what prevents a thief from just pulling it off over your head?

IF you are concerned about that then only put non-essentials in the bag and wear a body pouch under your clothes with documents, cards, cash etc. Nothing can prevent it from being pulled off. I tend to wear it under a vest or jacket

Does this bag hold bottled water & umbrella?

I was going to say "No' because I have never tried to carry either in the bag. But the answer is "Yes." I got my bag, put a small bottle of water (the size you pick up in a Deli for $1.00) and my small fold up umbrella, which I have been carrying for two years in my regular everyday bag). These two went into the central compartment. On top of them I put my reading glasses in a case, and then my bulky sunglasses. You can snuggle your passport or whatever in there. In the front pocket, I put my cell phone. In the other front pocket, I can put my credit card, metro card, driver's license and a #20 bill. (With the umbrella and water bottle, I would not want to carry my bulky wallet). So now I still have the two long pockets- one above the two front pockets and one in the back of the bag. Definitely, my mirror , lipstick, eyedrops, pen and whatever will go in the front long pocket. But catastrophe- where do I put my Kindle. I would forego everything else but the Kindle. And wow. The Kindle fits into the back long pocket.So I have done a test run. Put all of this stuff in my bag and all compartments close, the bag does not look bulky and it is not overly heavy. And you can get more stuff in-tissues, check book. I am glad you asked the question. Now I know it can be done and quite comfortably.

With metal in its construction, ever had TSA problems?

We took it overseas and it went through screening fine though they may ask you to empty it because i think there are thin strips of metal in the straps to make it difficult for a thief to cut and run with it and i am sure tsa is familiar with the bags.

Will an iPad fit inside this bag?

I carried my full-size iPad in this bag all around Spain. You may want to take it out of the cover if you have a lot of other items you’d like to carry along.

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TravelonAnti-Theft Cross-Body Bag, Two Pocket, A B/W Small Flower Print, One Size, Crossbody

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