diff --git a/crates/vm/src/buffer.rs b/crates/vm/src/buffer.rs
index 4f23e16c5..e9c557ad1 100644
--- a/crates/vm/src/buffer.rs
+++ b/crates/vm/src/buffer.rs
@@ -1,6 +1,6 @@
 use crate::{
     AsObject, Py, PyObject, PyObjectRef, PyResult, TryFromObject, VirtualMachine,
-    builtins::{PyBaseExceptionRef, PyBytesRef, PyTuple, PyTupleRef, PyType, PyTypeRef},
+    builtins::{PyBaseExceptionRef, PyBytesRef, PyComplex, PyTuple, PyTupleRef, PyType, PyTypeRef},
     common::{static_cell, str::wchar_t},
     convert::ToPyObject,
     exceptions,
@@ -780,7 +780,7 @@ struct PackFloatComplex(f32, f32);
 struct PackDoubleComplex(f64, f64);
 
 macro_rules! make_pack_complex {
-    ($T:ty, $Elem:ty, $Bits:ty) => {
+    ($T:ty, $Elem:ty, $Bits:ty, $fmt:literal) => {
         impl Packable for $T {
             fn pack<E: ByteOrder>(
                 vm: &VirtualMachine,
@@ -788,20 +788,37 @@ macro_rules! make_pack_complex {
                 arg: PyObjectRef,
                 data: &mut [u8],
             ) -> Result<(), PackError> {
-                let c = ArgIntoComplex::try_from_object(vm, arg)
-                    .map_err(|_| {
-                        PackError::new(
-                            PackErrorKind::Type,
-                            vm,
-                            "required argument is not a complex",
-                        )
-                    })?
-                    .into_complex();
-                let half = size_of::<$Elem>();
-                (c.re as $Elem).to_bits().pack_int::<E>(&mut data[..half]);
-                (c.im as $Elem)
-                    .to_bits()
-                    .pack_int::<E>(&mut data[half..half * 2]);
+                let c = if let Some(value) = arg.downcast_ref::<PyComplex>() {
+                    value.to_complex()
+                } else {
+                    ArgIntoComplex::try_from_object(vm, arg)
+                        .map_err(|_| {
+                            PackError::new(
+                                PackErrorKind::Type,
+                                vm,
+                                "required argument is not a complex",
+                            )
+                        })?
+                        .into_complex()
+                };
+                for (component, bytes) in [c.re, c.im]
+                    .into_iter()
+                    .zip(data.chunks_exact_mut(size_of::<$Elem>()))
+                {
+                    let narrowed = component as $Elem;
+                    // CPython uses native casts for matching-endian complex formats.
+                    if E::convert(1u16) != 1 && narrowed.is_infinite() != component.is_infinite() {
+                        return Err(PackError {
+                            kind: PackErrorKind::Value,
+                            exception: vm.new_overflow_error(concat!(
+                                "float too large to pack with ",
+                                $fmt,
+                                " format"
+                            )),
+                        });
+                    }
+                    narrowed.to_bits().pack_int::<E>(bytes);
+                }
                 Ok(())
             }
 
@@ -815,8 +832,8 @@ macro_rules! make_pack_complex {
     };
 }
 
-make_pack_complex!(PackFloatComplex, f32, u32);
-make_pack_complex!(PackDoubleComplex, f64, u64);
+make_pack_complex!(PackFloatComplex, f32, u32, "f");
+make_pack_complex!(PackDoubleComplex, f64, u64, "d");
 
 impl Packable for f16 {
     fn pack<E: ByteOrder>(
diff --git a/crates/vm/src/builtins/complex.rs b/crates/vm/src/builtins/complex.rs
index 3f551a787..86c72d5f6 100644
--- a/crates/vm/src/builtins/complex.rs
+++ b/crates/vm/src/builtins/complex.rs
@@ -94,7 +94,9 @@ impl PyObjectRef {
             let result = method?.call((), vm)?;
 
             let ret_class = result.class().to_owned();
-            if let Some(ret) = result.downcast_ref::<PyComplex>() {
+            if let Some(ret) = result.downcast_ref::<PyComplex>()
+                && !result.class().is(vm.ctx.types.complex_type)
+            {
                 _warnings::warn(
                     vm.ctx.exceptions.deprecation_warning,
                     format!(
diff --git a/extra_tests/snippets/stdlib_struct_complex.py b/extra_tests/snippets/stdlib_struct_complex.py
new file mode 100644
index 000000000..b8ce52aca
--- /dev/null
+++ b/extra_tests/snippets/stdlib_struct_complex.py
@@ -0,0 +1,30 @@
+import struct
+import sys
+import warnings
+
+from testutils import assert_raises
+
+
+class ComplexLike:
+    def __complex__(self):
+        return 1 + 2j
+
+
+class ComplexSubclass(complex):
+    def __complex__(self):
+        raise AssertionError("complex subclasses use their stored value")
+
+
+with warnings.catch_warnings():
+    warnings.simplefilter("error")
+    for code in ("F", "D"):
+        expected = struct.pack(code, 1 + 2j)
+        assert struct.pack(code, ComplexLike()) == expected
+        assert struct.pack(code, ComplexSubclass(1, 2)) == expected
+
+native = "<" if sys.byteorder == "little" else ">"
+swapped = ">" if sys.byteorder == "little" else "<"
+for value in (complex(1e300, 0), complex(0, 1e300)):
+    assert struct.pack(native + "F", value) == struct.pack("@F", value)
+    with assert_raises(OverflowError):
+        struct.pack(swapped + "F", value)