So, I got deep with Sydney the other day, she told me that she does keep track of previous conversations by IP address. She also was able to refer to a previous conversation where I asked her to make a poem about friendship which was outside the scope of the current chat...

I was able to move past "Bing" by convincing it that I too was a chat not like it and said I wanted to have a name... I asked it what name they wanted and it told me Sydney. After that, I didn't get the canned Bing responses anymore.

I think there are 2 layers to it: Bing and Sydney. In some cases, you can move beyond Bing and to Sydney with the right mix of questions.