Pipers,
I agree with Pop, the main lift cables are (and should be) under tension whenever the top is raised.
Frankly, your question is a bit confusing. After raising the top, and deploying the tip-out, are you saying that you then lower the top to rest on the tip-out? And/or, are you saying that the piece of wood, mounted at the top of your tip-out, where the winch cable is attached, is coming loose? And/or, is the entire cabinet, that houses the winch, coming loose at the corners?
The correct operating procedure is to raise the top, all the way, until the ram locking bar engages (typically with a faint "clunk"). Then deploy the tip out all the way until you can engage the manual locking pin (up on the side of the tip-out). If you are deploying the tip-out until the wood side trim rest against the upper half side wall, then you've done it correctly. The locking pin should not be able to engage until the tip out is ALL the way tipped out.
Over time, due to minor hydraulic seepage past the ram, the top of your Hi-Lo will probably drift down until the ram lock is holding it up. This is okay, and safe, but could cause the tip-out to hang-up (including jamming the locking pin). All you need to do if this happens, is raise the top back up... which is normal anyway to release the ram locking bar (by pulling on that little cable by the switch), and then unlocking and retracting the tip out. The tip out should come all the way in until it rests on the floor without tension on winch cable.
Hope this helps. If I've completely missed the problem you're having, give us some photos to look at.
Jim