diff --git a/cheroot/ssl/__init__.py b/cheroot/ssl/__init__.py
index 23c1e85675..458bdcc3d6 100644
--- a/cheroot/ssl/__init__.py
+++ b/cheroot/ssl/__init__.py
@@ -2,6 +2,7 @@
 
 import socket as _socket
 from abc import ABC, abstractmethod
+from getpass import getpass as _ask_for_password_interactively
 from warnings import warn as _warn
 
 from .. import errors as _errors
@@ -113,3 +114,8 @@ def get_environ(self):
     def makefile(self, sock, mode='r', bufsize=-1):
         """Return socket file object."""
         raise NotImplementedError  # pragma: no cover
+
+    def _prompt_for_tls_password(self) -> str:
+        """Prompt for encrypted private key password interactively."""
+        prompt = 'Enter PEM pass phrase: '
+        return _ask_for_password_interactively(prompt)
diff --git a/cheroot/ssl/__init__.pyi b/cheroot/ssl/__init__.pyi
index 31abe293f4..78e7d56e59 100644
--- a/cheroot/ssl/__init__.pyi
+++ b/cheroot/ssl/__init__.pyi
@@ -1,3 +1,4 @@
+import collections.abc as _c
 import typing as _t
 from abc import ABC, abstractmethod
 
@@ -6,8 +7,9 @@ class Adapter(ABC):
     private_key: _t.Any
     certificate_chain: _t.Any
     ciphers: _t.Any
-    private_key_password: str | bytes | None
+    private_key_password: _c.Callable[[], bytes | str] | bytes | str | None
     context: _t.Any
+
     @abstractmethod
     def __init__(
         self,
@@ -16,7 +18,10 @@ class Adapter(ABC):
         certificate_chain: _t.Any | None = ...,
         ciphers: _t.Any | None = ...,
         *,
-        private_key_password: str | bytes | None = ...,
+        private_key_password: _c.Callable[[], bytes | str]
+        | bytes
+        | str
+        | None = ...,
     ): ...
     def bind(self, sock): ...
     @abstractmethod
@@ -25,3 +30,4 @@ class Adapter(ABC):
     def get_environ(self): ...
     @abstractmethod
     def makefile(self, sock, mode: str = ..., bufsize: int = ...): ...
+    def _prompt_for_tls_password(self) -> str: ...
diff --git a/cheroot/ssl/builtin.py b/cheroot/ssl/builtin.py
index fcde32f93e..b7fed72b21 100644
--- a/cheroot/ssl/builtin.py
+++ b/cheroot/ssl/builtin.py
@@ -247,6 +247,9 @@ def __init__(
             private_key_password=private_key_password,
         )
 
+        if private_key_password is None:
+            private_key_password = self._prompt_for_tls_password
+
         self.context = ssl.create_default_context(
             purpose=ssl.Purpose.CLIENT_AUTH,
             cafile=certificate_chain,
diff --git a/cheroot/ssl/builtin.pyi b/cheroot/ssl/builtin.pyi
index 6b3f0eebf0..4032a326e6 100644
--- a/cheroot/ssl/builtin.pyi
+++ b/cheroot/ssl/builtin.pyi
@@ -1,3 +1,4 @@
+import collections.abc as _c
 import typing as _t
 
 from . import Adapter
@@ -14,7 +15,10 @@ class BuiltinSSLAdapter(Adapter):
         certificate_chain: _t.Any | None = ...,
         ciphers: _t.Any | None = ...,
         *,
-        private_key_password: str | bytes | None = ...,
+        private_key_password: _c.Callable[[], bytes | str]
+        | bytes
+        | str
+        | None = ...,
     ) -> None: ...
     @property
     def context(self): ...
diff --git a/cheroot/ssl/pyopenssl.py b/cheroot/ssl/pyopenssl.py
index 37fb136d74..6cf700341a 100644
--- a/cheroot/ssl/pyopenssl.py
+++ b/cheroot/ssl/pyopenssl.py
@@ -352,11 +352,20 @@ def wrap(self, sock):
     def _password_callback(
         self,
         password_max_length,
-        _verify_twice,
-        password,
+        verify_twice,
+        password_or_callback,
         /,
     ):
         """Pass a passphrase to password protected private key."""
+        if callable(password_or_callback):
+            password = password_or_callback()
+            if verify_twice and password != password_or_callback():
+                raise ValueError(
+                    'Verification failed: entered passwords do not match',
+                ) from None
+        else:
+            password = password_or_callback
+
         b_password = b''  # returning a falsy value communicates an error
         if isinstance(password, str):
             b_password = password.encode('utf-8')
@@ -381,6 +390,8 @@ def get_context(self):
         """
         # See https://code.activestate.com/recipes/442473/
         c = SSL.Context(SSL.SSLv23_METHOD)
+        if self.private_key_password is None:
+            self.private_key_password = self._prompt_for_tls_password
         c.set_passwd_cb(self._password_callback, self.private_key_password)
         c.use_privatekey_file(self.private_key)
         if self.certificate_chain:
diff --git a/cheroot/ssl/pyopenssl.pyi b/cheroot/ssl/pyopenssl.pyi
index 44c49e1530..6ca8d09eca 100644
--- a/cheroot/ssl/pyopenssl.pyi
+++ b/cheroot/ssl/pyopenssl.pyi
@@ -1,3 +1,4 @@
+import collections.abc as _c
 import typing as _t
 
 from OpenSSL import SSL
@@ -32,14 +33,20 @@ class pyOpenSSLAdapter(Adapter):
         certificate_chain: _t.Any | None = ...,
         ciphers: _t.Any | None = ...,
         *,
-        private_key_password: str | bytes | None = ...,
+        private_key_password: _c.Callable[[], bytes | str]
+        | bytes
+        | str
+        | None = ...,
     ) -> None: ...
     def wrap(self, sock): ...
     def _password_callback(
         self,
         password_max_length: int,
-        _verify_twice: bool,
-        password: bytes | str | None,
+        verify_twice: bool,
+        password_or_callback: _c.Callable[[], bytes | str]
+        | bytes
+        | str
+        | None,
         /,
     ) -> bytes: ...
     def get_environ(self): ...
diff --git a/cheroot/test/test_ssl.py b/cheroot/test/test_ssl.py
index 77fb0b96c4..1859e6bc28 100644
--- a/cheroot/test/test_ssl.py
+++ b/cheroot/test/test_ssl.py
@@ -149,10 +149,18 @@ def make_tls_http_server(bind_addr, ssl_adapter, request):
     return httpserver
 
 
+def get_key_password():
+    """Return a predefined password string.
+
+    It is to be used for decrypting private keys.
+    """
+    return 'криївка'
+
+
 @pytest.fixture(scope='session')
 def private_key_password():
     """Provide hardcoded password for private key."""
-    return 'криївка'
+    return get_key_password()
 
 
 @pytest.fixture
@@ -900,9 +908,17 @@ def test_http_over_https_ssl_handshake(
     ids=('encrypted-key', 'unencrypted-key'),
 )
 @pytest.mark.parametrize(
-    'password_as_bytes',
-    (True, False),
-    ids=('with-bytes-password', 'with-str-password'),
+    'transform_password_arg',
+    (
+        lambda pass_factory: pass_factory().encode('utf-8'),
+        lambda pass_factory: pass_factory(),
+        lambda pass_factory: pass_factory,
+    ),
+    ids=(
+        'with-bytes-password',
+        'with-str-password',
+        'with-callable-password-provider',
+    ),
 )
 # pylint: disable-next=too-many-positional-arguments
 def test_ssl_adapters_with_private_key_password(
@@ -915,7 +931,7 @@ def test_ssl_adapters_with_private_key_password(
     tls_certificate_private_key_pem_path,
     adapter_type,
     encrypted_key,
-    password_as_bytes,
+    transform_password_arg,
 ):
     """Check server decrypts private TLS keys with password as bytes or str."""
     key_file = (
@@ -923,17 +939,13 @@ def test_ssl_adapters_with_private_key_password(
         if encrypted_key
         else tls_certificate_private_key_pem_path
     )
-    key_pass = (
-        private_key_password.encode('utf-8')
-        if password_as_bytes
-        else private_key_password
-    )
+    private_key_password = transform_password_arg(get_key_password)
 
     tls_adapter_cls = get_ssl_adapter_class(name=adapter_type)
     tls_adapter = tls_adapter_cls(
         certificate=tls_certificate_chain_pem_path,
         private_key=key_file,
-        private_key_password=key_pass,
+        private_key_password=private_key_password,
     )
 
     interface, _host, port = _get_conn_data(
@@ -1015,6 +1027,76 @@ def test_openssl_adapter_with_false_key_password(
         )
 
 
+@pytest.mark.parametrize(
+    'adapter_type',
+    ('pyopenssl', 'builtin'),
+)
+def test_ssl_adapter_with_none_key_password(
+    tls_certificate_chain_pem_path,
+    tls_certificate_passwd_private_key_pem_path,
+    private_key_password,
+    adapter_type,
+    mocker,
+):
+    """Check that TLS-adapters prompt for password when set as ``None``."""
+    tls_adapter_cls = get_ssl_adapter_class(name=adapter_type)
+    mocker.patch(
+        'cheroot.ssl._ask_for_password_interactively',
+        return_value=private_key_password,
+    )
+    tls_adapter = tls_adapter_cls(
+        certificate=tls_certificate_chain_pem_path,
+        private_key=tls_certificate_passwd_private_key_pem_path,
+    )
+
+    assert tls_adapter.context is not None
+
+
+class PasswordCallbackHelper:
+    """Collects helper methods for mocking password callback."""
+
+    def __init__(self, adapter: Adapter):
+        """Initialize helper variables."""
+        self.counter = 0
+        self.callback = adapter._password_callback
+
+    def get_password(self):
+        """Provide correct password on first call, wrong on other calls."""
+        self.counter += 1
+        return get_key_password() * self.counter
+
+    def verify_twice_callback(self, max_length, _verify_twice, userdata):
+        """Establish a mock callback for testing two-factor password prompt."""
+        return self.callback(self, max_length, True, userdata)
+
+
+@pytest.mark.parametrize('adapter_type', ('pyopenssl',))
+def test_openssl_adapter_verify_twice_callback(
+    tls_certificate_chain_pem_path,
+    tls_certificate_passwd_private_key_pem_path,
+    adapter_type,
+    mocker,
+):
+    """Check that two-time password verification fails with correct error."""
+    tls_adapter_cls = get_ssl_adapter_class(name=adapter_type)
+    helper = PasswordCallbackHelper(tls_adapter_cls)
+
+    mocker.patch(
+        'cheroot.ssl.pyopenssl.pyOpenSSLAdapter._password_callback',
+        side_effect=helper.verify_twice_callback,
+    )
+
+    with pytest.raises(
+        ValueError,
+        match='Verification failed: entered passwords do not match',
+    ):
+        tls_adapter_cls(
+            certificate=tls_certificate_chain_pem_path,
+            private_key=tls_certificate_passwd_private_key_pem_path,
+            private_key_password=helper.get_password,
+        )
+
+
 @pytest.fixture
 def dummy_adapter(monkeypatch):
     """Provide a dummy SSL adapter instance."""
diff --git a/docs/changelog-fragments.d/798.bugfix.rst b/docs/changelog-fragments.d/798.bugfix.rst
new file mode 100644
index 0000000000..582588e9b9
--- /dev/null
+++ b/docs/changelog-fragments.d/798.bugfix.rst
@@ -0,0 +1,7 @@
+Fixed prompting for the encrypted private key password interactively,
+when the password in not set in the :py:attr:`private_key_password attribute
+<cheroot.ssl.pyopenssl.pyOpenSSLAdapter.private_key_password>` in the
+:py:class:`pyOpenSSL TLS adapter <cheroot.ssl.pyopenssl.pyOpenSSLAdapter>`.
+Also improved the private key password to accept the :py:class:`~collections.abc.Callable` type.
+
+-- by :user:`jatalahd`