Chance are that you have two instances of the JLabel. One is a class variable and one is an instance variable which has been added to the GUI. The problem is your code is updating the class variable.
Or, maybe if you don't update the icon on the EDT you might have problems.
Edit: Just reread the question. If you are talking about a "generated image" that needs to be reloaded from a file, then you need to get rid of the cached image. Two ways to do this:
// Using ImageIO
String imageName = "timeLabel.jpg";
imageLabel.setIcon( new ImageIcon(ImageIO.read( new File(imageName) ) ) );
// Or you can flush the image
String imageName = "timeLabel.jpg";
ImageIcon icon = new ImageIcon(imageName);
icon.getImage().flush();
imageLabel.setIcon( icon );
If you need more help post your SSCCE.
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