I am facing my 2nd surgery for uterine/bladder prolapse. is there a greater risk for incontinence this time? and can this happen over and over?

Depends: Surgical skill is important, but your underlining condition is a problem. Did you go for 2 nd opinion. What is the success rate of this surgeon with other patients?

Not greater risk: This time in particular, but there is always a risk of new and persistent bladder problems - including incontinence - with any prolapse surgery. Recent studies suggest that in some cases, even if you don't have incontinence it might make sense to include a urethral sling as part of your surgery to prevent it. You should discuss this with your surgeon. And yes, unfortunately, prolapse can recur.