In the Administer | Tablespaces, one selects the Files tab and clicks the Calculate icon to calculate reclaimable space.
One selects more than one tablespace file and clicks the ‘Shrink to Minimum’ icon.
In version 12.5.x, nothing happens.
This worked properly in version 12.1.
WORKAROUND:
Revert back to Toad for Oracle version 12.1
As another possible workaround is that a single tablespace may be shrunk at a time and the process is repeated.
STATUS:
Waiting for fix in a future version of Toad for Oracle.