Add private key password option to ssl adapters

- It is now possible to use password protected private keys
  in both builtin and openssl ssl-adapters

- Added also positive and negative unit test cases

- With reference to #1583

Author: jatalahd

cheroot/ssl/__init__.py

@@ -20,12 +20,15 @@ def __init__(
         private_key,
         certificate_chain=None,
         ciphers=None,
+        *,
+        private_key_password=None,
     ):
-        """Set up certificates, private key ciphers and reset context."""
+        """Set up certificates, private key, ciphers and reset context."""
         self.certificate = certificate
         self.private_key = private_key
         self.certificate_chain = certificate_chain
         self.ciphers = ciphers
+        self.private_key_password = private_key_password
         self.context = None
 
     @abstractmethod

cheroot/ssl/__init__.pyi

@@ -6,6 +6,7 @@ class Adapter(ABC):
     private_key: Any
     certificate_chain: Any
     ciphers: Any
+    private_key_password: str | bytes | None
     context: Any
     @abstractmethod
     def __init__(
@@ -14,6 +15,8 @@ class Adapter(ABC):
         private_key,
         certificate_chain: Any | None = ...,
         ciphers: Any | None = ...,
+        *,
+        private_key_password: str | bytes | None = ...,
     ): ...
     @abstractmethod
     def bind(self, sock): ...

cheroot/ssl/builtin.py

@@ -76,10 +76,20 @@ def _loopback_for_cert_thread(context, server):
             ssl_sock.send(b'0000')
 
 
-def _loopback_for_cert(certificate, private_key, certificate_chain):
+def _loopback_for_cert(
+    certificate,
+    private_key,
+    certificate_chain,
+    *,
+    private_key_password=None,
+):
     """Create a loopback connection to parse a cert with a private key."""
     context = ssl.create_default_context(cafile=certificate_chain)
-    context.load_cert_chain(certificate, private_key)
+    context.load_cert_chain(
+        certificate,
+        private_key,
+        password=private_key_password,
+    )
     context.check_hostname = False
     context.verify_mode = ssl.CERT_NONE
 
@@ -112,15 +122,26 @@ def _loopback_for_cert(certificate, private_key, certificate_chain):
         server.close()
 
 
-def _parse_cert(certificate, private_key, certificate_chain):
+def _parse_cert(
+    certificate,
+    private_key,
+    certificate_chain,
+    *,
+    private_key_password=None,
+):
     """Parse a certificate."""
     # loopback_for_cert uses socket.socketpair which was only
     # introduced in Python 3.0 for *nix and 3.5 for Windows
     # and requires OS support (AttributeError, OSError)
     # it also requires a private key either in its own file
     # or combined with the cert (SSLError)
     with suppress(AttributeError, ssl.SSLError, OSError):
-        return _loopback_for_cert(certificate, private_key, certificate_chain)
+        return _loopback_for_cert(
+            certificate,
+            private_key,
+            certificate_chain,
+            private_key_password=private_key_password,
+        )
 
     # KLUDGE: using an undocumented, private, test method to parse a cert
     # unfortunately, it is the only built-in way without a connection
@@ -153,6 +174,9 @@ class BuiltinSSLAdapter(Adapter):
     ciphers = None
     """The ciphers list of SSL."""
 
+    private_key_password = None
+    """Optional passphrase for password protected private key."""
+
     # from mod_ssl/pkg.sslmod/ssl_engine_vars.c ssl_var_lookup_ssl_cert
     CERT_KEY_TO_ENV = {
         'version': 'M_VERSION',
@@ -208,6 +232,8 @@ def __init__(
         private_key,
         certificate_chain=None,
         ciphers=None,
+        *,
+        private_key_password=None,
     ):
         """Set up context in addition to base class properties if available."""
         if ssl is None:
@@ -218,19 +244,29 @@ def __init__(
             private_key,
             certificate_chain,
             ciphers,
+            private_key_password=private_key_password,
         )
 
         self.context = ssl.create_default_context(
             purpose=ssl.Purpose.CLIENT_AUTH,
             cafile=certificate_chain,
         )
-        self.context.load_cert_chain(certificate, private_key)
+        self.context.load_cert_chain(
+            certificate,
+            private_key,
+            password=private_key_password,
+        )
         if self.ciphers is not None:
             self.context.set_ciphers(ciphers)
 
         self._server_env = self._make_env_cert_dict(
             'SSL_SERVER',
-            _parse_cert(certificate, private_key, self.certificate_chain),
+            _parse_cert(
+                certificate,
+                private_key,
+                self.certificate_chain,
+                private_key_password=private_key_password,
+            ),
         )
         if not self._server_env:
             return

cheroot/ssl/builtin.pyi

@@ -13,6 +13,8 @@ class BuiltinSSLAdapter(Adapter):
         private_key,
         certificate_chain: Any | None = ...,
         ciphers: Any | None = ...,
+        *,
+        private_key_password: str | bytes | None = ...,
     ) -> None: ...
     @property
     def context(self): ...

cheroot/ssl/pyopenssl.py

@@ -54,6 +54,7 @@
 import sys
 import threading
 import time
+from warnings import warn as _warn
 
 
 try:
@@ -293,12 +294,17 @@ class pyOpenSSLAdapter(Adapter):
     ciphers = None
     """The ciphers list of TLS."""
 
+    private_key_password = None
+    """Optional passphrase for password protected private key."""
+
     def __init__(
         self,
         certificate,
         private_key,
         certificate_chain=None,
         ciphers=None,
+        *,
+        private_key_password=None,
     ):
         """Initialize OpenSSL Adapter instance."""
         if SSL is None:
@@ -309,6 +315,7 @@ def __init__(
             private_key,
             certificate_chain,
             ciphers,
+            private_key_password=private_key_password,
         )
 
         self._environ = None
@@ -328,13 +335,39 @@ def wrap(self, sock):
         # closing so we can't reliably access protocol/client cert for the env
         return sock, self._environ.copy()
 
+    def _password_callback(
+        self,
+        password_max_length,
+        _verify_twice,
+        password,
+        /,
+    ):
+        """Pass a passphrase to password protected private key."""
+        b_password = b''  # returning a falsy value communicates an error
+        if isinstance(password, str):
+            b_password = password.encode('utf-8')
+        elif isinstance(password, bytes):
+            b_password = password
+
+        password_length = len(b_password)
+        if password_length > password_max_length:
+            _warn(
+                f'User-provided password is {password_length} bytes long and will '
+                f'be truncated since it exceeds the maximum of {password_max_length}.',
+                UserWarning,
+                stacklevel=1,
+            )
+
+        return b_password
+
     def get_context(self):
         """Return an ``SSL.Context`` from self attributes.
 
         Ref: :py:class:`SSL.Context <pyopenssl:OpenSSL.SSL.Context>`
         """
         # See https://code.activestate.com/recipes/442473/
         c = SSL.Context(SSL.SSLv23_METHOD)
+        c.set_passwd_cb(self._password_callback, self.private_key_password)
         c.use_privatekey_file(self.private_key)
         if self.certificate_chain:
             c.load_verify_locations(self.certificate_chain)

cheroot/ssl/pyopenssl.pyi

@@ -31,9 +31,18 @@ class pyOpenSSLAdapter(Adapter):
         private_key,
         certificate_chain: Any | None = ...,
         ciphers: Any | None = ...,
+        *,
+        private_key_password: str | bytes | None = ...,
     ) -> None: ...
     def bind(self, sock): ...
     def wrap(self, sock): ...
+    def _password_callback(
+        self,
+        password_max_length: int,
+        _verify_twice: bool,
+        password: bytes | str | None,
+        /,
+    ) -> bytes: ...
     def get_environ(self): ...
     def makefile(self, sock, mode: str = ..., bufsize: int = ...): ...
     def get_context(self) -> SSL.Context: ...