1.  Clipart as originally inserted can’t be rotated. On the Drawing toolbar when you click Draw and then click  on Rotate or Flip, the choices are dimmed (unavailable).

2.  Click on the clipart so it has “handles”, then click on Draw, then click Ungroup.  You may be asked if you want to convert the clipart to a Microsoft Drawing Object.  Click Yes.

The clipart will then have many “handles”.  Each “piece” of the artwork is selected.

3.  Click on Draw in the Drawing toolbar, click Group.

4.  Click on Draw in the Drawing toolbar, click Rotate or Flip.  You should now be able to click your choice.

NOTE:  Unfortunately, this doesn’t always work.  You may have to start the Paint program.  Paste the clipart into Paint, rotate the image, copy it, then go back to your Office document and paste in the rotated clipart.