You need to call either Refresh()
or Invalidate()
function on PictureBox
control to Update it after Rotating.
From MSDN:Invalidate
Invalidates the entire surface of the control and causes the control to be redrawn.
Try : using Invalidate()
private void button1_Click(object sender, EventArgs e)
{
pictureBox1.Image.RotateFlip(RotateFlipType.Rotate90FlipNone);
pictureBox1.Invalidate();
Application.DoEvents();
}