Hi, the system will create a TR based on your material document (goods receipt for PO).
It will create one TR for your material document, with more than one item.
When the system creates the TR, you can "convert" it to TO, and your TO should have more than 1 item, so it will be 1 TO by default, but for more than one item.
So your last picture would be OK if you only corrected that 3 green TO labels would say:
TO #1 item #1
TO #1 item #2
TO #1 item #3
Regards,
Mihailo