I work for a large company that is set back from the street and has some bike racks that are within courtyards and not visible from the street so only employees see the rack when walking outside the building. I rode my bike to work for the first time and still did not feel comfortable leaving it outside. I only have one bike and to the untrained observer it looks nice since it's a road bike and not a beater mountain bike. Today I asked the security guys if I could leave it inside and I put it in a storage closet but it seems like it's a one time deal and they prefer if I just leave it outside. Am I being overly hesitant and would you lock it up outside if you were in my position? i only have a cable lock, not a U lock or anything.

No mechanical lock is impenetrable with today's battery powered tools and an abrasive blade. But if the rack is in a private area, near the entrance or with windows overlooking it, and not full of bikes, and in Hoboken, not Jersey City, you probably have a chance. Do you leave the Trek 1.2 unattended elsewhere in HB?

The cable lock should be at least as thick as your index finger.

Ask your HR Department if your bike is covered under their insurance... Sometimes they react in your favor of bringing it inside.

HR would probably respond "Insured? For what, and why should it? But if it will make you happy we will remove the bike rack."

My bike never comes inside. When I drive I leave my car parked outside too.

It would suck if either of them got stolen or vandalized. However, life goes on and if you're taking reasonable precautions against theft then beyond that you just have to accept the fact that you can't control every single circumstance.

In my 40 years of riding I've had three bikes stolen. Two were taken out of my garage and one was stolen outside of an arcade (I was a kid.) Never had one messed with when locked up outside my workplace.

I would invest in a U lock. The Kryponite mini costs $40, but buys a lot of peace of mind.

What's the most (reasonably) secure way to lock a bike to a bike rack?

I have an older version of an 8mm cable lock. Wow, didn't realize how inexpensive one of these are these days, like 12 bucks. Any advice on which lock to get? There are like 10 kinds of Kryptonite ones - maybe I should get the Mini, or something in the $35 range? I don't know if the $100 lock is any better of a deterrent than the $35 one.

My company will not be held responsible for anything left outside, even cars we park in the lot. They said they have never heard of an attempted bike theft but there is only one or two people that ride to work and my building has a thousand people in it. That's why I wanted to bring it inside, even if they thought I was crazy.

I don't work in those cities, I work off of the Palisades in North Jersey. I never lock up my bike outside - when I have run errands before I just bring my bike into the store for a few minutes and leave it against a wall.

I have sometimes been able to bring a bike inside, in which case it is nice to use a road bike for a faster commute. My road bikes are too nice to leave locked up anywhere for long periods.

Outside of that, I'd suggest getting a less attractive bike on Craigslist and put your mind at ease. I have Velo Orange bolt-on skewers on my MTB commuter (they require a special 5mm hex key), and use 2 Kryptonite U-locks for extended lock-ups. One is standard, locking the front wheel to the frame and the other is a giant New York lock that weighs about 5lbs.

Sheldon's take on bike locking strategy.

Every time I see Sheldon Brown quoted, my mind first pictures Sheldon from The Big Bang Theory.

Is it possible to leave a sturdy U-lock at work? That doesn't guarantee that your bike won't be stolen, but it probably means that someone else's bike is an easier target, especially if you use the U-lock and your cable lock.

Get two u-locks, leave them on the rack. If you look around, you can find u-locks for as little as $10. How is the seatpost secured?

Seatpost is secured by an allen key, it's not quick release. But I'm not concerned about anyone taking my seat.

Where can I find a U-lock for 10 bucks?

It depends on the neighborhood. How far off the road is the office park? What kinds of people work there? I worked at various AT&T locations in NJ suburbs. They were in fancy neighborhoods, far from the road. People locked their bikes to the bike racks, but that seemed redundant. No one ever messed around there.

I'm pretty lucky. I'm in an office park but much smaller. Only 20 employees and I'm the only cyclist.

I lock my bike to a tree that is about 20 feet from a window shared by me and a few others. Anyone trying to tamper would be noticed pretty easily. I even just leave my helmet on the handlebars, unlocked.

I do leave the cable lock here, around the tree. It's too bulky to carry every day and at home the bike is in the garage.

I lock my road bike up daily at the office park and don't think twice about it. Sometimes I don't even lock it. But like noglider said it depends on the office, the area and security.

In your shoes I'd probably find a solid u-lock, maybe a heavy chain, and leave it at the rack permanently.

Both the times I found u-locks for 10 bucks, was while ordering bike parts online and going through what was on sale in addition to what I was there to order. IIRC, one time it was from Mission Bikes (they have a good u-lock holster I was buying), but I'm not seeing them there now. I got the very last one from wherever I scored my last 10 dollar one, because I remembered wanting to order two and them only having one left. Another close-out of cheap u-locks. One of the benefits of always seeming to be ordering parts because I'm building up and maintaining a fleet of six bikes (city bike/tourer/MTB x two people), is that I'm getting some of my parts and accessories on sale because I'm getting e-mails from all these places I've ordered from in the past, or I'm on a site ordering anyway and see what else I should buy as long as I'm there paying for their shipping anyway.

A quick google search did turn up this:
18cm Width Blue Metal Bike Motorcycle Security U Lock w 2 Keys

Sunlite also makes a u-lock for about 10 bucks, I guess the trick is to be already ordering some parts from somewhere online, as otherwise it looks like the shipping for the lock doubles it's price, although if you split that over two locks, they get close to about 15 bucks a piece. There's at least a half dozen places google lists selling those, including Niagara Cycle Works and Bike Wagon.

For wearing on me or going around town I prefer to carry a nicer lock, but for the rack at work, I have one of my crappiest u-locks. Work is pretty safe, and I've got a couple of those Sunlites and they're a little awkward to portage due to their shape. Staying on the rack at work they're fine though. They're not nice locks, the mechanism is just a little fiddly, but like I said, works fine for a lock left on a rack at work. Two of them should be enough deterrent for your situation.

The chain is a good recommendation IMO. I've done that a couple of times, gone to the hardware store and bought as much chain as I'd need to run through the wheels, frame and rack, and bought a good padlock to go with it. Such a chain should be sufficient for this kind of location, and a LOT less expensive than the bike specific ones. You can wrap the chain in an old inner tube (it'll slide right into a big mountain tube) if you're worried about your bikes finish.

Right now my chains almost always stay at home, but every now and then I'll take one with me depending on where I'm going.

You you are worried, I suggest multiple locks. No one ever had their bike stolen from using too many locks, and since it is just employees and such, you can probably get away with leaving a U-Lock or 2 attached to the bike rack (cause them things are heavy! At least mine is...I use an OnGuard). The only time I have left my bike outside for more than an hour or so was overnight in Savannah locked to the bike rack outside of my hotel. It was fine there. I would have a Ulock attaching the frame to the bike rack, another attaching the front wheel to the frame, and then a cable lock running through your seat and also around the bike rack. Chances are even if you forgo the 2nd Ulock, if you have more than 1 lock on your bike a potential thief will just move onto an easier target. If you do that, make sure you still lock your front wheel to your frame, or get rid of the quick release skewers in favor of a bolt on. I picked up a set for like 10 bucks that requires a special hex key to take the wheel off. Nothing on my commuter is a quick release.

I am fortunate though that I get to bring my bike inside my work.

Two U-locks and a 5/8" cable with a mini U-lock... I leave them all there over night.

Target (and probably others) carries a Masterlock u lock for $15. I used to use one before I upgraded to Kruptonite. Never had a bike stolen, though from the looks of it, no one ever tried.

You can find them for free on cheaply made bike racks all over the place. The tricky part is how to get the key.

Don't get 1 $10 U-Lock. Get a good quality one. I recommend the Kryptonite orange or yellow lines since they lock both legs and a theif would have to cut them twice to steal the bike. I also recommend a cable for the wheels--you can probably use your old cable lock for this. If you don't want to carry the lock around, leave it on the rack and just bring the cable lock with you.

It might be worth it to invest in a beater. I name all my bikes even though they aren't worth much. The thought of them being stolen makes my brain curdle so no I would not leave them locked up outside for a full shift. The longest I ever leave them is for the occasional doctors appointment. If it's an out of the way office lot with average security they may be more likely to be stolen since security probably doesn't give a damn and there aren't that many casual strollers around to see someone with an angle grinder or bolt cutters. They'd probably be too busy elsewhere to notice anything unusual. If they're worthy guards though it should be fine but if they're not I would only lock up a sub 400 dollar bike. You don't really have a way of knowing what kind of guards they are until you have a few casual conversations with them or see them react to something.