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Handling pop-ups and other interactive display changes can be a challenge, regardless of the tool. You might consider a couple of approaches. First, be active in the tool's user group, seeking solutions. There are several groups available on the Internet -- just pick one or two. Be polite: post your question once, rather than blasting across multiple groups. If you post to the Selenium user's group, you will definitely encounter other testers who have faced similar challenges in the past -- they'll probably have tried-and-true solutions for you. If you do ask for help, please follow the suggestions I give in my blog, Thoughts on QA. It'll improve the odds that you'll get a helpful answer!
Secondly, pay close attention to your implementation. If your Web app uses a lot of rich Internet applications (RIAs), your might get away with the use of divs rather than handling each window (in RIA, developers can "pop up" windows which are, in fact, just hidden divs being exposed). Experiment with different programming solutions and see which is more reliable. There is generally more than one way to accomplish what you're trying to do. You're looking for the way which is 1) feasible, 2) most reliable and 3) most performant (in that order).
The third approach may be the most challenging and, in the short term, costly. However, if you're working on an ongoing, long-term project it will have payoff. If the current implementation is not very testable, propose alternative implementations to the development team. For instance, if the current project creates multiple pop-up windows (rather than using Ajax to expose elements), ask that the team take time to change this, implementing a solution which you can test more reliably and in a shorter amount of time. You need to be very, very detailed in your reasoning -- you will need to include schedule and cost savings. Point to gains down the road when your automated regression and functional tests run more reliably. By implementing testability, you will be addressing what Agile teams call "technical debt." You take a short-term hit on schedule, with the outcome being a long-term improvement in effectiveness and efficiency.
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