring up to £75 in cash to reception. Not notes. Cash. Coins count. However, here’s what you need to know that nobody explains properly:

• The £75 limit is strictly enforced. If you arrive with £100, they take £75 and return £25 to whoever brought you, or it goes into a sealed envelope to be sent back to a nominated address. You don’t get to keep all of it.
• That £75 is logged into your property account. It doesn’t stay as cash. It’s converted to spends (the prison’s internal currency system) and you access it through the canteen order system. You’ll use it to buy extra toiletries, snacks, phone credit, and other items.
• You can’t supplement this with visits. Visitors can’t hand you cash. They can only add money to your account through the official visiting system if the prison allows it, which varies by establishment.
• Larger amounts can be sent via postal order. If family wants to add money to your account after you’ve entered, they use postal orders, not cash. These go through the mail system and take time to process.

What to take into prison in terms of money: realistically, bring £50-£75 in small coins and notes. Have it ready in a clear plastic bag or envelope. Don’t hide it. The moment you’re in reception, officers will find it during the search anyway. Being upfront about what to take into prison regarding money saves complications.

I made a mistake here too. I arrived with £200 thinking I’d be clever about hiding some of it. I wasn’t clever. I was searched. They found it all. I lost £125 and created an instant reputation as someone trying to beat the system. Not the reputation you want on day one.

Essential Documents You Should Bring

Documentation is one of the most important things to include when planning what to take into prison. I’m not just talking about the obvious legal documents—though those matter. I mean the specific documents that make your life immediately easier once you’re inside.

Why does documentation matter this much? Because the prison system runs on paperwork, and if you don’t have it, you’ll spend weeks chasing it down. Your sentence paperwork needs to be there so you can verify your sentence length, your eligibility dates, and your release date. If there’s a discrepancy—and sometimes there is—you need to spot it immediately, not three months in.

When I arrived at HMP Brixton, a man in my cell didn’t have his sentence paperwork. He’d left it with his brief. Took three weeks to get copies. Three weeks of uncertainty about his release date. That’s completely avoidable. What to take into prison should always include copies of key documents—not originals necessarily, but copies. Originals go in property storage. Copies stay with you.

Medical documentation is critical too. If you take medication and don’t bring the prescription or evidence of the prescription, reception won’t know what dose you’re on. The prison GP will need to verify it. It delays your first dose. Bring medical evidence of anything you’re claiming—it saves days of bureaucratic waiting.

Electronics and Your Phone: What Actually Happens

This is where I need to be absolutely clear, because people arrive with illusions about what to take into prison.

You cannot bring electronics into prison. Full stop. No phones. No tablets. No laptops. No smartwatches. No headphones. No USB chargers. Nothing that could potentially transmit data or information.

What happens if you try? Reception staff will find it during the search. If they think you were deliberately trying to smuggle it in, you’ll be charged with an additional offence. Trying to bring prohibited items into prison is a separate crime under the Serious Crime Act 2015. You’re already in prison. You don’t want another charge.

I watched a lad at HMP Pentonville get an additional 6 months added to his sentence because he arrived in reception with a phone he “forgot” about. That “forgotten” phone became “attempted introduction of contraband.” His sentence went from 18 months to 2 years. His family didn’t visit him for two months because he hadn’t been able to ring them to explain.

The reality of phones in prison: they’re everywhere, yes. Inmates get them in. But that’s through visitors, through corrupt officers (rare but it happens), through other means. You will not successfully bring one in through reception. The search is too thorough. The technology detects metals. Officers search you body cavity if they have reason to suspect it. Do not try.

What you should do with your phone before arriving at prison:

• Back up important phone numbers and email addresses to paper. Write them down. You won’t have access to your contacts list.
• Set up a trusted person to manage your phone temporarily—a family member who can keep it safe while you’re inside. Don’t assume you’ll get it back immediately on release; it might be in storage.
• Cancel any subscriptions before you arrive. Phone contracts will still charge you if you don’t cancel them.
• Let your important contacts know you’ll be unavailable. They need to send mail if they want to communicate.
• If you have a smart home device, disable it or have someone manage it. You can’t control it from prison.

What to take into prison regarding communication: a pen and paper. That’s it. Everything else goes through the mail or visits.

What Happens to Your Property at Reception: How the System Works

This is where I lost my father’s watch. Not because it was confiscated—because I didn’t understand the property system.

When you arrive at reception, every item you bring goes through a process. Here’s exactly how it works, from my experience and what I’ve seen in multiple prisons:

1. Initial search: You’re taken into a private room. You remove your outer clothing. Officers search you and your belongings. Phones, weapons, drugs—anything prohibited is seized and reported. You’ll be charged separately if applicable.
2. Detailed inventory: Every item is listed. Clothing, toiletries, documents, money—all of it. This list is printed out. You should read it carefully. If it says “one pair black trainers, worn, Nike” when you actually brought “one pair white trainers, new, Adidas,” you need to correct it immediately.
3. Separation of items: Property is split into categories. What you keep on the wing (personal clothing, toiletries, documents, medications) versus what gets stored. Expensive items, branded clothing, excess cash—these typically go into storage.
4. Storage logging: Stored items are placed in a property bag with a unique number. This number is your reference. You can request to send items home, access them for visits, or retrieve them on release. But you have to know the system to do it.
5. Wing supply: You’re given the items you’re allowed to keep immediately—a small amount of toiletries, underwear, documents. The rest is stored.

Here’s what I didn’t understand: my father’s watch wasn’t banned. It just went straight into storage, and nobody explained how to request it for visits or how the system worked. I thought I’d lost it. I hadn’t. It was just logged away, and I had no process to get it back. For three years I had no idea where it was. (I got it back, eventually, on release.)

The property system differs slightly by prison category and governor’s discretion, but the principle is the same everywhere. What to take into prison needs to account for this: bring one good watch, not three. Bring one pair of good trainers, not five. Anything excess will be stored, and managing stored property is a bureaucratic nightmare.

You can request property be sent home. You can arrange for items to be brought to visits. But it requires a form, a request to the property office, and processing time. In some prisons this takes days. In others it takes weeks. Plan accordingly.

What NOT to Take Into Prison: Banned Items and Consequences

This is where legal matters and safety collide. The Prisons Act 1952 and the Prison Rules 1999 outline what’s prohibited. But there are also operational items that are banned by HMP policy. Knowing what NOT to take into prison is as important as knowing what to bring.

The consequences for bringing prohibited items range from loss of the items to additional criminal charges. You could be prosecuted. You could get extra time added to your sentence. You could be moved to a more restrictive prison category. None of this is worth it.

I’ve seen someone get added charges for a single cigarette lighter. I’ve seen someone lose three months of privileges for a sealed packet of tobacco. Prison security is not a game, and what to take into prison should reflect that this is a high-security environment where the rules aren’t negotiable.

What to Leave at Home and Why

This is about practicality as much as rules. Some things aren’t banned, but they’re pointless to bring because you’ll lose them, they’ll cause problems, or they’ll be seized anyway.

• Valuables: Wedding rings are allowed if you normally wear them. But keep expensive jewellery at home. The temptation for theft inside is high, and insurance doesn’t cover items inside prison. I knew someone who brought a £3,000 engagement ring. It was stolen within a month. Never recovered.
• Multiple pairs of trainers: You can bring one. One. Not two, not three. Anything more looks like you’re planning to trade them, and that raises red flags. Wear one pair, leave the rest at home.
• Expensive clothing: Designer labels create targets. I came in with a Burberry jumper. It was confiscated immediately as “distinctive branded clothing.” I never saw it again. Bring plain stuff. Seriously.
• Books with loose pages: Prison doesn’t allow books that can be easily dismantled. Hardback books are fine. Paperbacks are fine if they’re intact. But don’t bring books held together with tape or with missing pages.
• Letters from previous relationships: This is personal advice—but letters from exes, or suggestive material, will cause you complications inside. Cell mates will find it. Jokes will be made. Gossip spreads. Leave it at home.
• Your freedom clothes: Don’t wear your best clothes on the day you’re arrested. Wear something neutral. Whatever you’re wearing when you’re taken into custody becomes evidence, and you might not see it again for months. I’ve known people who missed funerals because their court outfit was still “in evidence storage.”
• Anything connected to your crime: Literally anything. A notepad. A jacket. A phone that might have evidence on it. The temptation is to bring it to explain your side, but it becomes evidence against you. Your solicitor will advise on this specifically, but assume anything connected to your case stays with your brief, not in your cell.
• Items with sentimental value you can’t afford to lose: My father’s watch taught me this. If you can’t afford to lose it—emotionally, not financially—don’t bring it. Leave it at home with family. Bring a copy of a photo instead.

Preparing Someone Else for Prison: Advice for Families

If you’re reading this because someone you love is about to enter prison, this section is for you. You’ll be asking what to take into prison, but you might be asking it because you need to help prepare them. Here’s what families need to do.

1. Get them to the reception appointment prepared. They should arrive on time, clean, in neutral clothes. Don’t be late. Late arrivals are noted and affect your first-night experience.
2. Help them make a written list of emergency numbers. They won’t have access to your phone. Write down your number, your address, your workplace number, any other key contacts. They’ll need this for the emergency contact form. Make sure it’s legible.
3. Gather medical information before they go in. If they take medication, get a letter from the GP confirming the medication and dose. If they have allergies, write them down. This saves the prison from guessing and potentially harming them with incorrect treatment.
4. Make copies of key documents. Birth certificate, marriage certificate, children’s birth certificates if applicable. House deeds if they’re relevant to their case. Prison likes documentation. Have it ready.
5. Don’t let them arrive with contraband. I mean it. Make sure they understand no phones, no drugs, no weapons. If they try to sneak something in and it’s found, you’ve both created a problem. Be the voice of reason here.
6. Be prepared to visit within the first few weeks. The first visit is crucial. It’s when they’ll have questions about property, about the system, about things that don’t make sense. You can bring £20 in cash for their spends account during the visit if the prison allows it (this varies by establishment). They’ll be grateful to see you.
7. Expect to post them things. Toiletries run out. They’ll request specific items. Set up a system for sending mail and packages. Small items—writing paper, books, postcards—are lifelines in the early weeks.
8. Don’t be offended if their first letters are short. Everything is strange. Their handwriting might be shakier. They’ll be adjusting. This is normal. Just keep communicating.

The best thing a family can do is prepare the person going in with complete information. Download the prison’s information pack (available on gov.uk for most establishments). Know what to take into prison before they’re in the van. When they get to reception, they’ll thank you.

How the Property System Differs by Prison Category

I’ve served in Cat B, Cat C, and Cat D prisons. The property system is theoretically the same, but the reality changes based on the security level of the establishment.

Category A Dispersals (HMP Pentonville, HMP Belmarsh, etc.): These are the most secure. What to take into prison in a Cat A is extremely restricted. You get minimal belongings on the wing. Almost everything else goes straight into storage. Clothing is checked for concealment opportunities. Shoe soles are inspected. I’ve never been in a Cat A as a regular prisoner, only during transfers, but the reputation is accurate—they’re thorough to the point of paranoia.

Category B (HMP Brixton, HMP Leeds, etc.): Medium security. What to take into prison is fairly standard. You can keep reasonable amounts of personal items on your wing. One watch is fine. Toiletries are fine. Clothing is checked but not obsessively. Property storage is available but not mandatory for all items. I’ve been in three Cat Bs, and the biggest difference between them is the staff’s interpretation of rules, not the rules themselves. HMP Brixton is stricter than HMP Leeds, for example.

Category C (HMP Downview, HMP Standford Hill, etc.): Lower security, long-term. What to take into prison can be more relaxed because there’s less immediate danger. You can keep more on your wing. You have more access to property if it’s stored. Visits are longer, so bringing items for visits is easier. The system works more smoothly because there’s less gang activity and less violence.

Category D Open Prisons (HMP Askham Grange, HMP The Verne, etc.): What to take into prison is almost normal. You keep most belongings with you. You can have a small TV if you bring one (though it needs to be checked). You have more freedom to arrange your space. However, security is still applied—phones are still banned, contraband is still checked—but the atmosphere is less restrictive.

These differences matter when you’re planning what to take into prison. If you know you’re going to a Cat C or Cat D, you can pack slightly differently than if you’re going to a Cat B. It’s not dramatic, but it helps.

One more thing: the prison you first arrive at might not be your final destination. Especially for Cat B prisoners, you might be moved after allocation. What to take into prison should be flexible enough to work across different establishments. Generic neutral clothing works everywhere. Specific branded items cause problems everywhere.

Frequently Asked Questions About What to Take Into Prison

Final Thoughts: You’re More Prepared Now Than You Were

When I walked into HMP Pentonville reception, nobody had explained any of this to me. I made mistakes—expensive, emotionally costly mistakes. I brought the wrong things. I didn’t bring the right documents. I lost items because I didn’t understand the property system. And it all made my first week so much harder than it needed to be.

If you’re reading this because you’re going to prison, or someone you care about is, you’re already ahead of where I was. You know what to take into prison. You understand why certain items matter and why others will cause problems. You know how the property system works. You know what’s banned and why. You’ve got this.

One last thing: be kind to the reception officers. They process hundreds of people. They’re not trying to ruin your day. They’re doing a job. If you arrive unprepared, they’ll spend longer processing you and that’s frustrating for them. If you arrive organised, with documents ready, with a clear understanding of what to take into prison, the process is smoother for everyone. It’s one small thing you can control on what will be a chaotic day.

You’re going to do okay. You’ve already got the information. Now just execute it.

Need more information about starting your sentence? Check out our guides on how to email a prisoner, prison visits explained, and what you can send to prisoners. If you’re entering a specific prison category, our guides on Category B prisons and Category C prisons will give you more context.

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