diff --git a/crates/ruff_linter/resources/test/fixtures/pylint/iteration_over_set.py b/crates/ruff_linter/resources/test/fixtures/pylint/iteration_over_set.py
index f8d32e59a572b1..ae8ccb35133903 100644
--- a/crates/ruff_linter/resources/test/fixtures/pylint/iteration_over_set.py
+++ b/crates/ruff_linter/resources/test/fixtures/pylint/iteration_over_set.py
@@ -60,3 +60,6 @@
 for item in {1, 2, 2}:  # duplicate literals will be ignored
     # B033 catches this
     print(f"I like {item}.")
+
+for item in {False, 0, 0.0, 0j, True, 1, 1.0}:
+    print(item)
diff --git a/crates/ruff_linter/src/rules/pylint/rules/iteration_over_set.rs b/crates/ruff_linter/src/rules/pylint/rules/iteration_over_set.rs
index 0abc2d89b0e5a5..88c8afd56d4766 100644
--- a/crates/ruff_linter/src/rules/pylint/rules/iteration_over_set.rs
+++ b/crates/ruff_linter/src/rules/pylint/rules/iteration_over_set.rs
@@ -1,8 +1,10 @@
+use rustc_hash::{FxBuildHasher, FxHashSet};
+
 use ruff_diagnostics::{AlwaysFixableViolation, Diagnostic, Edit, Fix};
 use ruff_macros::{derive_message_formats, violation};
-use ruff_python_ast::{comparable::ComparableExpr, Expr};
+use ruff_python_ast::hashable::HashComparableExpr;
+use ruff_python_ast::Expr;
 use ruff_text_size::Ranged;
-use rustc_hash::{FxBuildHasher, FxHashSet};
 
 use crate::checkers::ast::Checker;
 
@@ -54,8 +56,7 @@ pub(crate) fn iteration_over_set(checker: &mut Checker, expr: &Expr) {
 
     let mut seen_values = FxHashSet::with_capacity_and_hasher(set.len(), FxBuildHasher);
     for value in set {
-        let comparable_value = ComparableExpr::from(value);
-        if !seen_values.insert(comparable_value) {
+        if !seen_values.insert(HashComparableExpr::from(value)) {
             // if the set contains a duplicate literal value, early exit.
             // rule `B033` can catch that.
             return;
diff --git a/crates/ruff_python_ast/src/comparable.rs b/crates/ruff_python_ast/src/comparable.rs
index a6825b6eb2578c..421c7363d1c938 100644
--- a/crates/ruff_python_ast/src/comparable.rs
+++ b/crates/ruff_python_ast/src/comparable.rs
@@ -861,8 +861,14 @@ pub struct ExprNumberLiteral<'a> {
 }
 
 #[derive(Debug, PartialEq, Eq, Hash)]
-pub struct ExprBoolLiteral<'a> {
-    value: &'a bool,
+pub struct ExprBoolLiteral {
+    value: bool,
+}
+
+impl From<bool> for ExprBoolLiteral {
+    fn from(value: bool) -> Self {
+        Self { value }
+    }
 }
 
 #[derive(Debug, PartialEq, Eq, Hash)]
@@ -934,7 +940,7 @@ pub enum ComparableExpr<'a> {
     StringLiteral(ExprStringLiteral<'a>),
     BytesLiteral(ExprBytesLiteral<'a>),
     NumberLiteral(ExprNumberLiteral<'a>),
-    BoolLiteral(ExprBoolLiteral<'a>),
+    BoolLiteral(ExprBoolLiteral),
     NoneLiteral,
     EllipsisLiteral,
     Attribute(ExprAttribute<'a>),
@@ -1109,7 +1115,7 @@ impl<'a> From<&'a ast::Expr> for ComparableExpr<'a> {
                 })
             }
             ast::Expr::BooleanLiteral(ast::ExprBooleanLiteral { value, range: _ }) => {
-                Self::BoolLiteral(ExprBoolLiteral { value })
+                Self::BoolLiteral(ExprBoolLiteral { value: *value })
             }
             ast::Expr::NoneLiteral(_) => Self::NoneLiteral,
             ast::Expr::EllipsisLiteral(_) => Self::EllipsisLiteral,
diff --git a/crates/ruff_python_ast/src/hashable.rs b/crates/ruff_python_ast/src/hashable.rs
new file mode 100644
index 00000000000000..2ca7b534ac6ec8
--- /dev/null
+++ b/crates/ruff_python_ast/src/hashable.rs
@@ -0,0 +1,65 @@
+use std::hash::Hash;
+
+use crate::{Expr, Number};
+
+use crate::comparable::{ComparableExpr, ExprBoolLiteral};
+
+/// Wrapper around [`Expr`] that implements [`Hash`] and [`PartialEq`] according to Python
+/// semantics:
+///
+/// > Values that compare equal (such as 1, 1.0, and True) can be used interchangeably to index the
+/// > same dictionary entry.
+///
+/// For example, considers `True`, `1`, and `1.0` to be equal, as they hash to the same value
+/// in Python, along with `False`, `0`, and `0.0`.
+///
+/// See: <https://docs.python.org/3/library/stdtypes.html#mapping-types-dict>
+pub struct HashComparableExpr<'a>(ComparableExpr<'a>);
+
+impl Hash for HashComparableExpr<'_> {
+    fn hash<H: std::hash::Hasher>(&self, state: &mut H) {
+        self.0.hash(state);
+    }
+}
+
+impl PartialEq<Self> for HashComparableExpr<'_> {
+    fn eq(&self, other: &Self) -> bool {
+        self.0 == other.0
+    }
+}
+
+impl Eq for HashComparableExpr<'_> {}
+
+impl<'a> From<&'a Expr> for HashComparableExpr<'a> {
+    fn from(expr: &'a Expr) -> Self {
+        as_bool(expr)
+            .map(ExprBoolLiteral::from)
+            .map(ComparableExpr::BoolLiteral)
+            .map(Self)
+            .unwrap_or_else(|| Self(ComparableExpr::from(expr)))
+    }
+}
+
+/// Returns the `bool` value of the given expression, if it has an equivalent hash to `True` or `False`.
+fn as_bool(expr: &Expr) -> Option<bool> {
+    let Expr::NumberLiteral(expr) = expr else {
+        return None;
+    };
+    match &expr.value {
+        Number::Int(int) => match int.as_u8() {
+            Some(0) => Some(false),
+            Some(1) => Some(true),
+            _ => None,
+        },
+        Number::Float(float) => match float {
+            0.0 => Some(false),
+            1.0 => Some(true),
+            _ => None,
+        },
+        Number::Complex { real, imag } => match (real, imag) {
+            (0.0, 0.0) => Some(false),
+            (1.0, 0.0) => Some(true),
+            _ => None,
+        },
+    }
+}
diff --git a/crates/ruff_python_ast/src/lib.rs b/crates/ruff_python_ast/src/lib.rs
index 53c3a72db834b4..b149bdddc8430b 100644
--- a/crates/ruff_python_ast/src/lib.rs
+++ b/crates/ruff_python_ast/src/lib.rs
@@ -9,6 +9,7 @@ pub use nodes::*;
 pub mod comparable;
 pub mod docstrings;
 mod expression;
+pub mod hashable;
 pub mod helpers;
 pub mod identifier;
 mod int;