diff --git a/simulator/generation/predicate/unary.rs b/simulator/generation/predicate/unary.rs
index 7e8a72bc5..9a712ba55 100644
--- a/simulator/generation/predicate/unary.rs
+++ b/simulator/generation/predicate/unary.rs
@@ -1,17 +1,53 @@
 //! Contains code for generation for [ast::Expr::Unary] Predicate
+//! TODO: for now just generating [ast::Literal], but want to also generate Columns and any
+//! arbitrary [ast::Expr]
 
+use limbo_core::numeric::NullableInteger;
 use limbo_sqlite3_parser::ast::{self, Expr};
 
 use crate::{
-    generation::{
-        backtrack, pick, predicate::SimplePredicate, ArbitraryFrom as _, ArbitraryFromMaybe,
-    },
+    generation::{backtrack, pick, predicate::SimplePredicate, ArbitraryFromMaybe},
     model::{
         query::predicate::Predicate,
         table::{Table, Value},
     },
 };
 
+// NullableInteger Code copied from Core. Ideally we should use Limbo's Core Value for everything to avoid code repetition
+impl From<NullableInteger> for Value {
+    fn from(value: NullableInteger) -> Self {
+        match value {
+            NullableInteger::Null => Value::Null,
+            NullableInteger::Integer(v) => Value::Integer(v),
+        }
+    }
+}
+
+impl From<Value> for NullableInteger {
+    fn from(value: Value) -> Self {
+        Self::from(&value)
+    }
+}
+
+impl From<&Value> for NullableInteger {
+    fn from(value: &Value) -> Self {
+        match value {
+            Value::Null => Self::Null,
+            Value::Integer(v) => Self::Integer(*v),
+            Value::Float(v) => Self::Integer(*v as i64),
+            Value::Text(text) => Self::from(text.as_str()),
+            Value::Blob(blob) => {
+                let text = String::from_utf8_lossy(blob.as_slice());
+                Self::from(text)
+            }
+        }
+    }
+}
+
+fn exec_bit_not(reg: &Value) -> Value {
+    (!NullableInteger::from(reg)).into()
+}
+
 pub struct TrueValue(pub Value);
 
 impl ArbitraryFromMaybe<&Value> for TrueValue {
@@ -56,7 +92,7 @@ impl ArbitraryFromMaybe<&Vec<&Value>> for FalseValue {
         Self: Sized,
     {
         if values.is_empty() {
-            return Some(Self(Value::TRUE));
+            return Some(Self(Value::FALSE));
         }
 
         let value = pick(values, rng);
@@ -64,6 +100,39 @@ impl ArbitraryFromMaybe<&Vec<&Value>> for FalseValue {
     }
 }
 
+pub struct BitNotValue(pub Value);
+
+impl ArbitraryFromMaybe<(&Value, bool)> for BitNotValue {
+    fn arbitrary_from_maybe<R: rand::Rng>(
+        _rng: &mut R,
+        (value, predicate): (&Value, bool),
+    ) -> Option<Self>
+    where
+        Self: Sized,
+    {
+        let bit_not_val = exec_bit_not(value);
+        // If you bit not the Value and it meets the predicate return Some, else None
+        (bit_not_val.into_bool() == predicate).then_some(BitNotValue(value.clone()))
+    }
+}
+
+impl ArbitraryFromMaybe<(&Vec<&Value>, bool)> for BitNotValue {
+    fn arbitrary_from_maybe<R: rand::Rng>(
+        rng: &mut R,
+        (values, predicate): (&Vec<&Value>, bool),
+    ) -> Option<Self>
+    where
+        Self: Sized,
+    {
+        if values.is_empty() {
+            return None;
+        }
+
+        let value = pick(values, rng);
+        Self::arbitrary_from_maybe(rng, (*value, predicate))
+    }
+}
+
 impl SimplePredicate {
     /// Generates a true [ast::Expr::Unary] [SimplePredicate] from a [Table]
     pub fn true_unary<R: rand::Rng>(rng: &mut R, table: &Table, column_index: usize) -> Self {
@@ -87,11 +156,89 @@ impl SimplePredicate {
                 (
                     num_retries,
                     Box::new(|rng| {
-                        FalseValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                        TrueValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                            // True Value with negative is still True
                             Expr::unary(ast::UnaryOperator::Negative, Expr::Literal(value.0.into()))
                         })
                     }),
                 ),
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        BitNotValue::arbitrary_from_maybe(rng, (&column_values, true)).map(
+                            |value| {
+                                Expr::unary(
+                                    ast::UnaryOperator::BitwiseNot,
+                                    Expr::Literal(value.0.into()),
+                                )
+                            },
+                        )
+                    }),
+                ),
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        FalseValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                            Expr::unary(ast::UnaryOperator::Not, Expr::Literal(value.0.into()))
+                        })
+                    }),
+                ),
+            ],
+            rng,
+        );
+        // If cannot generate a value
+        SimplePredicate(Predicate(expr.unwrap_or(Expr::Literal(Value::TRUE.into()))))
+    }
+
+    /// Generates a false [ast::Expr::Unary] [SimplePredicate] from a [Table]
+    pub fn false_unary<R: rand::Rng>(rng: &mut R, table: &Table, column_index: usize) -> Self {
+        let column_values = table
+            .rows
+            .iter()
+            .map(|r| &r[column_index])
+            .collect::<Vec<_>>();
+        let num_retries = column_values.len();
+        let expr = backtrack(
+            vec![
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        FalseValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                            // Positive is a no-op in Sqlite
+                            Expr::unary(ast::UnaryOperator::Positive, Expr::Literal(value.0.into()))
+                        })
+                    }),
+                ),
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        FalseValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                            // True Value with negative is still True
+                            Expr::unary(ast::UnaryOperator::Negative, Expr::Literal(value.0.into()))
+                        })
+                    }),
+                ),
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        BitNotValue::arbitrary_from_maybe(rng, (&column_values, false)).map(
+                            |value| {
+                                Expr::unary(
+                                    ast::UnaryOperator::BitwiseNot,
+                                    Expr::Literal(value.0.into()),
+                                )
+                            },
+                        )
+                    }),
+                ),
+                (
+                    num_retries,
+                    Box::new(|rng| {
+                        TrueValue::arbitrary_from_maybe(rng, &column_values).map(|value| {
+                            Expr::unary(ast::UnaryOperator::Not, Expr::Literal(value.0.into()))
+                        })
+                    }),
+                ),
             ],
             rng,
         );