diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 56f222cd94ab6f..d0204df035a720 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -270,7 +270,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-24.04]
-        openssl_ver: [3.0.16, 3.1.8, 3.2.4, 3.3.3, 3.4.1]
+        openssl_ver: [3.0.17, 3.2.5, 3.3.4, 3.4.2, 3.5.2]
         # See Tools/ssl/make_ssl_data.py for notes on adding a new version
     env:
       OPENSSL_VER: ${{ matrix.openssl_ver }}
diff --git a/Lib/test/test_coroutines.py b/Lib/test/test_coroutines.py
index 42b13064befaa9..6ad7e7994f32b0 100644
--- a/Lib/test/test_coroutines.py
+++ b/Lib/test/test_coroutines.py
@@ -1008,7 +1008,7 @@ async def foo():
             return (await Awaitable())
 
         with self.assertRaisesRegex(
-            TypeError, "__await__.*returned non-iterator of type"):
+            TypeError, "__await__.*must return an iterator, not"):
 
             run_async(foo())
 
@@ -1106,7 +1106,7 @@ async def foo():
             return await Awaitable()
 
         with self.assertRaisesRegex(
-                TypeError, r"__await__\(\) returned a coroutine"):
+                TypeError, r"__await__\(\) must return an iterator, not coroutine"):
             run_async(foo())
 
         c.close()
@@ -1120,7 +1120,7 @@ async def foo():
             return await Awaitable()
 
         with self.assertRaisesRegex(
-            TypeError, "__await__.*returned non-iterator of type"):
+            TypeError, "__await__.*must return an iterator, not"):
 
             run_async(foo())
 
@@ -2490,7 +2490,7 @@ async def foo():
             return (await future)
 
         with self.assertRaisesRegex(
-                TypeError, "__await__.*returned non-iterator of type 'int'"):
+                TypeError, "__await__.*must return an iterator, not int"):
             self.assertEqual(foo().send(None), 1)
 
 
diff --git a/Lib/test/test_type_annotations.py b/Lib/test/test_type_annotations.py
index c66cb058552643..1415bbca22707c 100644
--- a/Lib/test/test_type_annotations.py
+++ b/Lib/test/test_type_annotations.py
@@ -309,7 +309,7 @@ def check_annotations(self, f):
             print(f.__annotations__)
 
         f.__annotate__ = lambda x: 42
-        with self.assertRaisesRegex(TypeError, r"__annotate__ returned non-dict of type 'int'"):
+        with self.assertRaisesRegex(TypeError, r"__annotate__\(\) must return a dict, not int"):
             print(f.__annotations__)
 
         f.__annotate__ = lambda x: {"x": x}
diff --git a/Misc/NEWS.d/next/Build/2025-08-13-12-10-12.gh-issue-132339.3Czz5y.rst b/Misc/NEWS.d/next/Build/2025-08-13-12-10-12.gh-issue-132339.3Czz5y.rst
new file mode 100644
index 00000000000000..493be0ca2da966
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2025-08-13-12-10-12.gh-issue-132339.3Czz5y.rst
@@ -0,0 +1 @@
+Add support for OpenSSL 3.5.
diff --git a/Misc/NEWS.d/next/C_API/2025-08-13-13-41-04.gh-issue-137573.r6uwRf.rst b/Misc/NEWS.d/next/C_API/2025-08-13-13-41-04.gh-issue-137573.r6uwRf.rst
new file mode 100644
index 00000000000000..dcf0e643dc1ed3
--- /dev/null
+++ b/Misc/NEWS.d/next/C_API/2025-08-13-13-41-04.gh-issue-137573.r6uwRf.rst
@@ -0,0 +1,2 @@
+Mark ``_PyOptimizer_Optimize`` as :c:macro:`Py_NO_INLINE` to
+prevent stack overflow crashes on macOS.
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2025-04-28-18-59-11.gh-issue-130821.B11LU1.rst b/Misc/NEWS.d/next/Core_and_Builtins/2025-04-28-18-59-11.gh-issue-130821.B11LU1.rst
new file mode 100644
index 00000000000000..09ffaf80a6d535
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2025-04-28-18-59-11.gh-issue-130821.B11LU1.rst
@@ -0,0 +1,2 @@
+Enhance wrong type error messages and make them more consistent. Patch by
+Semyon Moroz.
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index a74654b7573f45..fde49fd0d2cd09 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -150,7 +150,7 @@ static void _PySSLFixErrno(void) {
 /* Include generated data (error codes) */
 /* See make_ssl_data.h for notes on adding a new version. */
 #if (OPENSSL_VERSION_NUMBER >= 0x30401000L)
-#include "_ssl_data_34.h"
+#include "_ssl_data_35.h"
 #elif (OPENSSL_VERSION_NUMBER >= 0x30100000L)
 #include "_ssl_data_340.h"
 #elif (OPENSSL_VERSION_NUMBER >= 0x30000000L)
diff --git a/Modules/_ssl_data_34.h b/Modules/_ssl_data_35.h
similarity index 98%
rename from Modules/_ssl_data_34.h
rename to Modules/_ssl_data_35.h
index 99718c5e605acf..9e69eaa910f003 100644
--- a/Modules/_ssl_data_34.h
+++ b/Modules/_ssl_data_35.h
@@ -1,6 +1,6 @@
 /* File generated by Tools/ssl/make_ssl_data.py */
-/* Generated on 2025-03-26T13:47:34.223146+00:00 */
-/* Generated from Git commit openssl-3.4.1-0-ga26d85337d */
+/* Generated on 2025-08-13T16:42:33.155822+00:00 */
+/* Generated from Git commit openssl-3.5.2-0-g0893a6235 */
 
 /* generated from args.lib2errnum */
 static struct py_ssl_library_code library_codes[] = {
@@ -1283,6 +1283,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"FAILED_BUILDING_OWN_CHAIN", 58, 164},
   #endif
+  #ifdef CMP_R_FAILED_EXTRACTING_CENTRAL_GEN_KEY
+    {"FAILED_EXTRACTING_CENTRAL_GEN_KEY", ERR_LIB_CMP, CMP_R_FAILED_EXTRACTING_CENTRAL_GEN_KEY},
+  #else
+    {"FAILED_EXTRACTING_CENTRAL_GEN_KEY", 58, 203},
+  #endif
   #ifdef CMP_R_FAILED_EXTRACTING_PUBKEY
     {"FAILED_EXTRACTING_PUBKEY", ERR_LIB_CMP, CMP_R_FAILED_EXTRACTING_PUBKEY},
   #else
@@ -1343,6 +1348,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"INVALID_ROOTCAKEYUPDATE", 58, 195},
   #endif
+  #ifdef CMP_R_MISSING_CENTRAL_GEN_KEY
+    {"MISSING_CENTRAL_GEN_KEY", ERR_LIB_CMP, CMP_R_MISSING_CENTRAL_GEN_KEY},
+  #else
+    {"MISSING_CENTRAL_GEN_KEY", 58, 204},
+  #endif
   #ifdef CMP_R_MISSING_CERTID
     {"MISSING_CERTID", ERR_LIB_CMP, CMP_R_MISSING_CERTID},
   #else
@@ -1513,6 +1523,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"UNCLEAN_CTX", 58, 191},
   #endif
+  #ifdef CMP_R_UNEXPECTED_CENTRAL_GEN_KEY
+    {"UNEXPECTED_CENTRAL_GEN_KEY", ERR_LIB_CMP, CMP_R_UNEXPECTED_CENTRAL_GEN_KEY},
+  #else
+    {"UNEXPECTED_CENTRAL_GEN_KEY", 58, 205},
+  #endif
   #ifdef CMP_R_UNEXPECTED_CERTPROFILE
     {"UNEXPECTED_CERTPROFILE", ERR_LIB_CMP, CMP_R_UNEXPECTED_CERTPROFILE},
   #else
@@ -2308,6 +2323,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"BAD_PBM_ITERATIONCOUNT", 56, 100},
   #endif
+  #ifdef CRMF_R_CMS_NOT_SUPPORTED
+    {"CMS_NOT_SUPPORTED", ERR_LIB_CRMF, CRMF_R_CMS_NOT_SUPPORTED},
+  #else
+    {"CMS_NOT_SUPPORTED", 56, 122},
+  #endif
   #ifdef CRMF_R_CRMFERROR
     {"CRMFERROR", ERR_LIB_CRMF, CRMF_R_CRMFERROR},
   #else
@@ -2323,16 +2343,41 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"ERROR_DECODING_CERTIFICATE", 56, 104},
   #endif
+  #ifdef CRMF_R_ERROR_DECODING_ENCRYPTEDKEY
+    {"ERROR_DECODING_ENCRYPTEDKEY", ERR_LIB_CRMF, CRMF_R_ERROR_DECODING_ENCRYPTEDKEY},
+  #else
+    {"ERROR_DECODING_ENCRYPTEDKEY", 56, 123},
+  #endif
   #ifdef CRMF_R_ERROR_DECRYPTING_CERTIFICATE
     {"ERROR_DECRYPTING_CERTIFICATE", ERR_LIB_CRMF, CRMF_R_ERROR_DECRYPTING_CERTIFICATE},
   #else
     {"ERROR_DECRYPTING_CERTIFICATE", 56, 105},
   #endif
+  #ifdef CRMF_R_ERROR_DECRYPTING_ENCRYPTEDKEY
+    {"ERROR_DECRYPTING_ENCRYPTEDKEY", ERR_LIB_CRMF, CRMF_R_ERROR_DECRYPTING_ENCRYPTEDKEY},
+  #else
+    {"ERROR_DECRYPTING_ENCRYPTEDKEY", 56, 124},
+  #endif
+  #ifdef CRMF_R_ERROR_DECRYPTING_ENCRYPTEDVALUE
+    {"ERROR_DECRYPTING_ENCRYPTEDVALUE", ERR_LIB_CRMF, CRMF_R_ERROR_DECRYPTING_ENCRYPTEDVALUE},
+  #else
+    {"ERROR_DECRYPTING_ENCRYPTEDVALUE", 56, 125},
+  #endif
   #ifdef CRMF_R_ERROR_DECRYPTING_SYMMETRIC_KEY
     {"ERROR_DECRYPTING_SYMMETRIC_KEY", ERR_LIB_CRMF, CRMF_R_ERROR_DECRYPTING_SYMMETRIC_KEY},
   #else
     {"ERROR_DECRYPTING_SYMMETRIC_KEY", 56, 106},
   #endif
+  #ifdef CRMF_R_ERROR_SETTING_PURPOSE
+    {"ERROR_SETTING_PURPOSE", ERR_LIB_CRMF, CRMF_R_ERROR_SETTING_PURPOSE},
+  #else
+    {"ERROR_SETTING_PURPOSE", 56, 126},
+  #endif
+  #ifdef CRMF_R_ERROR_VERIFYING_ENCRYPTEDKEY
+    {"ERROR_VERIFYING_ENCRYPTEDKEY", ERR_LIB_CRMF, CRMF_R_ERROR_VERIFYING_ENCRYPTEDKEY},
+  #else
+    {"ERROR_VERIFYING_ENCRYPTEDKEY", 56, 127},
+  #endif
   #ifdef CRMF_R_FAILURE_OBTAINING_RANDOM
     {"FAILURE_OBTAINING_RANDOM", ERR_LIB_CRMF, CRMF_R_FAILURE_OBTAINING_RANDOM},
   #else
@@ -2358,6 +2403,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"POPOSKINPUT_NOT_SUPPORTED", 56, 113},
   #endif
+  #ifdef CRMF_R_POPO_INCONSISTENT_CENTRAL_KEYGEN
+    {"POPO_INCONSISTENT_CENTRAL_KEYGEN", ERR_LIB_CRMF, CRMF_R_POPO_INCONSISTENT_CENTRAL_KEYGEN},
+  #else
+    {"POPO_INCONSISTENT_CENTRAL_KEYGEN", 56, 128},
+  #endif
   #ifdef CRMF_R_POPO_INCONSISTENT_PUBLIC_KEY
     {"POPO_INCONSISTENT_PUBLIC_KEY", ERR_LIB_CRMF, CRMF_R_POPO_INCONSISTENT_PUBLIC_KEY},
   #else
@@ -3963,6 +4013,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"PBKDF2_ERROR", 6, 181},
   #endif
+  #ifdef EVP_R_PIPELINE_NOT_SUPPORTED
+    {"PIPELINE_NOT_SUPPORTED", ERR_LIB_EVP, EVP_R_PIPELINE_NOT_SUPPORTED},
+  #else
+    {"PIPELINE_NOT_SUPPORTED", 6, 230},
+  #endif
   #ifdef EVP_R_PKEY_APPLICATION_ASN1_METHOD_ALREADY_REGISTERED
     {"PKEY_APPLICATION_ASN1_METHOD_ALREADY_REGISTERED", ERR_LIB_EVP, EVP_R_PKEY_APPLICATION_ASN1_METHOD_ALREADY_REGISTERED},
   #else
@@ -3978,6 +4033,36 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"PRIVATE_KEY_ENCODE_ERROR", 6, 146},
   #endif
+  #ifdef EVP_R_PROVIDER_ASYM_CIPHER_FAILURE
+    {"PROVIDER_ASYM_CIPHER_FAILURE", ERR_LIB_EVP, EVP_R_PROVIDER_ASYM_CIPHER_FAILURE},
+  #else
+    {"PROVIDER_ASYM_CIPHER_FAILURE", 6, 232},
+  #endif
+  #ifdef EVP_R_PROVIDER_ASYM_CIPHER_NOT_SUPPORTED
+    {"PROVIDER_ASYM_CIPHER_NOT_SUPPORTED", ERR_LIB_EVP, EVP_R_PROVIDER_ASYM_CIPHER_NOT_SUPPORTED},
+  #else
+    {"PROVIDER_ASYM_CIPHER_NOT_SUPPORTED", 6, 235},
+  #endif
+  #ifdef EVP_R_PROVIDER_KEYMGMT_FAILURE
+    {"PROVIDER_KEYMGMT_FAILURE", ERR_LIB_EVP, EVP_R_PROVIDER_KEYMGMT_FAILURE},
+  #else
+    {"PROVIDER_KEYMGMT_FAILURE", 6, 233},
+  #endif
+  #ifdef EVP_R_PROVIDER_KEYMGMT_NOT_SUPPORTED
+    {"PROVIDER_KEYMGMT_NOT_SUPPORTED", ERR_LIB_EVP, EVP_R_PROVIDER_KEYMGMT_NOT_SUPPORTED},
+  #else
+    {"PROVIDER_KEYMGMT_NOT_SUPPORTED", 6, 236},
+  #endif
+  #ifdef EVP_R_PROVIDER_SIGNATURE_FAILURE
+    {"PROVIDER_SIGNATURE_FAILURE", ERR_LIB_EVP, EVP_R_PROVIDER_SIGNATURE_FAILURE},
+  #else
+    {"PROVIDER_SIGNATURE_FAILURE", 6, 234},
+  #endif
+  #ifdef EVP_R_PROVIDER_SIGNATURE_NOT_SUPPORTED
+    {"PROVIDER_SIGNATURE_NOT_SUPPORTED", ERR_LIB_EVP, EVP_R_PROVIDER_SIGNATURE_NOT_SUPPORTED},
+  #else
+    {"PROVIDER_SIGNATURE_NOT_SUPPORTED", 6, 237},
+  #endif
   #ifdef EVP_R_PUBLIC_KEY_NOT_RSA
     {"PUBLIC_KEY_NOT_RSA", ERR_LIB_EVP, EVP_R_PUBLIC_KEY_NOT_RSA},
   #else
@@ -3998,6 +4083,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"SIGNATURE_TYPE_AND_KEY_TYPE_INCOMPATIBLE", 6, 228},
   #endif
+  #ifdef EVP_R_TOO_MANY_PIPES
+    {"TOO_MANY_PIPES", ERR_LIB_EVP, EVP_R_TOO_MANY_PIPES},
+  #else
+    {"TOO_MANY_PIPES", 6, 231},
+  #endif
   #ifdef EVP_R_TOO_MANY_RECORDS
     {"TOO_MANY_RECORDS", ERR_LIB_EVP, EVP_R_TOO_MANY_RECORDS},
   #else
@@ -4753,6 +4843,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"UNSUPPORTED_PUBLIC_KEY_TYPE", 9, 110},
   #endif
+  #ifdef PEM_R_UNSUPPORTED_PVK_KEY_TYPE
+    {"UNSUPPORTED_PVK_KEY_TYPE", ERR_LIB_PEM, PEM_R_UNSUPPORTED_PVK_KEY_TYPE},
+  #else
+    {"UNSUPPORTED_PVK_KEY_TYPE", 9, 133},
+  #endif
   #ifdef PKCS12_R_CALLBACK_FAILED
     {"CALLBACK_FAILED", ERR_LIB_PKCS12, PKCS12_R_CALLBACK_FAILED},
   #else
@@ -5543,6 +5638,16 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"MISSING_XCGHASH", 57, 135},
   #endif
+  #ifdef PROV_R_ML_DSA_NO_FORMAT
+    {"ML_DSA_NO_FORMAT", ERR_LIB_PROV, PROV_R_ML_DSA_NO_FORMAT},
+  #else
+    {"ML_DSA_NO_FORMAT", 57, 245},
+  #endif
+  #ifdef PROV_R_ML_KEM_NO_FORMAT
+    {"ML_KEM_NO_FORMAT", ERR_LIB_PROV, PROV_R_ML_KEM_NO_FORMAT},
+  #else
+    {"ML_KEM_NO_FORMAT", 57, 246},
+  #endif
   #ifdef PROV_R_MODULE_INTEGRITY_FAILURE
     {"MODULE_INTEGRITY_FAILURE", ERR_LIB_PROV, PROV_R_MODULE_INTEGRITY_FAILURE},
   #else
@@ -5593,6 +5698,16 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"NO_PARAMETERS_SET", 57, 177},
   #endif
+  #ifdef PROV_R_NULL_LENGTH_POINTER
+    {"NULL_LENGTH_POINTER", ERR_LIB_PROV, PROV_R_NULL_LENGTH_POINTER},
+  #else
+    {"NULL_LENGTH_POINTER", 57, 247},
+  #endif
+  #ifdef PROV_R_NULL_OUTPUT_BUFFER
+    {"NULL_OUTPUT_BUFFER", ERR_LIB_PROV, PROV_R_NULL_OUTPUT_BUFFER},
+  #else
+    {"NULL_OUTPUT_BUFFER", 57, 248},
+  #endif
   #ifdef PROV_R_ONESHOT_CALL_OUT_OF_ORDER
     {"ONESHOT_CALL_OUT_OF_ORDER", ERR_LIB_PROV, PROV_R_ONESHOT_CALL_OUT_OF_ORDER},
   #else
@@ -5728,6 +5843,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"UNABLE_TO_RESEED", 57, 204},
   #endif
+  #ifdef PROV_R_UNEXPECTED_KEY_PARAMETERS
+    {"UNEXPECTED_KEY_PARAMETERS", ERR_LIB_PROV, PROV_R_UNEXPECTED_KEY_PARAMETERS},
+  #else
+    {"UNEXPECTED_KEY_PARAMETERS", 57, 249},
+  #endif
   #ifdef PROV_R_UNSUPPORTED_CEK_ALG
     {"UNSUPPORTED_CEK_ALG", ERR_LIB_PROV, PROV_R_UNSUPPORTED_CEK_ALG},
   #else
@@ -5748,6 +5868,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"UNSUPPORTED_NUMBER_OF_ROUNDS", 57, 152},
   #endif
+  #ifdef PROV_R_UNSUPPORTED_SELECTION
+    {"UNSUPPORTED_SELECTION", ERR_LIB_PROV, PROV_R_UNSUPPORTED_SELECTION},
+  #else
+    {"UNSUPPORTED_SELECTION", 57, 250},
+  #endif
   #ifdef PROV_R_UPDATE_CALL_OUT_OF_ORDER
     {"UPDATE_CALL_OUT_OF_ORDER", ERR_LIB_PROV, PROV_R_UPDATE_CALL_OUT_OF_ORDER},
   #else
@@ -5763,6 +5888,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"VALUE_ERROR", 57, 138},
   #endif
+  #ifdef PROV_R_WRONG_CIPHERTEXT_SIZE
+    {"WRONG_CIPHERTEXT_SIZE", ERR_LIB_PROV, PROV_R_WRONG_CIPHERTEXT_SIZE},
+  #else
+    {"WRONG_CIPHERTEXT_SIZE", 57, 251},
+  #endif
   #ifdef PROV_R_WRONG_FINAL_BLOCK_LENGTH
     {"WRONG_FINAL_BLOCK_LENGTH", ERR_LIB_PROV, PROV_R_WRONG_FINAL_BLOCK_LENGTH},
   #else
@@ -5938,6 +6068,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"PRNG_NOT_SEEDED", 36, 100},
   #endif
+  #ifdef RAND_R_RANDOM_POOL_IS_EMPTY
+    {"RANDOM_POOL_IS_EMPTY", ERR_LIB_RAND, RAND_R_RANDOM_POOL_IS_EMPTY},
+  #else
+    {"RANDOM_POOL_IS_EMPTY", 36, 142},
+  #endif
   #ifdef RAND_R_RANDOM_POOL_OVERFLOW
     {"RANDOM_POOL_OVERFLOW", ERR_LIB_RAND, RAND_R_RANDOM_POOL_OVERFLOW},
   #else
@@ -6923,6 +7058,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"DIGEST_CHECK_FAILED", 20, 149},
   #endif
+  #ifdef SSL_R_DOMAIN_USE_ONLY
+    {"DOMAIN_USE_ONLY", ERR_LIB_SSL, SSL_R_DOMAIN_USE_ONLY},
+  #else
+    {"DOMAIN_USE_ONLY", 20, 422},
+  #endif
   #ifdef SSL_R_DTLS_MESSAGE_TOO_BIG
     {"DTLS_MESSAGE_TOO_BIG", ERR_LIB_SSL, SSL_R_DTLS_MESSAGE_TOO_BIG},
   #else
@@ -7213,6 +7353,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"LIBRARY_HAS_NO_CIPHERS", 20, 161},
   #endif
+  #ifdef SSL_R_LISTENER_USE_ONLY
+    {"LISTENER_USE_ONLY", ERR_LIB_SSL, SSL_R_LISTENER_USE_ONLY},
+  #else
+    {"LISTENER_USE_ONLY", 20, 421},
+  #endif
   #ifdef SSL_R_MAXIMUM_ENCRYPTED_PKTS_REACHED
     {"MAXIMUM_ENCRYPTED_PKTS_REACHED", ERR_LIB_SSL, SSL_R_MAXIMUM_ENCRYPTED_PKTS_REACHED},
   #else
@@ -7243,6 +7388,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"MISSING_PSK_KEX_MODES_EXTENSION", 20, 310},
   #endif
+  #ifdef SSL_R_MISSING_QUIC_TLS_FUNCTIONS
+    {"MISSING_QUIC_TLS_FUNCTIONS", ERR_LIB_SSL, SSL_R_MISSING_QUIC_TLS_FUNCTIONS},
+  #else
+    {"MISSING_QUIC_TLS_FUNCTIONS", 20, 423},
+  #endif
   #ifdef SSL_R_MISSING_RSA_CERTIFICATE
     {"MISSING_RSA_CERTIFICATE", ERR_LIB_SSL, SSL_R_MISSING_RSA_CERTIFICATE},
   #else
@@ -8983,6 +9133,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"POLICY_WHEN_PROXY_LANGUAGE_REQUIRES_NO_POLICY", 34, 159},
   #endif
+  #ifdef X509V3_R_PURPOSE_NOT_UNIQUE
+    {"PURPOSE_NOT_UNIQUE", ERR_LIB_X509V3, X509V3_R_PURPOSE_NOT_UNIQUE},
+  #else
+    {"PURPOSE_NOT_UNIQUE", 34, 173},
+  #endif
   #ifdef X509V3_R_SECTION_NOT_FOUND
     {"SECTION_NOT_FOUND", ERR_LIB_X509V3, X509V3_R_SECTION_NOT_FOUND},
   #else
diff --git a/Objects/abstract.c b/Objects/abstract.c
index df96b935eccb44..8adad8407d04d4 100644
--- a/Objects/abstract.c
+++ b/Objects/abstract.c
@@ -132,8 +132,9 @@ PyObject_LengthHint(PyObject *o, Py_ssize_t defaultvalue)
         return defaultvalue;
     }
     if (!PyLong_Check(result)) {
-        PyErr_Format(PyExc_TypeError, "__length_hint__ must be an integer, not %.100s",
-            Py_TYPE(result)->tp_name);
+        PyErr_Format(PyExc_TypeError,
+                     "%T.__length_hint__() must return an int, not %T",
+                     o, result);
         Py_DECREF(result);
         return -1;
     }
@@ -143,7 +144,8 @@ PyObject_LengthHint(PyObject *o, Py_ssize_t defaultvalue)
         return -1;
     }
     if (res < 0) {
-        PyErr_Format(PyExc_ValueError, "__length_hint__() should return >= 0");
+        PyErr_Format(PyExc_ValueError,
+                     "%T.__length_hint__() must return a non-negative int", o);
         return -1;
     }
     return res;
@@ -887,8 +889,8 @@ PyObject_Format(PyObject *obj, PyObject *format_spec)
 
     if (result && !PyUnicode_Check(result)) {
         PyErr_Format(PyExc_TypeError,
-                     "__format__ must return a str, not %.200s",
-                     Py_TYPE(result)->tp_name);
+                     "%T.__format__() must return a str, not %T",
+                     obj, result);
         Py_SETREF(result, NULL);
         goto done;
     }
@@ -1421,17 +1423,17 @@ _PyNumber_Index(PyObject *item)
 
     if (!PyLong_Check(result)) {
         PyErr_Format(PyExc_TypeError,
-                     "__index__ returned non-int (type %.200s)",
-                     Py_TYPE(result)->tp_name);
+                     "%T.__index__() must return an int, not %T",
+                     item, result);
         Py_DECREF(result);
         return NULL;
     }
     /* Issue #17576: warn if 'result' not of exact type int. */
     if (PyErr_WarnFormat(PyExc_DeprecationWarning, 1,
-            "__index__ returned non-int (type %.200s).  "
+            "%T.__index__() must return an int, not %T.  "
             "The ability to return an instance of a strict subclass of int "
             "is deprecated, and may be removed in a future version of Python.",
-            Py_TYPE(result)->tp_name)) {
+            item, result)) {
         Py_DECREF(result);
         return NULL;
     }
@@ -1531,17 +1533,17 @@ PyNumber_Long(PyObject *o)
 
         if (!PyLong_Check(result)) {
             PyErr_Format(PyExc_TypeError,
-                         "__int__ returned non-int (type %.200s)",
-                         Py_TYPE(result)->tp_name);
+                         "%T.__int__() must return an int, not %T",
+                         o, result);
             Py_DECREF(result);
             return NULL;
         }
         /* Issue #17576: warn if 'result' not of exact type int. */
         if (PyErr_WarnFormat(PyExc_DeprecationWarning, 1,
-                "__int__ returned non-int (type %.200s).  "
+                "%T.__int__() must return an int, not %T.  "
                 "The ability to return an instance of a strict subclass of int "
                 "is deprecated, and may be removed in a future version of Python.",
-                Py_TYPE(result)->tp_name)) {
+                o, result)) {
             Py_DECREF(result);
             return NULL;
         }
@@ -1609,17 +1611,16 @@ PyNumber_Float(PyObject *o)
 
         if (!PyFloat_Check(res)) {
             PyErr_Format(PyExc_TypeError,
-                         "%.50s.__float__ returned non-float (type %.50s)",
-                         Py_TYPE(o)->tp_name, Py_TYPE(res)->tp_name);
+                         "%T.__float__() must return a float, not %T", o, res);
             Py_DECREF(res);
             return NULL;
         }
         /* Issue #26983: warn if 'res' not of exact type float. */
         if (PyErr_WarnFormat(PyExc_DeprecationWarning, 1,
-                "%.50s.__float__ returned non-float (type %.50s).  "
+                "%T.__float__() must return a float, not %T.  "
                 "The ability to return an instance of a strict subclass of float "
                 "is deprecated, and may be removed in a future version of Python.",
-                Py_TYPE(o)->tp_name, Py_TYPE(res)->tp_name)) {
+                o, res)) {
             Py_DECREF(res);
             return NULL;
         }
@@ -2435,10 +2436,8 @@ method_output_as_list(PyObject *o, PyObject *meth)
         PyThreadState *tstate = _PyThreadState_GET();
         if (_PyErr_ExceptionMatches(tstate, PyExc_TypeError)) {
             _PyErr_Format(tstate, PyExc_TypeError,
-                          "%.200s.%U() returned a non-iterable (type %.200s)",
-                          Py_TYPE(o)->tp_name,
-                          meth,
-                          Py_TYPE(meth_output)->tp_name);
+                          "%T.%U() must return an iterable, not %T",
+                          o, meth, meth_output);
         }
         Py_DECREF(meth_output);
         return NULL;
@@ -2818,9 +2817,8 @@ PyObject_GetIter(PyObject *o)
         PyObject *res = (*f)(o);
         if (res != NULL && !PyIter_Check(res)) {
             PyErr_Format(PyExc_TypeError,
-                         "iter() returned non-iterator "
-                         "of type '%.100s'",
-                         Py_TYPE(res)->tp_name);
+                         "%T.__iter__() must return an iterator, not %T",
+                         o, res);
             Py_SETREF(res, NULL);
         }
         return res;
@@ -2839,8 +2837,8 @@ PyObject_GetAIter(PyObject *o) {
     PyObject *it = (*f)(o);
     if (it != NULL && !PyAIter_Check(it)) {
         PyErr_Format(PyExc_TypeError,
-                     "aiter() returned not an async iterator of type '%.100s'",
-                     Py_TYPE(it)->tp_name);
+                     "%T.__aiter__() must return an async iterator, not %T",
+                     o, it);
         Py_SETREF(it, NULL);
     }
     return it;
diff --git a/Objects/bytesobject.c b/Objects/bytesobject.c
index 87ea1162e03513..933a371f6bbcc0 100644
--- a/Objects/bytesobject.c
+++ b/Objects/bytesobject.c
@@ -566,8 +566,8 @@ format_obj(PyObject *v, const char **pbuf, Py_ssize_t *plen)
             return NULL;
         if (!PyBytes_Check(result)) {
             PyErr_Format(PyExc_TypeError,
-                         "__bytes__ returned non-bytes (type %.200s)",
-                         Py_TYPE(result)->tp_name);
+                         "%T.__bytes__() must return a bytes, not %T",
+                         v, result);
             Py_DECREF(result);
             return NULL;
         }
@@ -2793,8 +2793,8 @@ bytes_new_impl(PyTypeObject *type, PyObject *x, const char *encoding,
             return NULL;
         if (!PyBytes_Check(bytes)) {
             PyErr_Format(PyExc_TypeError,
-                        "__bytes__ returned non-bytes (type %.200s)",
-                        Py_TYPE(bytes)->tp_name);
+                         "%T.__bytes__() must return a bytes, not %T",
+                         x, bytes);
             Py_DECREF(bytes);
             return NULL;
         }
diff --git a/Objects/complexobject.c b/Objects/complexobject.c
index b66ebe131ae605..9a5e11289a30a7 100644
--- a/Objects/complexobject.c
+++ b/Objects/complexobject.c
@@ -515,17 +515,17 @@ try_complex_special_method(PyObject *op)
         }
         if (!PyComplex_Check(res)) {
             PyErr_Format(PyExc_TypeError,
-                "__complex__ returned non-complex (type %.200s)",
-                Py_TYPE(res)->tp_name);
+                "%T.__complex__() must return a complex, not %T",
+                op, res);
             Py_DECREF(res);
             return NULL;
         }
         /* Issue #29894: warn if 'res' not of exact type complex. */
         if (PyErr_WarnFormat(PyExc_DeprecationWarning, 1,
-                "__complex__ returned non-complex (type %.200s).  "
+                "%T.__complex__() must return a complex, not %T.  "
                 "The ability to return an instance of a strict subclass of complex "
                 "is deprecated, and may be removed in a future version of Python.",
-                Py_TYPE(res)->tp_name)) {
+                op, res)) {
             Py_DECREF(res);
             return NULL;
         }
diff --git a/Objects/fileobject.c b/Objects/fileobject.c
index e624405bd5f62f..05c3e75b4642ee 100644
--- a/Objects/fileobject.c
+++ b/Objects/fileobject.c
@@ -68,9 +68,9 @@ PyFile_GetLine(PyObject *f, int n)
     }
     if (result != NULL && !PyBytes_Check(result) &&
         !PyUnicode_Check(result)) {
+        PyErr_Format(PyExc_TypeError,
+                     "%T.readline() must return a str, not %T", f, result);
         Py_SETREF(result, NULL);
-        PyErr_SetString(PyExc_TypeError,
-                   "object.readline() returned non-string");
     }
 
     if (n < 0 && result != NULL && PyBytes_Check(result)) {
@@ -193,8 +193,8 @@ PyObject_AsFileDescriptor(PyObject *o)
             Py_DECREF(fno);
         }
         else {
-            PyErr_SetString(PyExc_TypeError,
-                            "fileno() returned a non-integer");
+            PyErr_Format(PyExc_TypeError,
+                         "%T.fileno() must return an int, not %T", o, fno);
             Py_DECREF(fno);
             return -1;
         }
diff --git a/Objects/floatobject.c b/Objects/floatobject.c
index 93e1973d6b32fc..4e54e0829d3def 100644
--- a/Objects/floatobject.c
+++ b/Objects/floatobject.c
@@ -288,16 +288,16 @@ PyFloat_AsDouble(PyObject *op)
     if (!PyFloat_CheckExact(res)) {
         if (!PyFloat_Check(res)) {
             PyErr_Format(PyExc_TypeError,
-                         "%.50s.__float__ returned non-float (type %.50s)",
-                         Py_TYPE(op)->tp_name, Py_TYPE(res)->tp_name);
+                         "%T.__float__() must return a float, not %T",
+                         op, res);
             Py_DECREF(res);
             return -1;
         }
         if (PyErr_WarnFormat(PyExc_DeprecationWarning, 1,
-                "%.50s.__float__ returned non-float (type %.50s).  "
+                "%T.__float__() must return a float, not %T.  "
                 "The ability to return an instance of a strict subclass of float "
                 "is deprecated, and may be removed in a future version of Python.",
-                Py_TYPE(op)->tp_name, Py_TYPE(res)->tp_name)) {
+                op, res)) {
             Py_DECREF(res);
             return -1;
         }
diff --git a/Objects/funcobject.c b/Objects/funcobject.c
index 9532c21fc7082e..d8a10075578087 100644
--- a/Objects/funcobject.c
+++ b/Objects/funcobject.c
@@ -560,8 +560,9 @@ func_get_annotation_dict(PyFunctionObject *op)
             return NULL;
         }
         if (!PyDict_Check(ann_dict)) {
-            PyErr_Format(PyExc_TypeError, "__annotate__ returned non-dict of type '%.100s'",
-                         Py_TYPE(ann_dict)->tp_name);
+            PyErr_Format(PyExc_TypeError,
+                         "__annotate__() must return a dict, not %T",
+                         ann_dict);
             Py_DECREF(ann_dict);
             return NULL;
         }
diff --git a/Objects/genobject.c b/Objects/genobject.c
index 3e7d6257006cfd..bcde9e1a7be07e 100644
--- a/Objects/genobject.c
+++ b/Objects/genobject.c
@@ -1092,14 +1092,14 @@ _PyCoro_GetAwaitableIter(PyObject *o)
             if (PyCoro_CheckExact(res) || gen_is_coroutine(res)) {
                 /* __await__ must return an *iterator*, not
                    a coroutine or another awaitable (see PEP 492) */
-                PyErr_SetString(PyExc_TypeError,
-                                "__await__() returned a coroutine");
+                PyErr_Format(PyExc_TypeError,
+                             "%T.__await__() must return an iterator, "
+                             "not coroutine", o);
                 Py_CLEAR(res);
             } else if (!PyIter_Check(res)) {
                 PyErr_Format(PyExc_TypeError,
-                             "__await__() returned non-iterator "
-                             "of type '%.100s'",
-                             Py_TYPE(res)->tp_name);
+                             "%T.__await__() must return an iterator, "
+                             "not %T", o, res);
                 Py_CLEAR(res);
             }
         }
diff --git a/Objects/iterobject.c b/Objects/iterobject.c
index 5712e02ae828ab..e323987601d5d4 100644
--- a/Objects/iterobject.c
+++ b/Objects/iterobject.c
@@ -357,8 +357,9 @@ anextawaitable_getiter(anextawaitableobject *obj)
         }
         Py_SETREF(awaitable, new_awaitable);
         if (!PyIter_Check(awaitable)) {
-            PyErr_SetString(PyExc_TypeError,
-                            "__await__ returned a non-iterable");
+            PyErr_Format(PyExc_TypeError,
+                         "%T.__await__() must return an iterable, not %T",
+                         obj, awaitable);
             Py_DECREF(awaitable);
             return NULL;
         }
diff --git a/Objects/moduleobject.c b/Objects/moduleobject.c
index 862395e7881870..47681e4251849c 100644
--- a/Objects/moduleobject.c
+++ b/Objects/moduleobject.c
@@ -1329,8 +1329,9 @@ module_get_annotations(PyObject *self, void *Py_UNUSED(ignored))
                 return NULL;
             }
             if (!PyDict_Check(annotations)) {
-                PyErr_Format(PyExc_TypeError, "__annotate__ returned non-dict of type '%.100s'",
-                             Py_TYPE(annotations)->tp_name);
+                PyErr_Format(PyExc_TypeError,
+                             "__annotate__() must return a dict, not %T",
+                             annotations);
                 Py_DECREF(annotate);
                 Py_DECREF(annotations);
                 Py_DECREF(dict);
diff --git a/Objects/object.c b/Objects/object.c
index 479f4176a46039..fba86e63cd4a11 100644
--- a/Objects/object.c
+++ b/Objects/object.c
@@ -784,8 +784,7 @@ PyObject_Repr(PyObject *v)
     }
     if (!PyUnicode_Check(res)) {
         _PyErr_Format(tstate, PyExc_TypeError,
-                      "__repr__ returned non-string (type %.200s)",
-                      Py_TYPE(res)->tp_name);
+                      "%T.__repr__() must return a str, not %T", v, res);
         Py_DECREF(res);
         return NULL;
     }
@@ -827,8 +826,7 @@ PyObject_Str(PyObject *v)
     }
     if (!PyUnicode_Check(res)) {
         _PyErr_Format(tstate, PyExc_TypeError,
-                      "__str__ returned non-string (type %.200s)",
-                      Py_TYPE(res)->tp_name);
+                      "%T.__str__() must return a str, not %T", v, res);
         Py_DECREF(res);
         return NULL;
     }
@@ -883,8 +881,8 @@ PyObject_Bytes(PyObject *v)
             return NULL;
         if (!PyBytes_Check(result)) {
             PyErr_Format(PyExc_TypeError,
-                         "__bytes__ returned non-bytes (type %.200s)",
-                         Py_TYPE(result)->tp_name);
+                         "%T.__bytes__() must return a bytes, not %T",
+                         v, result);
             Py_DECREF(result);
             return NULL;
         }
diff --git a/Objects/typeobject.c b/Objects/typeobject.c
index 14bc5a4bc49f84..fb33bc747d885b 100644
--- a/Objects/typeobject.c
+++ b/Objects/typeobject.c
@@ -2168,8 +2168,9 @@ type_get_annotations(PyObject *tp, void *Py_UNUSED(closure))
                 return NULL;
             }
             if (!PyDict_Check(annotations)) {
-                PyErr_Format(PyExc_TypeError, "__annotate__ returned non-dict of type '%.100s'",
-                             Py_TYPE(annotations)->tp_name);
+                PyErr_Format(PyExc_TypeError,
+                             "__annotate__() must return a dict, not %T",
+                             annotations);
                 Py_DECREF(annotations);
                 Py_DECREF(annotate);
                 Py_DECREF(dict);
@@ -3510,10 +3511,8 @@ mro_check(PyTypeObject *type, PyObject *mro)
     for (i = 0; i < n; i++) {
         PyObject *obj = PyTuple_GET_ITEM(mro, i);
         if (!PyType_Check(obj)) {
-            PyErr_Format(
-                PyExc_TypeError,
-                "mro() returned a non-class ('%.500s')",
-                Py_TYPE(obj)->tp_name);
+            PyErr_Format(PyExc_TypeError,
+                         "%N.mro() returned a non-class ('%T')", type, obj);
             return -1;
         }
         PyTypeObject *base = (PyTypeObject*)obj;
@@ -3521,8 +3520,8 @@ mro_check(PyTypeObject *type, PyObject *mro)
         if (!is_subtype_with_mro(lookup_tp_mro(solid), solid, solid_base(base))) {
             PyErr_Format(
                 PyExc_TypeError,
-                "mro() returned base with unsuitable layout ('%.500s')",
-                base->tp_name);
+                "%N.mro() returned base with unsuitable layout ('%N')",
+                type, base);
             return -1;
         }
     }
@@ -10419,9 +10418,8 @@ slot_nb_bool(PyObject *self)
     }
     else {
         PyErr_Format(PyExc_TypeError,
-                     "__bool__ should return "
-                     "bool, returned %s",
-                     Py_TYPE(value)->tp_name);
+                     "%T.__bool__() must return a bool, not %T",
+                     self, value);
         result = -1;
     }
     Py_DECREF(value);
@@ -10901,7 +10899,8 @@ slot_bf_getbuffer(PyObject *self, Py_buffer *buffer, int flags)
     }
     if (!PyMemoryView_Check(ret)) {
         PyErr_Format(PyExc_TypeError,
-                     "__buffer__ returned non-memoryview object");
+                     "%T.__buffer__() must return a memoryview, not %T",
+                     self, ret);
         goto fail;
     }
 
diff --git a/Python/optimizer.c b/Python/optimizer.c
index f06df9644a1614..1d899ee8971368 100644
--- a/Python/optimizer.c
+++ b/Python/optimizer.c
@@ -109,7 +109,8 @@ uop_optimize(_PyInterpreterFrame *frame, _Py_CODEUNIT *instr,
 /* Returns 1 if optimized, 0 if not optimized, and -1 for an error.
  * If optimized, *executor_ptr contains a new reference to the executor
  */
-int
+// gh-137573: inlining this function causes stack overflows
+Py_NO_INLINE int
 _PyOptimizer_Optimize(
     _PyInterpreterFrame *frame, _Py_CODEUNIT *start,
     _PyExecutorObject **executor_ptr, int chain_depth)
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index f4c8fde8346fd9..e632adafaaa0a0 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -44,14 +44,15 @@
 
 OPENSSL_OLD_VERSIONS = [
     "1.1.1w",
+    "3.1.8",
 ]
 
 OPENSSL_RECENT_VERSIONS = [
     "3.0.16",
-    "3.1.8",
-    "3.2.4",
-    "3.3.3",
-    "3.4.1",
+    "3.2.5",
+    "3.3.4",
+    "3.4.2",
+    "3.5.2",
     # See make_ssl_data.py for notes on adding a new version.
 ]
 
@@ -74,8 +75,7 @@
 parser = argparse.ArgumentParser(
     prog='multissl',
     description=(
-        "Run CPython tests with multiple cryptography libraries"
-        "versions."
+        "Run CPython tests with multiple cryptography libraries/versions."
     ),
 )
 parser.add_argument(