diff --git a/tools/cli/internal/changelog/outputfilter/squash_test.go b/tools/cli/internal/changelog/outputfilter/squash_test.go
index a530aacb8..147ab6c45 100644
--- a/tools/cli/internal/changelog/outputfilter/squash_test.go
+++ b/tools/cli/internal/changelog/outputfilter/squash_test.go
@@ -139,6 +139,17 @@ func TestExtractExactValuesOrFail(t *testing.T) {
 			want:                   []string{"GROUP_USER_ADMIN", "/items/roles/items/"},
 			wantErr:                require.NoError,
 		},
+		{
+			name:      "Multiple values with empty entries",
+			operation: "test",
+			entry: &OasDiffEntry{
+				ID:          "response-write-only-property-enum-value-added",
+				OperationID: "op1",
+				Text:        "added the new '' enum value to the request property '/items/roles/items/'"},
+			expectedNumberOfValues: 2,
+			want:                   []string{"", "/items/roles/items/"},
+			wantErr:                require.NoError,
+		},
 		{
 			name:                   "Incorrect number of values",
 			operation:              "test",