diff --git a/nucypher/config/base.py b/nucypher/config/base.py
index 4188e2db4..952af7b63 100644
--- a/nucypher/config/base.py
+++ b/nucypher/config/base.py
@@ -19,7 +19,6 @@
 import json
 import os
 import re
-import tempfile
 from abc import ABC, abstractmethod
 from decimal import Decimal
 from pathlib import Path
@@ -31,7 +30,6 @@ from constant_sorrow.constants import (
     UNINITIALIZED_CONFIGURATION,
     NO_KEYSTORE_ATTACHED,
     NO_BLOCKCHAIN_CONNECTION,
-    FEDERATED_ADDRESS,
     DEVELOPMENT_CONFIGURATION,
     LIVE_CONFIGURATION
 )
@@ -57,6 +55,7 @@ from nucypher.crypto.powers import CryptoPower, CryptoPowerUp
 from nucypher.crypto.umbral_adapter import Signature
 from nucypher.network.middleware import RestMiddleware
 from nucypher.utilities.logging import Logger
+from umbral.signing import Signature
 
 
 class BaseConfiguration(ABC):
@@ -758,7 +757,7 @@ class CharacterConfiguration(BaseConfiguration):
                 power_ups.append(power_up)
         return power_ups
 
-    def initialize(self, password: str) -> str:
+    def initialize(self, password: str, force: bool = False) -> str:
         """Initialize a new configuration and write installation files to disk."""
 
         # Development
@@ -769,7 +768,7 @@ class CharacterConfiguration(BaseConfiguration):
         # Persistent
         else:
             self._ensure_config_root_exists()
-            self.write_keystore(password=password)
+            self.write_keystore(password=password, force=force)
 
         self._cache_runtime_filepaths()
         self.node_storage.initialize()
@@ -783,8 +782,8 @@ class CharacterConfiguration(BaseConfiguration):
         self.log.debug(message)
         return self.config_root
 
-    def write_keystore(self, password: str) -> Keystore:
-        self.__keystore = Keystore.generate(password=password, keystore_dir=self.keystore_dir)
+    def write_keystore(self, password: str, force: bool = False) -> Keystore:
+        self.__keystore = Keystore.generate(password=password, keystore_dir=self.keystore_dir, force=force)
         return self.keystore
 
     @classmethod
diff --git a/nucypher/crypto/keystore.py b/nucypher/crypto/keystore.py
index 7687ea0bd..ce883f49d 100644
--- a/nucypher/crypto/keystore.py
+++ b/nucypher/crypto/keystore.py
@@ -20,13 +20,13 @@ import json
 import os
 import stat
 import string
-import tempfile
 from json import JSONDecodeError
 from os.path import abspath
 from pathlib import Path
 from secrets import token_bytes
 from typing import Callable, ClassVar, Dict, List, Union, Optional, Tuple
 
+import click
 import time
 from constant_sorrow.constants import KEYSTORE_LOCKED
 from cryptography.hazmat.backends import default_backend
@@ -36,6 +36,7 @@ from mnemonic.mnemonic import Mnemonic
 from nacl.exceptions import CryptoError
 from nacl.secret import SecretBox
 
+from nucypher.characters.control.emitters import StdoutEmitter
 from nucypher.config.constants import DEFAULT_CONFIG_ROOT
 from nucypher.crypto.constants import BLAKE2B
 from nucypher.crypto.keypairs import HostingKeypair
@@ -340,6 +341,7 @@ class Keystore:
 
     @classmethod
     def restore(cls, words: str, password: str, keystore_dir: Optional[Path] = None) -> 'Keystore':
+        """Restore a keystore from seed words"""
         __mnemonic = Mnemonic(_MNEMONIC_LANGUAGE)
         __secret = __mnemonic.to_entropy(words)
         path = Keystore.__save(secret=__secret, password=password, keystore_dir=keystore_dir)
@@ -347,14 +349,40 @@ class Keystore:
         return keystore
 
     @classmethod
-    def generate(cls, password: str, keystore_dir: Optional[Path] = None) -> 'Keystore':
+    def generate(cls, password: str, keystore_dir: Optional[Path] = None, force: bool = False) -> 'Keystore':
+        """Generate a new nucypher keystore for use with characters"""
         mnemonic = Mnemonic(_MNEMONIC_LANGUAGE)
         __words = mnemonic.generate(strength=_ENTROPY_BITS)
+        cls._confirm_generate(__words, force=force)
         __secret = mnemonic.to_entropy(__words)
         path = Keystore.__save(secret=__secret, password=password, keystore_dir=keystore_dir)
         keystore = cls(keystore_path=path)
         return keystore
 
+    @staticmethod
+    def _confirm_generate(__words: str, force: bool) -> None:
+        """
+        Inform the caller of new keystore seed words generation the console
+        and optionally perform interactive confirmation
+        """
+
+        # notification
+        emitter = StdoutEmitter()
+        emitter.message(f'Backup your seed words, you will not be able to view them again.\n')
+        emitter.message(f'{__words}\n', color='cyan')
+
+        # confirmation
+        if not force:
+            if not click.confirm("Have you backed up your seed phrase?"):
+                emitter.message('Keystore generation aborted.', color='red')
+                raise click.Abort()
+            click.clear()
+
+            __response = click.prompt("Confirm seed words")
+            if __response != __words:
+                raise ValueError('Incorrect seed word confirmation. No keystore has been created, try again.')
+        click.clear()
+
     @property
     def id(self) -> str:
         return self.__id
diff --git a/tests/fixtures.py b/tests/fixtures.py
index 0dc7664d1..737d0e58a 100644
--- a/tests/fixtures.py
+++ b/tests/fixtures.py
@@ -1051,3 +1051,9 @@ def stakeholder_configuration_file_location(custom_filepath):
 def mock_teacher_nodes(mocker):
     mock_nodes = tuple(u.rest_url() for u in MOCK_KNOWN_URSULAS_CACHE.values())[0:2]
     mocker.patch.dict(TEACHER_NODES, {TEMPORARY_DOMAIN: mock_nodes}, clear=True)
+
+
+@pytest.fixture(autouse=True)
+def disable_interactive_keystore_generation(mocker):
+    # Do not notify or confirm mnemonic seed words during tests normally
+    mocker.patch.object(Keystore, '_confirm_generate')