Ian Bicking nails it: "Resolving Python's problems with web programming is the most important thing we can do to market Python." Take Ruby. Ruby is getting a lot of attention in the Java community because of Ruby oo Rails, especially because a few high-profile developers think it and ruby in general rocks. If you'd been working with Struts for the last few years, RoR is probably going to be highly appealing certainly compared to the incumbent JSF, or possibly even WebWork+SiteMesh. Ian also said something comments that's worth highlighting: "I personally have resisted the urge to develop a new framework (an urge I've felt many times over the years), and I actually am willing to give up my framework of choice for more conformity. But I can't abandon my framework (and I can't expect anyone else to do so either) -- other people have trusted my opinion and choice over the years, and it would be irresponsible of me to abandon them and those applications I've developed. Which is a bind a lot of us have probably been in." Sounds like an Innovator's Dilemma - customer needs and invested legacy are stifling the ability to innovate. The thing is, what kills you in the end are the low end technologies. Always. What I hadn't realized is that the web frameworks situation in Python is almost as diliuted as Java's. I wonder if this has as much to do with how we think about the web as the programming language we work in....