In order to compare the Height/Width properties of the PictureBox and the Picture, you need to ensure they are using the same unit of measurement.

The values of the PictureBox.Picture.Height/Width properties are in HiMetric units.

For comparison, use the values of the PictureBox.ScaleHeight/ScaleWidth properties which are in the ScaleMode of the PictureBox.

Code:
    Dim lngHeight As Long
    Dim lngWidth As Long
    
    lngHeight = Picture1.ScaleY(Picture1.Picture.Height, vbHimetric, Picture1.ScaleMode)
    lngWidth = Picture1.ScaleX(Picture1.Picture.Height, vbHimetric, Picture1.ScaleMode)
    
    If lngHeight > Picture1.ScaleHeight Or lngWidth > Picture1.ScaleWidth Then