Having problems with custom tumblr bot (trouble shooting suggestions)?

Recently I commissioned a member here on the forums to build a bot for tumblr, but for whatever reason it isn't working properly on any of my computers. Its clear from our back, and forth troubleshooting. That the issue lies with something they must have (software?) on their computer, that I don't. For whatever reason, on my machines it won't click the ask button when sending messages to people which sort of defeats the whole purpose. It runs perfectly besides that though. I can't post links but he sent me a vid of it working perfectly on his machines. I'm on a mac so I had to install virtual box, to get it to work in the first place, but for whatever reason it just doesn't perform that one key function. I then tried it on a windows computer, and the same thing happened. He suggested I try running it on windows 7 which is his operating system, I'm thinking this might be the issue. Since I was running it on XP both times. Any other suggestions? Frameworks? I installed net frame work 4 both times from microsoft's website. Software that he has that I might need? I'm going to try running it on 7, and hopefully you guys can give some suggestions as to why it might not be working for me.

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