This behavior was discovered and briefly discussed during the previous dev meeting. The actual warning is
test.rb:4: warning: duplicated 'when' clause with line 2 is ignored
According to @nobu (Nobuyoshi Nakada), this reads "The 'when' clause at line 4 duplicates (conflicts) with (a 'when' clause at) line 2. This is ignored."
Anyway I agree that it is too confusing. I think it would be good if they could improve the English.