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Double Bass Roller breaking strings?

I've played guitar for over 40 years, electric bass for 30, and I recently rented an upright bass for a few months to learn to play. It's a cheap rental, so I don't want to sink a lot of money into it. I bought an inexpensive suction-cup transducer mic for it. The strings are of indeterminate age and look like they came from different sets, so I decided to buy a cheap set of strings from ebay after reading someone here at TB saying they were ok.

I installed the new strings, but the D string broke when I brought it up to tune. I got another D string and that also broke bringing it up to tune (although I let it sit and stretch a while before bringing it up all the way). I threw the original D back on and THAT broke as well.

Every time the string broke it broke at the machine roller, so I examined the roller. I noticed that the roller, rather than being totally round, is flattened on the sides where the hole enters and exits (exaggerated in the attached drawing. I'm wondering if this is creating a "corner" on which the strings are breaking. Is this kind of roller normal on uprights? Might it help if I wrap some kind of thin rubber around the roller to soften that edge? Any input is appreciated.
 

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I would suggest checking the nut. It seems likely that the string is binding and causing excessive tension at that sharp bend. Make sure that the nut slot is properly sized for the string and that you line the strings up to run straight out of the nut to the post. Also lubricate the nut and bridge slots with a pencil lead.
 
Yes, I'm putting the string through the barrel and letting it stick out about 3/4" and making the turns. Having never changed strings on an upright before, I read several online guides before I got started.

I'm thinking of getting a piece of tire inner tube to wrap over the barrel.
 
I would suggest checking the nut. It seems likely that the string is binding and causing excessive tension at that sharp bend. Make sure that the nut slot is properly sized for the string and that you line the strings up to run straight out of the nut to the post. Also lubricate the nut and bridge slots with a pencil lead.

I've been using a product called Big Bend's Nut Sauce to coat the notches in the nuts of guitars and electric basses for years; it's a great graphite-based lubricant. I used it on the upright as well; the slots look like the right size except for the E which looks a little wide. But it doesn't appear to be breaking at the nut; it looks like it's breaking up at the barrel (roller) - the core snaps and the winding unravels starting from the barrel.
 
I still wouldn't discount the nut slots. Even if they are well lubed they might still pinch if not shaped properly. Also, you might remove the tuners from the bass and soften any sharp edges on the pegs with a dremel. Does the string touch the G peg or the pegbox? This is somewhere to look for friction.

Last note: Steel upright strings almost never break. I've never had it happen in 20+ years, nor have any friends ever mentioned it. What strings were they? There's mos def something very wrong.
 
They were a set of cheap strings (Patrick brand) I found on ebay. I found a thread here where someone said they were decent. As I said in my original post, the bass is a rental with strings of evidently different brand and age, and I wasn't going to spend a lot of money on strings for a rented bass. The strings it came with sounded like crap, and I just wanted to see what a set of similar strings would sound and feel like. I researched and read about 10 different articles and toughness videos on restringing before I got started in order to beware of the pitfalls.

The core of the string was breaking at tbe barrel and the winding unravelling from there. As it turned out, after writing to him, the ebay seller sent me two D strings to replace those that broke. I wrapped a layer of tire inner tube around the barrel as I wound the string, and that did the trick - I tuned it up to D.
 
I'll give a second for used strings. When I first got a db I tried some eBay cheapies. They were a vast improvement over what came originally on the bass but Helicore pizz proved to be infinitely better in tone and playability. I would try getting a used set, play them until you return the bass, and send it back with the eBay specials installed.