diff --git a/llvm/test/Transforms/InstSimplify/and-or-icmp-zero.ll b/llvm/test/Transforms/InstSimplify/and-or-icmp-zero.ll
index eb1d05d1822c..3e50a5968b46 100644
--- a/llvm/test/Transforms/InstSimplify/and-or-icmp-zero.ll
+++ b/llvm/test/Transforms/InstSimplify/and-or-icmp-zero.ll
@@ -262,3 +262,29 @@ define i1 @and_cmps_ptr_eq_zero_with_mask_commute4(ptr %p, i64 %y) {
   ret i1 %r
 }
 
+; tests from PR66606
+define i32 @and_zext_eq_zero(i32 %a) {
+; CHECK-LABEL: @and_zext_eq_zero(
+; CHECK-NEXT:    [[COND:%.*]] = icmp eq i32 [[A:%.*]], 0
+; CHECK-NEXT:    [[NOT:%.*]] = zext i1 [[COND]] to i32
+; CHECK-NEXT:    [[R:%.*]] = and i32 [[A]], [[NOT]]
+; CHECK-NEXT:    ret i32 [[R]]
+;
+  %cond = icmp eq i32 %a, 0
+  %not = zext i1 %cond to i32
+  %r = and i32 %a, %not
+  ret i32 %r
+}
+
+define i32 @and_zext_eq_zero_commuted(i32 %a) {
+; CHECK-LABEL: @and_zext_eq_zero_commuted(
+; CHECK-NEXT:    [[COND:%.*]] = icmp eq i32 [[A:%.*]], 0
+; CHECK-NEXT:    [[NOT:%.*]] = zext i1 [[COND]] to i32
+; CHECK-NEXT:    [[R:%.*]] = and i32 [[NOT]], [[A]]
+; CHECK-NEXT:    ret i32 [[R]]
+;
+  %cond = icmp eq i32 %a, 0
+  %not = zext i1 %cond to i32
+  %r = and i32 %not, %a
+  ret i32 %r
+}