diff --git a/compiler/optimizer/pruner.go b/compiler/optimizer/pruner.go
index 63bc9352b..96c3ccf92 100644
--- a/compiler/optimizer/pruner.go
+++ b/compiler/optimizer/pruner.go
@@ -138,13 +138,13 @@ func reverseComparator(op string) string {
 	case "==", "!=":
 		return op
 	case "<":
-		return ">="
-	case "<=":
 		return ">"
+	case "<=":
+		return ">="
 	case ">":
-		return "<="
-	case ">=":
 		return "<"
+	case ">=":
+		return "<="
 	}
 	panic("unknown op")
 }
diff --git a/compiler/ztests/pruner.yaml b/compiler/ztests/pruner.yaml
new file mode 100644
index 000000000..fdc9ea5e7
--- /dev/null
+++ b/compiler/ztests/pruner.yaml
@@ -0,0 +1,15 @@
+# Test pruner flips comparator with literal/path
+script: |
+  super -f parquet -o test.parquet -c 'values {v:1}'
+  super compile -O -C -c 'from test.parquet | where 1 <= v and 1 >= v'
+
+outputs:
+  - name: stdout
+    data: |
+      file test.parquet format parquet filter (1<=v and 1>=v)
+         pruner (
+           expr compare(v.max, 1, true)>=0 and compare(v.min, 1, true)<=0
+           fields v.max,v.min
+        )
+      | where 1<=v and 1>=v
+      | output main