diff --git a/prow/cmd/checkconfig/main.go b/prow/cmd/checkconfig/main.go
index 1ce479dc5277..97283b1b7665 100644
--- a/prow/cmd/checkconfig/main.go
+++ b/prow/cmd/checkconfig/main.go
@@ -1053,22 +1053,33 @@ func verifyOwnersPlugin(cfg *plugins.Configuration) error {
 }
 
 func verifyLabelPlugin(label plugins.Label) error {
-	var orgRepos []string
+	var orgReposWithEmptyLabelConfig []string
+	var errs []error
+	restrictedAndAdditionalLabels := make(map[string][]string)
 	for orgRepo, restrictedLabels := range label.RestrictedLabels {
 		for _, restrictedLabel := range restrictedLabels {
+			if label.IsRestrictedLabelInAdditionalLables(restrictedLabel.Label) {
+				restrictedAndAdditionalLabels[restrictedLabel.Label] = append(restrictedAndAdditionalLabels[restrictedLabel.Label], orgRepo)
+			}
 			if restrictedLabel.Label == "" {
-				orgRepos = append(orgRepos, orgRepo)
+				orgReposWithEmptyLabelConfig = append(orgReposWithEmptyLabelConfig, orgRepo)
 			}
 		}
 	}
 
-	if len(orgRepos) > 0 {
-		sort.Strings(orgRepos)
-		return fmt.Errorf("the following orgs or repos have configuration of %s plugin using the empty string as label name in restricted labels: %s",
-			labelplugin.PluginName, strings.Join(orgRepos, ", "),
-		)
+	for label, repos := range restrictedAndAdditionalLabels {
+		sort.Strings(repos)
+		errs = append(errs,
+			fmt.Errorf("the following orgs or repos have configuration of label plugin using the restricted label %s which is also configured as an additional label: %s", label, strings.Join(repos, ", ")))
 	}
-	return nil
+
+	if len(orgReposWithEmptyLabelConfig) > 0 {
+		sort.Strings(orgReposWithEmptyLabelConfig)
+		errs = append(errs, fmt.Errorf("the following orgs or repos have configuration of %s plugin using the empty string as label name in restricted labels: %s",
+			labelplugin.PluginName, strings.Join(orgReposWithEmptyLabelConfig, ", "),
+		))
+	}
+	return utilerrors.NewAggregate(errs)
 }
 
 func validateTriggers(cfg *config.Config, pcfg *plugins.Configuration) error {
diff --git a/prow/cmd/checkconfig/main_test.go b/prow/cmd/checkconfig/main_test.go
index 4fd9f4d5e110..43d2b76617f8 100644
--- a/prow/cmd/checkconfig/main_test.go
+++ b/prow/cmd/checkconfig/main_test.go
@@ -2281,6 +2281,45 @@ func TestVerifyLabelPlugin(t *testing.T) {
 			},
 			expectedErrorMsg: "the following orgs or repos have configuration of label plugin using the empty string as label name in restricted labels: orgRepo1, orgRepo2",
 		},
+		{
+			name: "invalid when additional and restricted labels are the same",
+			label: plugins.Label{
+				AdditionalLabels: []string{"cherry-pick-approved"},
+				RestrictedLabels: map[string][]plugins.RestrictedLabel{
+					"orgRepo1": {
+						{
+							Label: "cherry-pick-approved",
+						},
+					},
+				},
+			},
+			expectedErrorMsg: "the following orgs or repos have configuration of label plugin using the restricted label cherry-pick-approved which is also configured as an additional label: orgRepo1",
+		},
+		{
+			name: "invalid when additional and restricted labels are the same in multiple orgRepos and empty string",
+			label: plugins.Label{
+				AdditionalLabels: []string{"cherry-pick-approved"},
+				RestrictedLabels: map[string][]plugins.RestrictedLabel{
+					"orgRepo1": {
+						{
+							Label: "cherry-pick-approved",
+						},
+					},
+					"orgRepo2": {
+						{
+							Label: "",
+						},
+					},
+					"orgRepo3": {
+						{
+							Label: "cherry-pick-approved",
+						},
+					},
+				},
+			},
+			expectedErrorMsg: "[the following orgs or repos have configuration of label plugin using the restricted label cherry-pick-approved which is also configured as an additional label: orgRepo1, orgRepo3, " +
+				"the following orgs or repos have configuration of label plugin using the empty string as label name in restricted labels: orgRepo2]",
+		},
 	}
 
 	for _, tc := range testCases {
diff --git a/prow/plugins/config.go b/prow/plugins/config.go
index 6620d4ec0b69..7c38a8166da5 100644
--- a/prow/plugins/config.go
+++ b/prow/plugins/config.go
@@ -401,6 +401,15 @@ func (l Label) RestrictedLabelsFor(org, repo string) map[string]RestrictedLabel
 	return result
 }
 
+func (l Label) IsRestrictedLabelInAdditionalLables(restricted string) bool {
+	for _, additional := range l.AdditionalLabels {
+		if restricted == additional {
+			return true
+		}
+	}
+	return false
+}
+
 type RestrictedLabel struct {
 	Label        string   `json:"label"`
 	AllowedTeams []string `json:"allowed_teams,omitempty"`