diff --git a/resources/test/fixtures/flake8_annotations/allow_overload.py b/resources/test/fixtures/flake8_annotations/allow_overload.py
new file mode 100644
index 0000000000..72d4ee3cff
--- /dev/null
+++ b/resources/test/fixtures/flake8_annotations/allow_overload.py
@@ -0,0 +1,49 @@
+from typing import overload
+
+
+@overload
+def foo(i: int) -> "int":
+    ...
+
+
+@overload
+def foo(i: "str") -> "str":
+    ...
+
+
+def foo(i):
+    return i
+
+
+@overload
+def bar(i: int) -> "int":
+    ...
+
+
+@overload
+def bar(i: "str") -> "str":
+    ...
+
+
+class X:
+    def bar(i):
+        return i
+
+
+# TODO(charlie): This third case should raise an error (as in Mypy), because we have a
+# statement between the interfaces and implementation.
+@overload
+def baz(i: int) -> "int":
+    ...
+
+
+@overload
+def baz(i: "str") -> "str":
+    ...
+
+
+x = 1
+
+
+def baz(i):
+    return i
diff --git a/src/check_ast.rs b/src/check_ast.rs
index fb66ec4f92..2a4eb8c05a 100644
--- a/src/check_ast.rs
+++ b/src/check_ast.rs
@@ -3132,6 +3132,8 @@ impl<'a> Checker<'a> {
     }
 
     fn check_definitions(&mut self) {
+        let mut overloaded_name: Option<String> = None;
+        self.definitions.reverse();
         while let Some((definition, visibility)) = self.definitions.pop() {
             // flake8-annotations
             if self.settings.enabled.contains(&CheckCode::ANN001)
@@ -3146,7 +3148,21 @@ impl<'a> Checker<'a> {
                 || self.settings.enabled.contains(&CheckCode::ANN206)
                 || self.settings.enabled.contains(&CheckCode::ANN401)
             {
-                flake8_annotations::plugins::definition(self, &definition, &visibility);
+                // TODO(charlie): This should be even stricter, in that an overload
+                // implementation should come immediately after the overloaded
+                // interfaces, without any AST nodes in between. Right now, we
+                // only error when traversing definition boundaries (functions,
+                // classes, etc.).
+                if !overloaded_name.map_or(false, |overloaded_name| {
+                    flake8_annotations::helpers::is_overload_impl(
+                        self,
+                        &definition,
+                        &overloaded_name,
+                    )
+                }) {
+                    flake8_annotations::plugins::definition(self, &definition, &visibility);
+                }
+                overloaded_name = flake8_annotations::helpers::overloaded_name(self, &definition);
             }
 
             // pydocstyle
diff --git a/src/flake8_annotations/helpers.rs b/src/flake8_annotations/helpers.rs
new file mode 100644
index 0000000000..1e2ae2f86e
--- /dev/null
+++ b/src/flake8_annotations/helpers.rs
@@ -0,0 +1,62 @@
+use rustpython_ast::{Arguments, Expr, Stmt, StmtKind};
+
+use crate::check_ast::Checker;
+use crate::docstrings::definition::{Definition, DefinitionKind};
+use crate::visibility;
+
+pub(super) fn match_function_def(
+    stmt: &Stmt,
+) -> (&str, &Arguments, &Option<Box<Expr>>, &Vec<Stmt>) {
+    match &stmt.node {
+        StmtKind::FunctionDef {
+            name,
+            args,
+            returns,
+            body,
+            ..
+        }
+        | StmtKind::AsyncFunctionDef {
+            name,
+            args,
+            returns,
+            body,
+            ..
+        } => (name, args, returns, body),
+        _ => panic!("Found non-FunctionDef in match_name"),
+    }
+}
+
+/// Return the name of the function, if it's overloaded.
+pub fn overloaded_name(checker: &Checker, definition: &Definition) -> Option<String> {
+    if let DefinitionKind::Function(stmt)
+    | DefinitionKind::NestedFunction(stmt)
+    | DefinitionKind::Method(stmt) = definition.kind
+    {
+        if visibility::is_overload(checker, stmt) {
+            let (name, ..) = match_function_def(stmt);
+            Some(name.to_string())
+        } else {
+            None
+        }
+    } else {
+        None
+    }
+}
+
+/// Return `true` if the definition is the implementation for an overloaded
+/// function.
+pub fn is_overload_impl(checker: &Checker, definition: &Definition, overloaded_name: &str) -> bool {
+    if let DefinitionKind::Function(stmt)
+    | DefinitionKind::NestedFunction(stmt)
+    | DefinitionKind::Method(stmt) = definition.kind
+    {
+        if visibility::is_overload(checker, stmt) {
+            false
+        } else {
+            let (name, ..) = match_function_def(stmt);
+            name == overloaded_name
+        }
+    } else {
+        false
+    }
+}
diff --git a/src/flake8_annotations/mod.rs b/src/flake8_annotations/mod.rs
index 56f92b217e..6110cd1526 100644
--- a/src/flake8_annotations/mod.rs
+++ b/src/flake8_annotations/mod.rs
@@ -1,3 +1,4 @@
+pub mod helpers;
 pub mod plugins;
 pub mod settings;
 
@@ -134,4 +135,24 @@ mod tests {
         insta::assert_yaml_snapshot!(checks);
         Ok(())
     }
+
+    #[test]
+    fn allow_overload() -> Result<()> {
+        let mut checks = test_path(
+            Path::new("./resources/test/fixtures/flake8_annotations/allow_overload.py"),
+            &Settings {
+                ..Settings::for_rules(vec![
+                    CheckCode::ANN201,
+                    CheckCode::ANN202,
+                    CheckCode::ANN204,
+                    CheckCode::ANN205,
+                    CheckCode::ANN206,
+                ])
+            },
+            true,
+        )?;
+        checks.sort_by_key(|check| check.location);
+        insta::assert_yaml_snapshot!(checks);
+        Ok(())
+    }
 }
diff --git a/src/flake8_annotations/plugins.rs b/src/flake8_annotations/plugins.rs
index afd05d4cbe..fb5018bd16 100644
--- a/src/flake8_annotations/plugins.rs
+++ b/src/flake8_annotations/plugins.rs
@@ -1,4 +1,4 @@
-use rustpython_ast::{Arguments, Constant, Expr, ExprKind, Stmt, StmtKind};
+use rustpython_ast::{Constant, Expr, ExprKind, Stmt, StmtKind};
 
 use crate::ast::types::Range;
 use crate::ast::visitor;
@@ -6,6 +6,7 @@ use crate::ast::visitor::Visitor;
 use crate::check_ast::Checker;
 use crate::checks::{CheckCode, CheckKind};
 use crate::docstrings::definition::{Definition, DefinitionKind};
+use crate::flake8_annotations::helpers::match_function_def;
 use crate::visibility::Visibility;
 use crate::{visibility, Check};
 
@@ -61,26 +62,6 @@ where
     };
 }
 
-fn match_function_def(stmt: &Stmt) -> (&str, &Arguments, &Option<Box<Expr>>, &Vec<Stmt>) {
-    match &stmt.node {
-        StmtKind::FunctionDef {
-            name,
-            args,
-            returns,
-            body,
-            ..
-        }
-        | StmtKind::AsyncFunctionDef {
-            name,
-            args,
-            returns,
-            body,
-            ..
-        } => (name, args, returns, body),
-        _ => panic!("Found non-FunctionDef in match_name"),
-    }
-}
-
 /// Generate flake8-annotation checks for a given `Definition`.
 pub fn definition(checker: &mut Checker, definition: &Definition, visibility: &Visibility) {
     // TODO(charlie): Consider using the AST directly here rather than `Definition`.
diff --git a/src/flake8_annotations/snapshots/ruff__flake8_annotations__tests__allow_overload.snap b/src/flake8_annotations/snapshots/ruff__flake8_annotations__tests__allow_overload.snap
new file mode 100644
index 0000000000..de6ed83da2
--- /dev/null
+++ b/src/flake8_annotations/snapshots/ruff__flake8_annotations__tests__allow_overload.snap
@@ -0,0 +1,14 @@
+---
+source: src/flake8_annotations/mod.rs
+expression: checks
+---
+- kind:
+    MissingReturnTypePublicFunction: bar
+  location:
+    row: 29
+    column: 4
+  end_location:
+    row: 35
+    column: 0
+  fix: ~
+