Whenever I try to create my own user icon in Microsoft Paint, When I upload it for it to be my icon, it always says File is to large to upload. How do I shrink the file size?
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Try resaving the icon as GIF. It could reduce the size a bit. What format did you save as?

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Paint saves files as .bmp (I think, I don't use Windows very much), which usually are big. What FlyingHatTrick said is right, convert to a .gif. That will work much better.
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