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Do you mean an image map (an image with some hotspots on it that link to other topics)? If so, insert the image. Then right click on it and select Insert Image Map.
When you see a message asking if you would like to overwrite, RoboHelp is generally advising that you are bringing another copy of the image that has the same file name. If it's the same image, no harm done. Allow it to proceed. But if the image is different, you may wish to give it a second look.
What I actually envisioned was the user mousing over the word Wizard icon and getting a view of the icon as well as a brief description. In a perfect world I guess. But the main question I have is why do I get this overwrite message and what happens if I click yes to overwrite? What am I overwriting exactly and why am I being asked if I want to overwrite anything. I just want to insert an image. I guess I'm confused by this functionality.
Perhaps it will help to remove RoboHelp form the picture and think purely in terms of Windows Explorer and files. Let's say you have a folder named C:\Images.
You have another folder named C:\Projects.
You copy an image named MyImage.gif from C:\Images to C:\Projects. The first time you do this, the image doesn't exist in C:\Projects so it is simply copied.
Perhaps you try to copy the image again. This time you should see a message that is basically saying Stop and pay attention! You already have an image in this location that is using the same file name as what you are about to copy. Are you certain?
RoboHelp is basically doing the same thing. It knows you already have an image in the project that is using that name. So it is having you decide upon how it should behave.
Unfortunately we can't tell you which action is appropriate. Only you will know that for certain and here's why. Assuming you have already used this image and you didn't change the image, you are probably safe in allowing RoboHelp to copy the new image and overwrite the old one. As I said earlier, as long as it's the same image no harm will be done. But if perhaps you are using images from multiple locations, maybe you found one on the web you are wanting to use and it's named identically to another image you already are using in the project, you would want to think twice about proceeding. Because if you do, you will replace the first image with the second and that can have some serious consequences.
Sorry, but without watching what you are doing first hand it's a bit difficult to know how to advise. All we can do is to provide generalities.