diff --git a/include/pybind11/cast.h b/include/pybind11/cast.h
index ce85d997b6..21f9adcade 100644
--- a/include/pybind11/cast.h
+++ b/include/pybind11/cast.h
@@ -1014,9 +1014,7 @@ template <typename CharT> using is_std_char_type = any_of<
 
 template <typename T>
 struct type_caster<T, enable_if_t<std::is_arithmetic<T>::value && !is_std_char_type<T>::value>> {
-    using _py_type_0 = conditional_t<sizeof(T) <= sizeof(long), long, long long>;
-    using _py_type_1 = conditional_t<std::is_signed<T>::value, _py_type_0, typename std::make_unsigned<_py_type_0>::type>;
-    using py_type = conditional_t<std::is_floating_point<T>::value, double, _py_type_1>;
+    using py_type = conditional_t<std::is_floating_point<T>::value, double, py_int_type_for<T>>;
 public:
 
     bool load(handle src, bool convert) {
@@ -1042,12 +1040,8 @@ struct type_caster<T, enable_if_t<std::is_arithmetic<T>::value && !is_std_char_t
             return false;
         } else if (!convert && !index_check(src.ptr()) && !PYBIND11_LONG_CHECK(src.ptr())) {
             return false;
-        } else if (std::is_unsigned<py_type>::value) {
-            py_value = as_unsigned<py_type>(src.ptr());
-        } else { // signed integer:
-            py_value = sizeof(T) <= sizeof(long)
-                ? (py_type) PyLong_AsLong(src.ptr())
-                : (py_type) PYBIND11_LONG_AS_LONGLONG(src.ptr());
+        } else {
+            py_value = as_integer<py_type>(src.ptr());
         }
 
         // Python API reported an error
diff --git a/include/pybind11/detail/common.h b/include/pybind11/detail/common.h
index cb05bd14d1..35d0c0ba83 100644
--- a/include/pybind11/detail/common.h
+++ b/include/pybind11/detail/common.h
@@ -175,6 +175,7 @@
 #define PYBIND11_BYTES_SIZE PyBytes_Size
 #define PYBIND11_LONG_CHECK(o) PyLong_Check(o)
 #define PYBIND11_LONG_AS_LONGLONG(o) PyLong_AsLongLong(o)
+#define PYBIND11_LONG_AS_UNSIGNED_LONGLONG(o) PyLong_AsUnsignedLongLong(o)
 #define PYBIND11_LONG_FROM_SIGNED(o) PyLong_FromSsize_t((ssize_t) o)
 #define PYBIND11_LONG_FROM_UNSIGNED(o) PyLong_FromSize_t((size_t) o)
 #define PYBIND11_BYTES_NAME "bytes"
@@ -203,6 +204,7 @@
 #define PYBIND11_BYTES_SIZE PyString_Size
 #define PYBIND11_LONG_CHECK(o) (PyInt_Check(o) || PyLong_Check(o))
 #define PYBIND11_LONG_AS_LONGLONG(o) (PyInt_Check(o) ? (long long) PyLong_AsLong(o) : PyLong_AsLongLong(o))
+#define PYBIND11_LONG_AS_UNSIGNED_LONGLONG(o) (PyInt_Check(o) ? (unsigned long long) PyLong_AsUnsignedLong(o) : PyLong_AsUnsignedLongLong(o))
 #define PYBIND11_LONG_FROM_SIGNED(o) PyInt_FromSsize_t((ssize_t) o) // Returns long if needed.
 #define PYBIND11_LONG_FROM_UNSIGNED(o) PyInt_FromSize_t((size_t) o) // Returns long if needed.
 #define PYBIND11_BYTES_NAME "str"
diff --git a/include/pybind11/pytypes.h b/include/pybind11/pytypes.h
index d8d58b1d56..83264759a6 100644
--- a/include/pybind11/pytypes.h
+++ b/include/pybind11/pytypes.h
@@ -10,6 +10,7 @@
 #pragma once
 
 #include "detail/common.h"
+#include "detail/typeid.h"
 #include "buffer_info.h"
 #include <utility>
 #include <type_traits>
@@ -1091,23 +1092,37 @@ class bool_ : public object {
 };
 
 PYBIND11_NAMESPACE_BEGIN(detail)
+template <typename T>
+using py_signed_int_type_for = conditional_t<sizeof(T) <= sizeof(long), long, long long>;
+
+template <typename T>
+using py_unsigned_int_type_for = typename std::make_unsigned<py_signed_int_type_for<T>>::type;
+
+template <typename T>
+using py_int_type_for = conditional_t<std::is_signed<T>::value, py_signed_int_type_for<T>, py_unsigned_int_type_for<T>>;
+
 // Converts a value to the given unsigned type.  If an error occurs, you get back (Unsigned) -1;
 // otherwise you get back the unsigned long or unsigned long long value cast to (Unsigned).
 // (The distinction is critically important when casting a returned -1 error value to some other
 // unsigned type: (A)-1 != (B)-1 when A and B are unsigned types of different sizes).
 template <typename Unsigned>
 Unsigned as_unsigned(PyObject *o) {
-    if (sizeof(Unsigned) <= sizeof(unsigned long)
-#if PY_VERSION_HEX < 0x03000000
-            || PyInt_Check(o)
-#endif
-    ) {
-        unsigned long v = PyLong_AsUnsignedLong(o);
-        return v == (unsigned long) -1 && PyErr_Occurred() ? (Unsigned) -1 : (Unsigned) v;
+    using py_type = py_unsigned_int_type_for<Unsigned>;
+    py_type v = (sizeof(Unsigned) <= sizeof(unsigned long))
+        ? (py_type) PyLong_AsUnsignedLong(o)
+        : (py_type) PYBIND11_LONG_AS_UNSIGNED_LONGLONG(o);
+    return v == (py_unsigned_int_type_for<Unsigned>) -1 && PyErr_Occurred() ? (Unsigned) -1 : (Unsigned) v;
+}
+
+template <typename Int>
+Int as_integer(PyObject *o) {
+    if (std::is_unsigned<Int>::value) {
+        return as_unsigned<Int>(o);
     }
     else {
-        unsigned long long v = PyLong_AsUnsignedLongLong(o);
-        return v == (unsigned long long) -1 && PyErr_Occurred() ? (Unsigned) -1 : (Unsigned) v;
+        return sizeof(Int) <= sizeof(long)
+            ? (Int) PyLong_AsLong(o)
+            : (Int) PYBIND11_LONG_AS_LONGLONG(o);
     }
 }
 PYBIND11_NAMESPACE_END(detail)
@@ -1137,11 +1152,18 @@ class int_ : public object {
     template <typename T,
               detail::enable_if_t<std::is_integral<T>::value, int> = 0>
     operator T() const {
-        return std::is_unsigned<T>::value
-            ? detail::as_unsigned<T>(m_ptr)
-            : sizeof(T) <= sizeof(long)
-              ? (T) PyLong_AsLong(m_ptr)
-              : (T) PYBIND11_LONG_AS_LONGLONG(m_ptr);
+        using py_type = detail::py_int_type_for<T>;
+        auto value = detail::as_integer<py_type>(m_ptr);
+        if (PyErr_Occurred())
+            throw error_already_set();
+        if (sizeof(py_type) != sizeof(T) && value != (py_type) (T) value)
+#if defined(NDEBUG)
+            throw cast_error("Unable to cast Python instance to C++ type (compile in debug mode for details)");
+#else
+            throw cast_error("Unable to cast Python instance of type " +
+                (std::string) pybind11::str(type::handle_of(*this)) + " to C++ type '" + type_id<T>() + "'");
+#endif
+        return (T) value;
     }
 };
 
diff --git a/tests/test_pytypes.cpp b/tests/test_pytypes.cpp
index 709611d222..21453f5763 100644
--- a/tests/test_pytypes.cpp
+++ b/tests/test_pytypes.cpp
@@ -270,6 +270,7 @@ TEST_SUBMODULE(pytypes, m) {
         throw std::runtime_error("Invalid type");
     });
 
+    // test_implicit_casting
     m.def("get_implicit_casting", []() {
         py::dict d;
         d["char*_i1"] = "abc";
@@ -307,6 +308,12 @@ TEST_SUBMODULE(pytypes, m) {
         );
     });
 
+    // (see also test_builtin_casters)
+    m.def("implicitly_cast_to_int32", [](py::int_ value) { return int32_t{value}; });
+    m.def("implicitly_cast_to_uint32", [](py::int_ value) { return uint32_t{value}; });
+    m.def("implicitly_cast_to_int64", [](py::int_ value) { return int64_t{value}; });
+    m.def("implicitly_cast_to_uint64", [](py::int_ value) { return uint64_t{value}; });
+
     // test_print
     m.def("print_function", []() {
         py::print("Hello, World!");
diff --git a/tests/test_pytypes.py b/tests/test_pytypes.py
index b1509a0200..e6b57219d4 100644
--- a/tests/test_pytypes.py
+++ b/tests/test_pytypes.py
@@ -331,6 +331,26 @@ def test_implicit_casting():
     }
     assert z["l"] == [3, 6, 9, 12, 15]
 
+    assert m.implicitly_cast_to_int32(42) == 42
+    assert m.implicitly_cast_to_int32(2 ** 31 - 1) == 2 ** 31 - 1
+    with pytest.raises(RuntimeError, match="Unable to cast Python instance"):
+        m.implicitly_cast_to_int32(2 ** 31)
+
+    assert m.implicitly_cast_to_uint32(42) == 42
+    assert m.implicitly_cast_to_uint32(2 ** 32 - 1) == 2 ** 32 - 1
+    with pytest.raises(RuntimeError, match="Unable to cast Python instance"):
+        m.implicitly_cast_to_uint32(2 ** 32)
+
+    assert m.implicitly_cast_to_int64(42) == 42
+    assert m.implicitly_cast_to_int64(2 ** 63 - 1) == 2 ** 63 - 1
+    with pytest.raises(RuntimeError, match="Unable to cast Python instance"):
+        m.implicitly_cast_to_int64(2 ** 63)
+
+    assert m.implicitly_cast_to_uint64(42) == 42
+    assert m.implicitly_cast_to_uint64(2 ** 64 - 1) == 2 ** 64 - 1
+    with pytest.raises(RuntimeError, match="Unable to cast Python instance"):
+        m.implicitly_cast_to_uint64(2 ** 64)
+
 
 def test_print(capture):
     with capture: