diff --git a/simplify.c b/simplify.c
index 2f6f41c249dc..9a24058f6e55 100644
--- a/simplify.c
+++ b/simplify.c
@@ -1239,13 +1239,13 @@ static int simplify_compare_constant(struct instruction *insn, long long value)
 			}
 			break;
 		case OP_SET_LT: case OP_SET_LE:
-			if (value >= sign_bit(osize))
+			if (value < sign_bit(size))
 				return replace_with_value(insn, 1);
 			else
 				return replace_with_value(insn, 0);
 			break;
 		case OP_SET_GE: case OP_SET_GT:
-			if (value >= sign_bit(osize))
+			if (value < sign_bit(size))
 				return replace_with_value(insn, 0);
 			else
 				return replace_with_value(insn, 1);
diff --git a/validation/optim/cmp-sext-simm.c b/validation/optim/cmp-sext-simm.c
index a8b2a8f9feff..57a4df1d57b1 100644
--- a/validation/optim/cmp-sext-simm.c
+++ b/validation/optim/cmp-sext-simm.c
@@ -4,21 +4,45 @@
 
 static int lt_ge0(int x) { return (sext(x) <  (POS + 0)) == 1; }
 static int lt_ge1(int x) { return (sext(x) <  (POS + 1)) == 1; }
+static int lt_ge2(int x) { return (sext(x) <  (POS + 2)) == 1; }
+static int lt_gex(int x) { return (sext(x) <  (POS<< 1)) == 1; }
+static int lt_gey(int x) { return (sext(x) <  (POS<< 3)) == 1; }
 static int le_ge0(int x) { return (sext(x) <= (POS + 0)) == 1; }
 static int le_ge1(int x) { return (sext(x) <= (POS + 1)) == 1; }
-static int lt_lt0(int x) { return (sext(x) <  (NEG - 0)) == 1; }
-static int lt_lt1(int x) { return (sext(x) <  (NEG - 1)) == 1; }
-static int le_lt0(int x) { return (sext(x) <= (NEG - 0)) == 1; }
-static int le_lt1(int x) { return (sext(x) <= (NEG - 1)) == 1; }
-
-static int gt_ge0(int x) { return (sext(x) >  (POS + 0)) == 0; }
-static int gt_ge1(int x) { return (sext(x) >  (POS + 1)) == 0; }
+static int le_ge2(int x) { return (sext(x) <= (POS + 2)) == 1; }
+static int le_gex(int x) { return (sext(x) <= (POS<< 1)) == 1; }
+static int le_gey(int x) { return (sext(x) <= (POS<< 3)) == 1; }
 static int ge_ge0(int x) { return (sext(x) >= (POS + 0)) == 0; }
 static int ge_ge1(int x) { return (sext(x) >= (POS + 1)) == 0; }
-static int gt_lt0(int x) { return (sext(x) >  (NEG - 0)) == 0; }
-static int gt_lt1(int x) { return (sext(x) >  (NEG - 1)) == 0; }
-static int ge_lt0(int x) { return (sext(x) >= (NEG - 0)) == 0; }
-static int ge_lt1(int x) { return (sext(x) >= (NEG - 1)) == 0; }
+static int ge_ge2(int x) { return (sext(x) >= (POS + 2)) == 0; }
+static int ge_gex(int x) { return (sext(x) >= (POS<< 1)) == 0; }
+static int ge_gey(int x) { return (sext(x) >= (POS<< 3)) == 0; }
+static int gt_ge0(int x) { return (sext(x) >  (POS + 0)) == 0; }
+static int gt_ge1(int x) { return (sext(x) >  (POS + 1)) == 0; }
+static int gt_ge2(int x) { return (sext(x) >  (POS + 2)) == 0; }
+static int gt_gex(int x) { return (sext(x) >  (POS<< 1)) == 0; }
+static int gt_gey(int x) { return (sext(x) >  (POS<< 3)) == 0; }
+
+static int lt_lt0(int x) { return (sext(x) <  (NEG - 0)) == 0; }
+static int lt_lt1(int x) { return (sext(x) <  (NEG - 1)) == 0; }
+static int lt_lt2(int x) { return (sext(x) <  (NEG - 2)) == 0; }
+static int lt_ltx(int x) { return (sext(x) <  (NEG<< 1)) == 0; }
+static int lt_lty(int x) { return (sext(x) <  (NEG<< 3)) == 0; }
+static int le_lt0(int x) { return (sext(x) <= (NEG - 0)) == 0; }
+static int le_lt1(int x) { return (sext(x) <= (NEG - 1)) == 0; }
+static int le_lt2(int x) { return (sext(x) <= (NEG - 2)) == 0; }
+static int le_ltx(int x) { return (sext(x) <= (NEG<< 1)) == 0; }
+static int le_lty(int x) { return (sext(x) <= (NEG<< 3)) == 0; }
+static int ge_lt0(int x) { return (sext(x) >= (NEG - 0)) == 1; }
+static int ge_lt1(int x) { return (sext(x) >= (NEG - 1)) == 1; }
+static int ge_lt2(int x) { return (sext(x) >= (NEG - 2)) == 1; }
+static int ge_ltx(int x) { return (sext(x) >= (NEG<< 1)) == 1; }
+static int ge_lty(int x) { return (sext(x) >= (NEG<< 3)) == 1; }
+static int gt_lt0(int x) { return (sext(x) >  (NEG - 0)) == 1; }
+static int gt_lt1(int x) { return (sext(x) >  (NEG - 1)) == 1; }
+static int gt_lt2(int x) { return (sext(x) >  (NEG - 2)) == 1; }
+static int gt_ltx(int x) { return (sext(x) >  (NEG<< 1)) == 1; }
+static int gt_lty(int x) { return (sext(x) >  (NEG<< 3)) == 1; }
 
 /*
  * check-name: cmp-sext-simm
