diff --git a/tests/unit/compiler/venom/test_sccp_algebraic.py b/tests/unit/compiler/venom/test_sccp_algebraic.py
index 1103363314..875dce6b97 100644
--- a/tests/unit/compiler/venom/test_sccp_algebraic.py
+++ b/tests/unit/compiler/venom/test_sccp_algebraic.py
@@ -8,7 +8,6 @@
     RemoveUnusedVariablesPass,
     StoreElimination,
 )
-from vyper.venom.passes.sccp.eval import signed_to_unsigned
 
 """
 Test abstract binop+unop optimizations in sccp and algebraic optimizations pass
@@ -380,7 +379,7 @@ def test_comparison_almost_never():
 
     max_uint256 = 2**256 - 1
     max_int256 = 2**255 - 1
-    min_int256 = 2**255
+    min_int256 = -(2**255)
     pre = f"""
     _global:
         %par = param
@@ -418,7 +417,7 @@ def test_comparison_almost_always():
 
     max_uint256 = 2**256 - 1
     max_int256 = 2**255 - 1
-    min_int256 = 2**255
+    min_int256 = -(2**255)
 
     pre = f"""
     _global:
@@ -466,15 +465,15 @@ def test_comparison_ge_le(val):
     up = val + 1
     down = val - 1
 
-    val = signed_to_unsigned(val, 256)
-    up = signed_to_unsigned(up, 256)
-    down = signed_to_unsigned(down, 256)
+    abs_val = abs(val)
+    abs_up = abs_val + 1
+    abs_down = abs_val - 1
 
     pre = f"""
     _global:
         %par = param
-        %1 = lt %par, {val}
-        %3 = gt %par, {val}
+        %1 = lt %par, {abs_val}
+        %3 = gt %par, {abs_val}
         %4 = iszero %3
         %2 = iszero %1
         %5 = slt %par, {val}
@@ -486,8 +485,8 @@ def test_comparison_ge_le(val):
     post = f"""
     _global:
         %par = param
-        %1 = lt {down}, %par
-        %3 = gt {up}, %par
+        %1 = lt {abs_down}, %par
+        %3 = gt {abs_up}, %par
         %5 = slt {down}, %par
         %7 = sgt {up}, %par
         return %1, %3, %5, %7
diff --git a/vyper/venom/passes/algebraic_optimization.py b/vyper/venom/passes/algebraic_optimization.py
index 0055e16e82..c558ba742e 100644
--- a/vyper/venom/passes/algebraic_optimization.py
+++ b/vyper/venom/passes/algebraic_optimization.py
@@ -348,18 +348,13 @@ def _optimize_comparator_instruction(self, inst, prefer_iszero):
             almost_always, never = hi, lo
             almost_never = lo + 1
 
-        if not unsigned:
-            almost_never = signed_to_unsigned(almost_never, 256, strict=True)
-            almost_always = signed_to_unsigned(almost_always, 256, strict=True)
-            never = signed_to_unsigned(never, 256, strict=True)
-
-        if lit_eq(operands[0], almost_never):
+        if lit_eq(operands[0], almost_never, unsigned):
             # (lt x 1), (gt x (MAX_UINT256 - 1)), (slt x (MIN_INT256 + 1))
             self.updater._update(inst, "eq", [operands[1], IRLiteral(never)])
             return
 
         # rewrites. in positions where iszero is preferred, (gt x 5) => (ge x 6)
-        if prefer_iszero and lit_eq(operands[0], almost_always):
+        if prefer_iszero and lit_eq(operands[0], almost_always, unsigned):
             # e.g. gt x 0, slt x MAX_INT256
             tmp = self.updater._add_before(inst, "eq", operands)
             self.updater._update(inst, "iszero", [tmp])
@@ -368,7 +363,7 @@ def _optimize_comparator_instruction(self, inst, prefer_iszero):
         # since push0 was introduced in shanghai, it's potentially
         # better to actually reverse this optimization -- i.e.
         # replace iszero(iszero(x)) with (gt x 0)
-        if opcode == "gt" and lit_eq(operands[0], 0):
+        if opcode == "gt" and lit_eq(operands[0], 0, unsigned):
             tmp = self.updater._add_before(inst, "iszero", [operands[1]])
             self.updater._update(inst, "iszero", [tmp])
             return
@@ -405,13 +400,10 @@ def _rewrite_ge_le(self, inst: IRInstruction):
             val -= 1
         new_opcode = _flip_comparison_op(opcode)
 
-        if not unsigned:
-            val = signed_to_unsigned(val, 256)
-
         # this can happen for cases like `lt x 0` which get reduced in SCCP.
         # don't handle them here, just return
         # unsigned is true since we already converted it if needed
-        if _wrap256(val, unsigned=True) != val:
+        if _wrap256(val, unsigned) != val:
             return
 
         self.updater._update(inst, new_opcode, [IRLiteral(val), operands[1]])
diff --git a/vyper/venom/passes/sccp/eval.py b/vyper/venom/passes/sccp/eval.py
index 7af7931c86..d5ed7fb0c8 100644
--- a/vyper/venom/passes/sccp/eval.py
+++ b/vyper/venom/passes/sccp/eval.py
@@ -14,7 +14,9 @@
 from vyper.venom.basicblock import IRLiteral, IROperand
 
 
-def lit_eq(op: IROperand, val: int) -> bool:
+def lit_eq(op: IROperand, val: int, unsigned: bool = True) -> bool:
+    if not unsigned:
+        return isinstance(op, IRLiteral) and _unsigned_to_signed(op.value) == val
     return isinstance(op, IRLiteral) and op.value == val