diff --git a/crates/aiken-lang/src/air.rs b/crates/aiken-lang/src/air.rs
index 1c063406..42808933 100644
--- a/crates/aiken-lang/src/air.rs
+++ b/crates/aiken-lang/src/air.rs
@@ -117,6 +117,11 @@ pub enum Air {
         constr_index: usize,
     },
 
+    AssertBool {
+        scope: Vec<u64>,
+        is_true: bool,
+    },
+
     // When
     When {
         scope: Vec<u64>,
@@ -268,6 +273,7 @@ impl Air {
             | Air::UnWrapData { scope, .. }
             | Air::WrapData { scope, .. }
             | Air::AssertConstr { scope, .. }
+            | Air::AssertBool { scope, .. }
             | Air::When { scope, .. }
             | Air::Clause { scope, .. }
             | Air::ListClause { scope, .. }
@@ -375,6 +381,7 @@ impl Air {
             | Air::Let { .. }
             | Air::WrapClause { .. }
             | Air::AssertConstr { .. }
+            | Air::AssertBool { .. }
             | Air::Finally { .. }
             | Air::FieldsExpose { .. } => None,
 
diff --git a/crates/aiken-lang/src/uplc.rs b/crates/aiken-lang/src/uplc.rs
index cd740474..6dacf291 100644
--- a/crates/aiken-lang/src/uplc.rs
+++ b/crates/aiken-lang/src/uplc.rs
@@ -2056,66 +2056,78 @@ impl<'a> CodeGenerator<'a> {
                         scope: scope.clone(),
                         check_last_item: false,
                     });
-                } else {
+                } else if !tipo.is_bool() {
                     pattern_vec.push(Air::Let {
                         scope: scope.clone(),
                         name: "_".to_string(),
                     });
                 }
 
-                if matches!(assignment_properties.kind, AssignmentKind::Expect) {
-                    let data_type =
-                        lookup_data_type_by_tipo(self.data_types.clone(), tipo).unwrap();
+                match assignment_properties.kind {
+                    AssignmentKind::Let => {
+                        pattern_vec.append(values);
+                    }
+                    AssignmentKind::Expect => {
+                        if tipo.is_bool() {
+                            pattern_vec.push(Air::AssertBool {
+                                scope,
+                                is_true: constr_name == "True",
+                            });
 
-                    let (index, _) = data_type
-                        .constructors
-                        .iter()
-                        .enumerate()
-                        .find(|(_, constr)| &constr.name == constr_name)
-                        .unwrap();
+                            pattern_vec.append(values);
+                        } else {
+                            let data_type =
+                                lookup_data_type_by_tipo(self.data_types.clone(), tipo).unwrap();
 
-                    let constr_name = format!("__{}_{}", constr_name, self.id_gen.next());
+                            let (index, _) = data_type
+                                .constructors
+                                .iter()
+                                .enumerate()
+                                .find(|(_, constr)| &constr.name == constr_name)
+                                .unwrap();
 
-                    pattern_vec.push(Air::Let {
-                        scope: scope.clone(),
-                        name: constr_name.clone(),
-                    });
+                            let constr_name = format!("__{}_{}", constr_name, self.id_gen.next());
 
-                    pattern_vec.append(values);
+                            pattern_vec.push(Air::Let {
+                                scope: scope.clone(),
+                                name: constr_name.clone(),
+                            });
 
-                    let mut scope = scope;
-                    scope.push(self.id_gen.next());
+                            pattern_vec.append(values);
 
-                    pattern_vec.push(Air::AssertConstr {
-                        scope: scope.clone(),
-                        constr_index: index,
-                    });
+                            let mut scope = scope;
+                            scope.push(self.id_gen.next());
 
-                    pattern_vec.push(Air::Var {
-                        scope: scope.clone(),
-                        constructor: ValueConstructor::public(
-                            tipo.clone().into(),
-                            ValueConstructorVariant::LocalVariable {
-                                location: Span::empty(),
-                            },
-                        ),
-                        name: constr_name.clone(),
-                        variant_name: String::new(),
-                    });
+                            pattern_vec.push(Air::AssertConstr {
+                                scope: scope.clone(),
+                                constr_index: index,
+                            });
 
-                    pattern_vec.push(Air::Var {
-                        scope,
-                        constructor: ValueConstructor::public(
-                            tipo.clone().into(),
-                            ValueConstructorVariant::LocalVariable {
-                                location: Span::empty(),
-                            },
-                        ),
-                        name: constr_name,
-                        variant_name: String::new(),
-                    });
-                } else {
-                    pattern_vec.append(values);
+                            pattern_vec.push(Air::Var {
+                                scope: scope.clone(),
+                                constructor: ValueConstructor::public(
+                                    tipo.clone().into(),
+                                    ValueConstructorVariant::LocalVariable {
+                                        location: Span::empty(),
+                                    },
+                                ),
+                                name: constr_name.clone(),
+                                variant_name: String::new(),
+                            });
+
+                            pattern_vec.push(Air::Var {
+                                scope,
+                                constructor: ValueConstructor::public(
+                                    tipo.clone().into(),
+                                    ValueConstructorVariant::LocalVariable {
+                                        location: Span::empty(),
+                                    },
+                                ),
+                                name: constr_name,
+                                variant_name: String::new(),
+                            });
+                        }
+                    }
                 }
 
                 pattern_vec.append(&mut nested_pattern);
@@ -4843,7 +4855,7 @@ impl<'a> CodeGenerator<'a> {
                         Term::Builtin(DefaultFunction::Trace).force_wrap(),
                         Term::Constant(
                             UplcConstant::String(
-                                "Asserted on incorrect constructor variant.".to_string(),
+                                "Expected on incorrect constructor variant.".to_string(),
                             )
                             .into(),
                         ),
@@ -4866,6 +4878,31 @@ impl<'a> CodeGenerator<'a> {
 
                 arg_stack.push(term);
             }
+            Air::AssertBool { is_true, .. } => {
+                let value = arg_stack.pop().unwrap();
+                let mut term = arg_stack.pop().unwrap();
+
+                let error_term = apply_wrap(
+                    apply_wrap(
+                        Term::Builtin(DefaultFunction::Trace).force_wrap(),
+                        Term::Constant(
+                            UplcConstant::String(
+                                "Expected on incorrect boolean variant.".to_string(),
+                            )
+                            .into(),
+                        ),
+                    ),
+                    Term::Delay(Term::Error.into()),
+                )
+                .force_wrap();
+
+                if is_true {
+                    term = delayed_if_else(value, term, error_term);
+                } else {
+                    term = delayed_if_else(value, error_term, term);
+                }
+                arg_stack.push(term);
+            }
             Air::When {
                 subject_name, tipo, ..
             } => {
diff --git a/examples/acceptance_tests/071/plutus.json b/examples/acceptance_tests/071/plutus.json
index 114b3c20..0cd2e1b3 100644
--- a/examples/acceptance_tests/071/plutus.json
+++ b/examples/acceptance_tests/071/plutus.json
@@ -164,8 +164,8 @@
           ]
         }
       },
-      "compiledCode": "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",
-      "hash": "c95b3842362b77afec21773b7c0b1f09e61bf5e4c58b685533e6d342"
+      "compiledCode": "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",
+      "hash": "b79dffa847f2b9a55cb6cee2bd6057251f45e6a252587c7f6f3545d0"
     }
   ]
 }
\ No newline at end of file
diff --git a/examples/acceptance_tests/076/aiken.lock b/examples/acceptance_tests/076/aiken.lock
new file mode 100644
index 00000000..3a78b1e7
--- /dev/null
+++ b/examples/acceptance_tests/076/aiken.lock
@@ -0,0 +1,5 @@
+# This file was generated by Aiken
+# You typically do not need to edit this file
+
+requirements = []
+packages = []
diff --git a/examples/acceptance_tests/076/aiken.toml b/examples/acceptance_tests/076/aiken.toml
new file mode 100644
index 00000000..2de1a654
--- /dev/null
+++ b/examples/acceptance_tests/076/aiken.toml
@@ -0,0 +1,3 @@
+name = 'aiken-lang/acceptance_test_076'
+version = '0.0.0'
+description = ''
diff --git a/examples/acceptance_tests/076/lib/tests.ak b/examples/acceptance_tests/076/lib/tests.ak
new file mode 100644
index 00000000..983662d8
--- /dev/null
+++ b/examples/acceptance_tests/076/lib/tests.ak
@@ -0,0 +1,5 @@
+test expect_positive() {
+  let val = 5
+  expect True = val > 0
+  True
+}