diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index d46ce5e60e2141..6117ca3fdba1b7 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -339,6 +339,15 @@ def test_constants(self):
         ssl.OP_NO_TLSv1_2
         self.assertEqual(ssl.PROTOCOL_TLS, ssl.PROTOCOL_SSLv23)
 
+    def test_options(self):
+        # gh-106687: SSL options values are unsigned integer (uint64_t)
+        for name in dir(ssl):
+            if not name.startswith('OP_'):
+                continue
+            with self.subTest(option=name):
+                value = getattr(ssl, name)
+                self.assertGreaterEqual(value, 0, f"ssl.{name}")
+
     def test_ssl_types(self):
         ssl_types = [
             _ssl._SSLContext,
@@ -951,6 +960,7 @@ def test_get_ciphers(self):
         )
 
     def test_options(self):
+        # Test default SSLContext options
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
         # OP_ALL | OP_NO_SSLv2 | OP_NO_SSLv3 is the default value
         default = (ssl.OP_ALL | ssl.OP_NO_SSLv2 | ssl.OP_NO_SSLv3)
@@ -959,16 +969,30 @@ def test_options(self):
                     OP_SINGLE_DH_USE | OP_SINGLE_ECDH_USE |
                     OP_ENABLE_MIDDLEBOX_COMPAT)
         self.assertEqual(default, ctx.options)
+
+        # disallow TLSv1
         with warnings_helper.check_warnings():
             ctx.options |= ssl.OP_NO_TLSv1
         self.assertEqual(default | ssl.OP_NO_TLSv1, ctx.options)
+
+        # allow TLSv1
         with warnings_helper.check_warnings():
             ctx.options = (ctx.options & ~ssl.OP_NO_TLSv1)
         self.assertEqual(default, ctx.options)
+
+        # clear all options
         ctx.options = 0
         # Ubuntu has OP_NO_SSLv3 forced on by default
         self.assertEqual(0, ctx.options & ~ssl.OP_NO_SSLv3)
 
+        # invalid options
+        with self.assertRaises(OverflowError):
+            ctx.options = -1
+        with self.assertRaises(OverflowError):
+            ctx.options = 2 ** 100
+        with self.assertRaises(TypeError):
+            ctx.options = "abc"
+
     def test_verify_mode_protocol(self):
         with warnings_helper.check_warnings():
             ctx = ssl.SSLContext(ssl.PROTOCOL_TLS)
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 571de331e92cd9..0cf4d3e9dc8c9b 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -3025,7 +3025,7 @@ _ssl__SSLContext_impl(PyTypeObject *type, int proto_version)
 /*[clinic end generated code: output=2cf0d7a0741b6bd1 input=8d58a805b95fc534]*/
 {
     PySSLContext *self;
-    long options;
+    uint64_t options;
     const SSL_METHOD *method = NULL;
     SSL_CTX *ctx = NULL;
     X509_VERIFY_PARAM *params;
@@ -3618,20 +3618,32 @@ PyDoc_STRVAR(PySSLContext_security_level_doc, "The current security level");
 static PyObject *
 get_options(PySSLContext *self, void *c)
 {
-    return PyLong_FromLong(SSL_CTX_get_options(self->ctx));
+    uint64_t options = SSL_CTX_get_options(self->ctx);
+    Py_BUILD_ASSERT(sizeof(unsigned long long) >= sizeof(options));
+    return PyLong_FromUnsignedLongLong(options);
 }
 
 static int
 set_options(PySSLContext *self, PyObject *arg, void *c)
 {
-    long new_opts, opts, set, clear;
-    long opt_no = (
+    PyObject *new_opts_obj;
+    unsigned long long new_opts_arg;
+    uint64_t new_opts, opts, clear, set;
+    uint64_t opt_no = (
         SSL_OP_NO_SSLv2 | SSL_OP_NO_SSLv3 | SSL_OP_NO_TLSv1 |
         SSL_OP_NO_TLSv1_1 | SSL_OP_NO_TLSv1_2 | SSL_OP_NO_TLSv1_3
     );
 
-    if (!PyArg_Parse(arg, "l", &new_opts))
+    if (!PyArg_Parse(arg, "O!", &PyLong_Type, &new_opts_obj)) {
         return -1;
+    }
+    new_opts_arg = PyLong_AsUnsignedLongLong(new_opts_obj);
+    if (new_opts_arg == (unsigned long long)-1 && PyErr_Occurred()) {
+        return -1;
+    }
+    Py_BUILD_ASSERT(sizeof(new_opts) >= sizeof(new_opts_arg));
+    new_opts = (uint64_t)new_opts_arg;
+
     opts = SSL_CTX_get_options(self->ctx);
     clear = opts & ~new_opts;
     set = ~opts & new_opts;
@@ -3645,8 +3657,9 @@ set_options(PySSLContext *self, PyObject *arg, void *c)
     if (clear) {
         SSL_CTX_clear_options(self->ctx, clear);
     }
-    if (set)
+    if (set) {
         SSL_CTX_set_options(self->ctx, set);
+    }
     return 0;
 }
 
@@ -5754,10 +5767,24 @@ sslmodule_init_socketapi(PyObject *module)
     return 0;
 }
 
+
 static int
-sslmodule_init_constants(PyObject *m)
+sslmodule_add_option(PyObject *m, const char *name, uint64_t value)
 {
+    Py_BUILD_ASSERT(sizeof(unsigned long long) >= sizeof(value));
+    PyObject *obj = PyLong_FromUnsignedLongLong(value);
+    if (obj == NULL) {
+        return -1;
+    }
+    int res = PyModule_AddObjectRef(m, name, obj);
+    Py_DECREF(obj);
+    return res;
+}
+
 
+static int
+sslmodule_init_constants(PyObject *m)
+{
     PyModule_AddStringConstant(m, "_DEFAULT_CIPHERS",
                                PY_SSL_DEFAULT_CIPHER_STRING);
 
@@ -5877,46 +5904,47 @@ sslmodule_init_constants(PyObject *m)
     PyModule_AddIntConstant(m, "PROTOCOL_TLSv1_2",
                             PY_SSL_VERSION_TLS1_2);
 
+#define ADD_OPTION(NAME, VALUE) if (sslmodule_add_option(m, NAME, (VALUE)) < 0) return -1
+
     /* protocol options */
-    PyModule_AddIntConstant(m, "OP_ALL",
-                            SSL_OP_ALL & ~SSL_OP_DONT_INSERT_EMPTY_FRAGMENTS);
-    PyModule_AddIntConstant(m, "OP_NO_SSLv2", SSL_OP_NO_SSLv2);
-    PyModule_AddIntConstant(m, "OP_NO_SSLv3", SSL_OP_NO_SSLv3);
-    PyModule_AddIntConstant(m, "OP_NO_TLSv1", SSL_OP_NO_TLSv1);
-    PyModule_AddIntConstant(m, "OP_NO_TLSv1_1", SSL_OP_NO_TLSv1_1);
-    PyModule_AddIntConstant(m, "OP_NO_TLSv1_2", SSL_OP_NO_TLSv1_2);
+    ADD_OPTION("OP_ALL", SSL_OP_ALL & ~SSL_OP_DONT_INSERT_EMPTY_FRAGMENTS);
+    ADD_OPTION("OP_NO_SSLv2", SSL_OP_NO_SSLv2);
+    ADD_OPTION("OP_NO_SSLv3", SSL_OP_NO_SSLv3);
+    ADD_OPTION("OP_NO_TLSv1", SSL_OP_NO_TLSv1);
+    ADD_OPTION("OP_NO_TLSv1_1", SSL_OP_NO_TLSv1_1);
+    ADD_OPTION("OP_NO_TLSv1_2", SSL_OP_NO_TLSv1_2);
 #ifdef SSL_OP_NO_TLSv1_3
-    PyModule_AddIntConstant(m, "OP_NO_TLSv1_3", SSL_OP_NO_TLSv1_3);
+    ADD_OPTION("OP_NO_TLSv1_3", SSL_OP_NO_TLSv1_3);
 #else
-    PyModule_AddIntConstant(m, "OP_NO_TLSv1_3", 0);
+    ADD_OPTION("OP_NO_TLSv1_3", 0);
 #endif
-    PyModule_AddIntConstant(m, "OP_CIPHER_SERVER_PREFERENCE",
+    ADD_OPTION("OP_CIPHER_SERVER_PREFERENCE",
                             SSL_OP_CIPHER_SERVER_PREFERENCE);
-    PyModule_AddIntConstant(m, "OP_SINGLE_DH_USE", SSL_OP_SINGLE_DH_USE);
-    PyModule_AddIntConstant(m, "OP_NO_TICKET", SSL_OP_NO_TICKET);
-    PyModule_AddIntConstant(m, "OP_LEGACY_SERVER_CONNECT",
+    ADD_OPTION("OP_SINGLE_DH_USE", SSL_OP_SINGLE_DH_USE);
+    ADD_OPTION("OP_NO_TICKET", SSL_OP_NO_TICKET);
+    ADD_OPTION("OP_LEGACY_SERVER_CONNECT",
                             SSL_OP_LEGACY_SERVER_CONNECT);
 #ifdef SSL_OP_SINGLE_ECDH_USE
-    PyModule_AddIntConstant(m, "OP_SINGLE_ECDH_USE", SSL_OP_SINGLE_ECDH_USE);
+    ADD_OPTION("OP_SINGLE_ECDH_USE", SSL_OP_SINGLE_ECDH_USE);
 #endif
 #ifdef SSL_OP_NO_COMPRESSION
-    PyModule_AddIntConstant(m, "OP_NO_COMPRESSION",
+    ADD_OPTION("OP_NO_COMPRESSION",
                             SSL_OP_NO_COMPRESSION);
 #endif
 #ifdef SSL_OP_ENABLE_MIDDLEBOX_COMPAT
-    PyModule_AddIntConstant(m, "OP_ENABLE_MIDDLEBOX_COMPAT",
+    ADD_OPTION("OP_ENABLE_MIDDLEBOX_COMPAT",
                             SSL_OP_ENABLE_MIDDLEBOX_COMPAT);
 #endif
 #ifdef SSL_OP_NO_RENEGOTIATION
-    PyModule_AddIntConstant(m, "OP_NO_RENEGOTIATION",
+    ADD_OPTION("OP_NO_RENEGOTIATION",
                             SSL_OP_NO_RENEGOTIATION);
 #endif
 #ifdef SSL_OP_IGNORE_UNEXPECTED_EOF
-    PyModule_AddIntConstant(m, "OP_IGNORE_UNEXPECTED_EOF",
+    ADD_OPTION("OP_IGNORE_UNEXPECTED_EOF",
                             SSL_OP_IGNORE_UNEXPECTED_EOF);
 #endif
 #ifdef SSL_OP_ENABLE_KTLS
-    PyModule_AddIntConstant(m, "OP_ENABLE_KTLS", SSL_OP_ENABLE_KTLS);
+    ADD_OPTION("OP_ENABLE_KTLS", SSL_OP_ENABLE_KTLS);
 #endif
 
 #ifdef X509_CHECK_FLAG_ALWAYS_CHECK_SUBJECT