diff --git a/compiler/noirc_evaluator/src/ssa/ir/dfg/simplify/constrain.rs b/compiler/noirc_evaluator/src/ssa/ir/dfg/simplify/constrain.rs
index f88bdd183b0..d769f7e2aed 100644
--- a/compiler/noirc_evaluator/src/ssa/ir/dfg/simplify/constrain.rs
+++ b/compiler/noirc_evaluator/src/ssa/ir/dfg/simplify/constrain.rs
@@ -159,7 +159,7 @@ pub(super) fn decompose_constrain(
                     Instruction::Cast(val, _) => {
                         let original_typ = dfg.type_of_value(val).unwrap_numeric();
                         let original_typ_max_value =
-                            original_typ.max_value().map(|max_value| *constant < max_value);
+                            original_typ.max_value().map(|max_value| *constant <= max_value);
 
                         match original_typ_max_value {
                             Ok(true) => {
@@ -280,4 +280,155 @@ mod tests {
         }
         ");
     }
+
+    #[test]
+    fn decompose_not_condition() {
+        let src_template = "
+            acir(inline) fn main f0 {
+              b0(v0: u1):
+                v1 = not v0
+                constrain v1 == u1 {}
+                return
+            }
+            ";
+
+        let src = src_template.replace("{}", "1");
+        let ssa = Ssa::from_str_simplifying(&src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u1):
+            v1 = not v0
+            constrain v0 == u1 0
+            return
+        }
+        ");
+
+        let src = src_template.replace("{}", "0");
+        let ssa = Ssa::from_str_simplifying(&src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u1):
+            v1 = not v0
+            constrain v0 == u1 1
+            return
+        }
+        ");
+    }
+
+    #[test]
+    fn decompose_or_condition() {
+        let src = "
+            acir(inline) fn main f0 {
+              b0(v0: u8, v1: u8):
+                v2 = or v0, v1
+                constrain v2 == u1 0
+                return
+            }
+            ";
+        let ssa = Ssa::from_str_simplifying(src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u8, v1: u8):
+            v2 = or v0, v1
+            constrain v0 == u8 0
+            constrain v1 == u8 0
+            return
+        }
+        ");
+    }
+
+    #[test]
+    fn remove_casts_from_same_type() {
+        let src = "
+            acir(inline) fn main f0 {
+              b0(v0: u1, v1: u1):
+                v2 = cast v0 as u8
+                v3 = cast v1 as u8
+                constrain v2 == v3
+                return
+            }
+            ";
+        let ssa = Ssa::from_str_simplifying(src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u1, v1: u1):
+            v2 = cast v0 as u8
+            v3 = cast v1 as u8
+            constrain v0 == v1
+            return
+        }
+        ");
+    }
+
+    #[test]
+    fn does_not_remove_casts_from_different_types() {
+        let src = "
+            acir(inline) fn main f0 {
+              b0(v0: u1, v1: u8):
+                v2 = cast v0 as u16
+                v3 = cast v1 as u16
+                constrain v2 == v3
+                return
+            }
+            ";
+        let ssa = Ssa::from_str_simplifying(src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u1, v1: u8):
+            v2 = cast v0 as u16
+            v3 = cast v1 as u16
+            constrain v2 == v3
+            return
+        }
+        ");
+    }
+
+    #[test]
+    fn replaces_constants_with_pre_cast_type() {
+        let src = "
+            acir(inline) fn main f0 {
+              b0(v0: u8):
+                v1 = cast v0 as u16
+                constrain v1 == u16 255
+                return
+            }
+            ";
+        let ssa = Ssa::from_str_simplifying(src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u8):
+            v1 = cast v0 as u16
+            constrain v0 == u8 255
+            return
+        }
+        ");
+    }
+
+    #[test]
+    fn does_not_cast_constant_to_incompatible_type() {
+        let src = "
+            acir(inline) fn main f0 {
+              b0(v0: u8):
+                v1 = cast v0 as u16
+                constrain v1 == u16 256
+                return
+            }
+            ";
+        let ssa = Ssa::from_str_simplifying(src).unwrap();
+
+        assert_ssa_snapshot!(ssa, @r"
+        acir(inline) fn main f0 {
+          b0(v0: u8):
+            v1 = cast v0 as u16
+            constrain v1 == u16 256
+            return
+        }
+        ");
+    }
 }