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So I want to design a button that when pushed would bring up a small pop up window that would ask for input from the user. I would prefer to make this input a selection from a drop down menu.

Then I want to take that information and send it to another visualforce and populate certain fields with it. Should I use the custom button from the Salesforce developer site? If so how do I make it bring up a prompt window?

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Unfortunately, using a standard custom button, this isn't possible. You may be able to do some tricks by creating a button with Content Source set to Visualforce and then executing some Javascript as soon as the page begins to load, but they would have to be directed to that page first.

Now, if you didn't need to use the drop down, this may not be as big of an issue. You may be able to do something using Javascript's prompt() method, but that uses a input box.

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