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diff -up pyOpenSSL-0.13.1/OpenSSL/crypto/crypto.c.exception pyOpenSSL-0.13.1/OpenSSL/crypto/crypto.c
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--- pyOpenSSL-0.13.1/OpenSSL/crypto/crypto.c.exception	2018-05-04 18:56:35.946486574 +0200
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+++ pyOpenSSL-0.13.1/OpenSSL/crypto/crypto.c	2018-05-04 18:56:35.950486667 +0200
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@@ -45,26 +45,72 @@ global_passphrase_callback(char *buf, in
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     func = (PyObject *)cb_arg;
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     argv = Py_BuildValue("(i)", rwflag);
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-    if (argv == NULL)
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+    if (argv == NULL) {
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         return 0;
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+    }
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     ret = PyEval_CallObject(func, argv);
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     Py_DECREF(argv);
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-    if (ret == NULL)
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+    if (ret == NULL) {
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         return 0;
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-    if (!PyBytes_Check(ret))
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-    {
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+    }
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+    if (!PyBytes_Check(ret)) {
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         Py_DECREF(ret);
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         PyErr_SetString(PyExc_ValueError, "String expected");
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         return 0;
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     }
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     nchars = PyBytes_Size(ret);
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-    if (nchars > len)
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-        nchars = len;
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+    if (nchars > len) {
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+       Py_DECREF(ret);
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+       PyErr_SetString(PyExc_ValueError,
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+                        "passphrase returned by callback is too long");
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+       return 0;
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+    }
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     strncpy(buf, PyBytes_AsString(ret), nchars);
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     Py_DECREF(ret);
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     return nchars;
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 }
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+static PyObject *
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+raise_current_error(void)
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+{
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+    if (PyErr_Occurred()) {
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+        /*
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+         * The python exception from callback is more informative than
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+         * OpenSSL's error.
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+         */
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+        flush_error_queue();
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+        return NULL;
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+    }
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+    exception_from_error_queue(crypto_Error);
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+    return NULL;
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+}
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+
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+static int
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+setup_callback(int type, PyObject *pw, pem_password_cb **cb, void **cb_arg) {
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+    if (pw == NULL) {
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+        *cb = NULL;
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+        *cb_arg = NULL;
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+        return 1;
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+    }
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+    if (type != X509_FILETYPE_PEM) {
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+        PyErr_SetString(PyExc_ValueError,
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+                        "only FILETYPE_PEM key format supports encryption");
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+        return 0;
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+    }
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+    if (PyBytes_Check(pw)) {
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+        *cb = NULL;
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+        *cb_arg = PyBytes_AsString(pw);
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+    } else if (PyCallable_Check(pw)) {
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+        *cb = global_passphrase_callback;
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+        *cb_arg = pw;
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+    } else {
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+        PyErr_SetString(PyExc_TypeError,
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+                        "Last argument must be string or callable");
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+        return 0;
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+    }
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+    return 1;
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+}
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+
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 static char crypto_load_privatekey_doc[] = "\n\
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 Load a private key from a buffer\n\
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 \n\
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@@ -89,31 +135,20 @@ crypto_load_privatekey(PyObject *spam, P
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     BIO *bio;
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     EVP_PKEY *pkey;
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-    if (!PyArg_ParseTuple(args, "is#|O:load_privatekey", &type, &buffer, &len, &pw))
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+    if (!PyArg_ParseTuple(args, "is#|O:load_privatekey",
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+                          &type, &buffer, &len, &pw)) {
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+        return NULL;
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+    }
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+    if (!setup_callback(type, pw, &cb, &cb_arg)) {
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         return NULL;
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-
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-    if (pw != NULL)
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-    {
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-        if (PyBytes_Check(pw))
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-        {
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-            cb = NULL;
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-            cb_arg = PyBytes_AsString(pw);
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-        }
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-        else if (PyCallable_Check(pw))
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-        {
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-            cb = global_passphrase_callback;
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-            cb_arg = pw;
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-        }
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-        else
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-        {
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-            PyErr_SetString(PyExc_TypeError, "Last argument must be string or callable");
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-            return NULL;
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-        }
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     }
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     bio = BIO_new_mem_buf(buffer, len);
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-    switch (type)
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-    {
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+    if (bio == NULL) {
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+        exception_from_error_queue(crypto_Error);
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+        return NULL;
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+    }
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+    switch (type) {
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         case X509_FILETYPE_PEM:
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             pkey = PEM_read_bio_PrivateKey(bio, NULL, cb, cb_arg);
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             break;
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@@ -129,10 +164,8 @@ crypto_load_privatekey(PyObject *spam, P
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     }
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     BIO_free(bio);
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-    if (pkey == NULL)
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-    {
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-        exception_from_error_queue(crypto_Error);
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-        return NULL;
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+    if (pkey == NULL) {
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+        return raise_current_error();
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     }
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     return (PyObject *)crypto_PKey_New(pkey, 1);
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@@ -168,49 +201,32 @@ crypto_dump_privatekey(PyObject *spam, P
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     crypto_PKeyObj *pkey;
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     if (!PyArg_ParseTuple(args, "iO!|sO:dump_privatekey", &type,
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-			  &crypto_PKey_Type, &pkey, &cipher_name, &pw))
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+                          &crypto_PKey_Type, &pkey, &cipher_name, &pw)) {
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         return NULL;
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-
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-    if (cipher_name != NULL && pw == NULL)
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-    {
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+    }
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+    if (cipher_name != NULL && pw == NULL) {
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         PyErr_SetString(PyExc_ValueError, "Illegal number of arguments");
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         return NULL;
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     }
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-    if (cipher_name != NULL)
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-    {
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+    if (cipher_name != NULL) {
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         cipher = EVP_get_cipherbyname(cipher_name);
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-        if (cipher == NULL)
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-        {
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+        if (cipher == NULL) {
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             PyErr_SetString(PyExc_ValueError, "Invalid cipher name");
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             return NULL;
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         }
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-        if (PyBytes_Check(pw))
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-        {
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-            cb = NULL;
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-            cb_arg = PyBytes_AsString(pw);
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-        }
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-        else if (PyCallable_Check(pw))
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-        {
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-            cb = global_passphrase_callback;
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-            cb_arg = pw;
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-        }
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-        else
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-        {
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-            PyErr_SetString(PyExc_TypeError, "Last argument must be string or callable");
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+        if (!setup_callback(type, pw, &cb, &cb_arg)) {
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             return NULL;
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         }
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     }
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     bio = BIO_new(BIO_s_mem());
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-    switch (type)
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-    {
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+    if (bio == NULL) {
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+        exception_from_error_queue(crypto_Error);
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+        return NULL;
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+    }
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+    switch (type) {
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         case X509_FILETYPE_PEM:
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             ret = PEM_write_bio_PrivateKey(bio, pkey->pkey, cipher, NULL, 0, cb, cb_arg);
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-            if (PyErr_Occurred())
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-            {
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-                BIO_free(bio);
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-                return NULL;
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-            }
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             break;
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         case X509_FILETYPE_ASN1:
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@@ -219,8 +235,12 @@ crypto_dump_privatekey(PyObject *spam, P
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         case X509_FILETYPE_TEXT:
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             rsa = EVP_PKEY_get1_RSA(pkey->pkey);
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+            if (rsa == NULL) {
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+                ret = 0;
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+                break;
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+            }
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             ret = RSA_print(bio, rsa, 0);
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-            RSA_free(rsa); 
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+            RSA_free(rsa);
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             break;
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         default:
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@@ -229,11 +249,9 @@ crypto_dump_privatekey(PyObject *spam, P
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             return NULL;
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     }
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-    if (ret == 0)
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-    {
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+    if (ret == 0) {
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         BIO_free(bio);
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-        exception_from_error_queue(crypto_Error);
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-        return NULL;
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+        return raise_current_error();
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     }
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     buf_len = BIO_get_mem_data(bio, &temp);
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@@ -513,8 +531,8 @@ crypto_load_pkcs7_data(PyObject *spam, P
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     if (!PyArg_ParseTuple(args, "is#:load_pkcs7_data", &type, &buffer, &len))
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         return NULL;
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-    /* 
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-     * Try to read the pkcs7 data from the bio 
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+    /*
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+     * Try to read the pkcs7 data from the bio
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      */
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     bio = BIO_new_mem_buf(buffer, len);
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     switch (type)
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diff -up pyOpenSSL-0.13.1/OpenSSL/test/test_crypto.py.exception pyOpenSSL-0.13.1/OpenSSL/test/test_crypto.py
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--- pyOpenSSL-0.13.1/OpenSSL/test/test_crypto.py.exception	2018-05-04 18:56:35.948486620 +0200
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+++ pyOpenSSL-0.13.1/OpenSSL/test/test_crypto.py	2018-05-04 18:57:16.363420609 +0200
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@@ -7,7 +7,7 @@ Unit tests for L{OpenSSL.crypto}.
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 from unittest import main
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-import os, re
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+import os, re, sys
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 from subprocess import PIPE, Popen
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 from datetime import datetime, timedelta
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@@ -2038,6 +2038,18 @@ class FunctionTests(TestCase):
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             load_privatekey, FILETYPE_PEM, encryptedPrivateKeyPEM, b("quack"))
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+    def test_load_privatekey_passphraseWrongType(self):
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+        """
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+        :py:obj:`load_privatekey` raises :py:obj:`ValueError` when it is passed a passphrase
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+        with a private key encoded in a format, that doesn't support
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+        encryption.
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+        """
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+        key = load_privatekey(FILETYPE_PEM, cleartextPrivateKeyPEM)
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+        blob = dump_privatekey(FILETYPE_ASN1, key)
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+        self.assertRaises(ValueError,
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+            load_privatekey, FILETYPE_ASN1, blob, "secret")
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+
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+
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     def test_load_privatekey_passphrase(self):
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         """
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         L{load_privatekey} can create a L{PKey} object from an encrypted PEM
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@@ -2058,7 +2070,7 @@ class FunctionTests(TestCase):
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         called = []
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         def cb(*a):
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             called.append(None)
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-            return "quack"
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+            return b("quack")
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         self.assertRaises(
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             Error,
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             load_privatekey, FILETYPE_PEM, encryptedPrivateKeyPEM, cb)
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@@ -2083,25 +2095,36 @@ class FunctionTests(TestCase):
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     def test_load_privatekey_passphrase_exception(self):
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         """
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         An exception raised by the passphrase callback passed to
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-        L{load_privatekey} causes L{OpenSSL.crypto.Error} to be raised.
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-
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-        This isn't as nice as just letting the exception pass through.  The
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-        behavior might be changed to that eventually.
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+        L{load_privatekey} is propagated.
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         """
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         def broken(ignored):
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             raise RuntimeError("This is not working.")
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         self.assertRaises(
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-            Error,
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+            RuntimeError,
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             load_privatekey,
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             FILETYPE_PEM, encryptedPrivateKeyPEM, broken)
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+    def test_load_privatekey_passphrase_wrong_return_type(self):
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+        """
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+        :py:obj:`load_privatekey` raises :py:obj:`ValueError` if the passphrase
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+        callback returns something other than a byte string.
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+        """
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+        self.assertRaises(
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+            ValueError,
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+            load_privatekey,
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+            FILETYPE_PEM, encryptedPrivateKeyPEM, lambda *args: 3)
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+
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+
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     def test_dump_privatekey_wrong_args(self):
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         """
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         L{dump_privatekey} raises L{TypeError} if called with the wrong number
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         of arguments.
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         """
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         self.assertRaises(TypeError, dump_privatekey)
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+        # If cipher name is given, password is required.
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+        self.assertRaises(
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+            ValueError, dump_privatekey, FILETYPE_PEM, PKey(), "foo")
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     def test_dump_privatekey_unknown_cipher(self):
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@@ -2138,6 +2161,18 @@ class FunctionTests(TestCase):
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         self.assertRaises(ValueError, dump_privatekey, 100, key)
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+    def test_load_privatekey_passphraseCallbackLength(self):
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+        """
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+        :py:obj:`crypto.load_privatekey` should raise an error when the passphrase
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+        provided by the callback is too long, not silently truncate it.
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+        """
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+        def cb(ignored):
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+            return "a" * 1025
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+
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+        self.assertRaises(ValueError,
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+            load_privatekey, FILETYPE_PEM, encryptedPrivateKeyPEM, cb)
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+
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+
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     def test_dump_privatekey_passphrase(self):
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         """
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         L{dump_privatekey} writes an encrypted PEM when given a passphrase.
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@@ -2152,6 +2187,17 @@ class FunctionTests(TestCase):
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         self.assertEqual(loadedKey.bits(), key.bits())
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+    def test_dump_privatekey_passphraseWrongType(self):
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+        """
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+        :py:obj:`dump_privatekey` raises :py:obj:`ValueError` when it is passed a passphrase
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+        with a private key encoded in a format, that doesn't support
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+        encryption.
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+        """
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+        key = load_privatekey(FILETYPE_PEM, cleartextPrivateKeyPEM)
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+        self.assertRaises(ValueError,
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+            dump_privatekey, FILETYPE_ASN1, key, "blowfish", "secret")
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+
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+
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     def test_dump_certificate(self):
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         """
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         L{dump_certificate} writes PEM, DER, and text.
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@@ -2230,6 +2276,32 @@ class FunctionTests(TestCase):
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         self.assertEqual(loadedKey.bits(), key.bits())
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+    def test_dump_privatekey_passphrase_exception(self):
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+        """
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+        :py:obj:`dump_privatekey` should not overwrite the exception raised
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+        by the passphrase callback.
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+        """
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+        def cb(ignored):
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+            raise ArithmeticError
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+
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+        key = load_privatekey(FILETYPE_PEM, cleartextPrivateKeyPEM)
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+        self.assertRaises(ArithmeticError,
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+            dump_privatekey, FILETYPE_PEM, key, "blowfish", cb)
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+
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+
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+    def test_dump_privatekey_passphraseCallbackLength(self):
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+        """
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+        :py:obj:`crypto.dump_privatekey` should raise an error when the passphrase
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+        provided by the callback is too long, not silently truncate it.
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+        """
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+        def cb(ignored):
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+            return "a" * 1025
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+
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+        key = load_privatekey(FILETYPE_PEM, cleartextPrivateKeyPEM)
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+        self.assertRaises(ValueError,
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+            dump_privatekey, FILETYPE_PEM, key, "blowfish", cb)
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+
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+
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     def test_load_pkcs7_data(self):
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         """
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         L{load_pkcs7_data} accepts a PKCS#7 string and returns an instance of