diff --git a/builder/vsphere/common/step_add_cdrom.go b/builder/vsphere/common/step_add_cdrom.go
index 749efce5..d7654b1d 100644
--- a/builder/vsphere/common/step_add_cdrom.go
+++ b/builder/vsphere/common/step_add_cdrom.go
@@ -74,7 +74,9 @@ func (s *StepAddCDRom) Run(_ context.Context, state multistep.StateBag) multiste
 	}
 
 	if path, ok := state.GetOk("iso_remote_path"); ok {
-		s.Config.ISOPaths = append(s.Config.ISOPaths, path.(string))
+		// The order matters: docs say "iso_url" should go first, so make sure to
+		// prepend it.
+		s.Config.ISOPaths = append([]string{path.(string)}, s.Config.ISOPaths...)
 	}
 
 	// Add our custom CD, if it exists
diff --git a/builder/vsphere/common/step_add_cdrom_test.go b/builder/vsphere/common/step_add_cdrom_test.go
index 1fc808dd..18018cfd 100644
--- a/builder/vsphere/common/step_add_cdrom_test.go
+++ b/builder/vsphere/common/step_add_cdrom_test.go
@@ -96,7 +96,7 @@ func TestStepAddCDRom_Run(t *testing.T) {
 				FindSATAControllerCalled: true,
 				AddCdromCalledTimes:      3,
 				AddCdromTypes:            []string{"sata", "sata", "sata"},
-				AddCdromPaths:            []string{"iso/path", "remote/path", "cd/path"},
+				AddCdromPaths:            []string{"remote/path", "iso/path", "cd/path"},
 			},
 			fail:       false,
 			errMessage: "",