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1. What is the difference between keeping resample on and keeping it off?
I want to enlarge a picture and make it 300 ppi.
2. When do i need to keep the resample checked or unchecked?
Entirely depends on what kind of effect you want. Resizing images without resampling will simply duplicate pixels (upsizing) or eliminate every n-th one (downsizing) and give that pixely GIF look. Using no resampling sometimes can be useful for graphical elements with large uniformely colored areas, since it keeps edges sharp while resampling is uesed pretty much for everything else. There's no general recipe what's right and what's wrong and you ahven't provided enough info, anyway.
Mylenium
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Entirely depends on what kind of effect you want. Resizing images without resampling will simply duplicate pixels (upsizing) or eliminate every n-th one (downsizing) and give that pixely GIF look. Using no resampling sometimes can be useful for graphical elements with large uniformely colored areas, since it keeps edges sharp while resampling is uesed pretty much for everything else. There's no general recipe what's right and what's wrong and you ahven't provided enough info, anyway.
Mylenium
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A file is just pixels. Pixels have no size - you assign a print size by setting a ppi (pixels per inch) value. Pixels per inch - do the math.
This becomes much easier to grasp if you sit down and consider what pixels per inch really means. When you understand this, the rest becomes self-explaining.
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By the way, you can't make a small picture good by enlarging it. Generally pointless. Get a bigger starting point.