diff --git a/CHANGELOG.md b/CHANGELOG.md
index 69408a7fc..0aec3d277 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -49,6 +49,7 @@ Changelog](https://keepachangelog.com/en/1.0.0/).
 - Generate a random password when creating a new user for CommunicateAsNewUser
   PBA. #1434
 - Credentials gathered from victim machines are no longer stored plaintext in the database. #1454
+- Encrypt the database key with user's credentials. #1463
 
 
 ## [1.11.0] - 2021-08-13
diff --git a/monkey/monkey_island/cc/app.py b/monkey/monkey_island/cc/app.py
index 0bc20852f..5f877d318 100644
--- a/monkey/monkey_island/cc/app.py
+++ b/monkey/monkey_island/cc/app.py
@@ -54,7 +54,6 @@ from monkey_island.cc.resources.zero_trust.scoutsuite_auth.scoutsuite_auth impor
 from monkey_island.cc.resources.zero_trust.zero_trust_report import ZeroTrustReport
 from monkey_island.cc.server_utils.consts import MONKEY_ISLAND_ABS_PATH
 from monkey_island.cc.server_utils.custom_json_encoder import CustomJSONEncoder
-from monkey_island.cc.services.database import Database
 from monkey_island.cc.services.remote_run_aws import RemoteRunAwsService
 from monkey_island.cc.services.representations import output_json
 
@@ -108,7 +107,6 @@ def init_app_services(app):
 
     with app.app_context():
         database.init()
-        Database.init_db()
 
     # If running on AWS, this will initialize the instance data, which is used "later" in the
     # execution of the island.
diff --git a/monkey/monkey_island/cc/resources/auth/auth.py b/monkey/monkey_island/cc/resources/auth/auth.py
index 064395eaf..92a372a99 100644
--- a/monkey/monkey_island/cc/resources/auth/auth.py
+++ b/monkey/monkey_island/cc/resources/auth/auth.py
@@ -1,4 +1,3 @@
-import json
 import logging
 from functools import wraps
 
@@ -9,8 +8,12 @@ from flask_jwt_extended.exceptions import JWTExtendedException
 from jwt import PyJWTError
 
 import monkey_island.cc.environment.environment_singleton as env_singleton
-import monkey_island.cc.resources.auth.password_utils as password_utils
 import monkey_island.cc.resources.auth.user_store as user_store
+from monkey_island.cc.resources.auth.credential_utils import (
+    get_username_password_from_request,
+    password_matches_hash,
+)
+from monkey_island.cc.services.authentication import AuthenticationService
 
 logger = logging.getLogger(__name__)
 
@@ -38,28 +41,20 @@ class Authenticate(flask_restful.Resource):
             "password": "my_password"
         }
         """
-        (username, password) = _get_credentials_from_request(request)
+        username, password = get_username_password_from_request(request)
 
         if _credentials_match_registered_user(username, password):
+            AuthenticationService.ensure_datastore_encryptor(username, password)
             access_token = _create_access_token(username)
             return make_response({"access_token": access_token, "error": ""}, 200)
         else:
             return make_response({"error": "Invalid credentials"}, 401)
 
 
-def _get_credentials_from_request(request):
-    credentials = json.loads(request.data)
-
-    username = credentials["username"]
-    password = credentials["password"]
-
-    return (username, password)
-
-
-def _credentials_match_registered_user(username, password):
+def _credentials_match_registered_user(username: str, password: str) -> bool:
     user = user_store.UserStore.username_table.get(username, None)
 
-    if user and password_utils.password_matches_hash(password, user.secret):
+    if user and password_matches_hash(password, user.secret):
         return True
 
     return False
diff --git a/monkey/monkey_island/cc/resources/auth/credential_utils.py b/monkey/monkey_island/cc/resources/auth/credential_utils.py
new file mode 100644
index 000000000..a0823d42b
--- /dev/null
+++ b/monkey/monkey_island/cc/resources/auth/credential_utils.py
@@ -0,0 +1,32 @@
+import json
+from typing import Tuple
+
+import bcrypt
+from flask import Request, request
+
+from monkey_island.cc.environment.user_creds import UserCreds
+
+
+def hash_password(plaintext_password):
+    salt = bcrypt.gensalt()
+    password_hash = bcrypt.hashpw(plaintext_password.encode("utf-8"), salt)
+
+    return password_hash.decode()
+
+
+def password_matches_hash(plaintext_password, password_hash):
+    return bcrypt.checkpw(plaintext_password.encode("utf-8"), password_hash.encode("utf-8"))
+
+
+def get_user_credentials_from_request(_request) -> UserCreds:
+    username, password = get_username_password_from_request(_request)
+    password_hash = hash_password(password)
+
+    return UserCreds(username, password_hash)
+
+
+def get_username_password_from_request(_request: Request) -> Tuple[str, str]:
+    cred_dict = json.loads(request.data)
+    username = cred_dict.get("username", "")
+    password = cred_dict.get("password", "")
+    return username, password
diff --git a/monkey/monkey_island/cc/resources/auth/password_utils.py b/monkey/monkey_island/cc/resources/auth/password_utils.py
deleted file mode 100644
index f470fd882..000000000
--- a/monkey/monkey_island/cc/resources/auth/password_utils.py
+++ /dev/null
@@ -1,12 +0,0 @@
-import bcrypt
-
-
-def hash_password(plaintext_password):
-    salt = bcrypt.gensalt()
-    password_hash = bcrypt.hashpw(plaintext_password.encode("utf-8"), salt)
-
-    return password_hash.decode()
-
-
-def password_matches_hash(plaintext_password, password_hash):
-    return bcrypt.checkpw(plaintext_password.encode("utf-8"), password_hash.encode("utf-8"))
diff --git a/monkey/monkey_island/cc/resources/auth/registration.py b/monkey/monkey_island/cc/resources/auth/registration.py
index 12c17d6e5..670fa4d19 100644
--- a/monkey/monkey_island/cc/resources/auth/registration.py
+++ b/monkey/monkey_island/cc/resources/auth/registration.py
@@ -1,13 +1,15 @@
-import json
 import logging
 
 import flask_restful
 from flask import make_response, request
 
 import monkey_island.cc.environment.environment_singleton as env_singleton
-import monkey_island.cc.resources.auth.password_utils as password_utils
 from common.utils.exceptions import InvalidRegistrationCredentialsError, RegistrationNotNeededError
-from monkey_island.cc.environment.user_creds import UserCreds
+from monkey_island.cc.resources.auth.credential_utils import (
+    get_user_credentials_from_request,
+    get_username_password_from_request,
+)
+from monkey_island.cc.services.authentication import AuthenticationService
 from monkey_island.cc.setup.mongo.database_initializer import reset_database
 
 logger = logging.getLogger(__name__)
@@ -19,21 +21,13 @@ class Registration(flask_restful.Resource):
         return {"needs_registration": is_registration_needed}
 
     def post(self):
-        credentials = _get_user_credentials_from_request(request)
+        credentials = get_user_credentials_from_request(request)
 
         try:
             env_singleton.env.try_add_user(credentials)
+            username, password = get_username_password_from_request(request)
+            AuthenticationService.reset_datastore_encryptor(username, password)
             reset_database()
             return make_response({"error": ""}, 200)
         except (InvalidRegistrationCredentialsError, RegistrationNotNeededError) as e:
             return make_response({"error": str(e)}, 400)
-
-
-def _get_user_credentials_from_request(request):
-    cred_dict = json.loads(request.data)
-
-    username = cred_dict.get("user", "")
-    password = cred_dict.get("password", "")
-    password_hash = password_utils.hash_password(password)
-
-    return UserCreds(username, password_hash)
diff --git a/monkey/monkey_island/cc/resources/configuration_export.py b/monkey/monkey_island/cc/resources/configuration_export.py
index c550acc7d..111cfa177 100644
--- a/monkey/monkey_island/cc/resources/configuration_export.py
+++ b/monkey/monkey_island/cc/resources/configuration_export.py
@@ -4,7 +4,7 @@ import flask_restful
 from flask import request
 
 from monkey_island.cc.resources.auth.auth import jwt_required
-from monkey_island.cc.server_utils.encryption import PasswordBasedEncryptor
+from monkey_island.cc.server_utils.encryption import PasswordBasedStringEncryptor
 from monkey_island.cc.services.config import ConfigService
 
 
@@ -21,7 +21,7 @@ class ConfigurationExport(flask_restful.Resource):
             password = data["password"]
             plaintext_config = json.dumps(plaintext_config)
 
-            pb_encryptor = PasswordBasedEncryptor(password)
+            pb_encryptor = PasswordBasedStringEncryptor(password)
             config_export = pb_encryptor.encrypt(plaintext_config)
 
         return {"config_export": config_export, "encrypted": should_encrypt}
diff --git a/monkey/monkey_island/cc/resources/configuration_import.py b/monkey/monkey_island/cc/resources/configuration_import.py
index 6c0575e94..3a66a2ed0 100644
--- a/monkey/monkey_island/cc/resources/configuration_import.py
+++ b/monkey/monkey_island/cc/resources/configuration_import.py
@@ -11,7 +11,7 @@ from monkey_island.cc.resources.auth.auth import jwt_required
 from monkey_island.cc.server_utils.encryption import (
     InvalidCiphertextError,
     InvalidCredentialsError,
-    PasswordBasedEncryptor,
+    PasswordBasedStringEncryptor,
     is_encrypted,
 )
 from monkey_island.cc.services.config import ConfigService
@@ -72,7 +72,7 @@ class ConfigurationImport(flask_restful.Resource):
         try:
             config = request_contents["config"]
             if ConfigurationImport.is_config_encrypted(request_contents["config"]):
-                pb_encryptor = PasswordBasedEncryptor(request_contents["password"])
+                pb_encryptor = PasswordBasedStringEncryptor(request_contents["password"])
                 config = pb_encryptor.decrypt(config)
             return json.loads(config)
         except (JSONDecodeError, InvalidCiphertextError):
diff --git a/monkey/monkey_island/cc/server_setup.py b/monkey/monkey_island/cc/server_setup.py
index 69ab0437a..fdb94b67f 100644
--- a/monkey/monkey_island/cc/server_setup.py
+++ b/monkey/monkey_island/cc/server_setup.py
@@ -27,7 +27,6 @@ from monkey_island.cc.server_utils.consts import (  # noqa: E402
     GEVENT_EXCEPTION_LOG,
     MONGO_CONNECTION_TIMEOUT,
 )
-from monkey_island.cc.server_utils.encryption import initialize_datastore_encryptor  # noqa: E402
 from monkey_island.cc.server_utils.island_logger import reset_logger, setup_logging  # noqa: E402
 from monkey_island.cc.services.initialize import initialize_services  # noqa: E402
 from monkey_island.cc.services.reporting.exporter_init import populate_exporter_list  # noqa: E402
@@ -87,7 +86,6 @@ def _configure_logging(config_options):
 def _initialize_globals(config_options: IslandConfigOptions, server_config_path: str):
     env_singleton.initialize_from_file(server_config_path)
 
-    initialize_datastore_encryptor(config_options.data_dir)
     initialize_services(config_options.data_dir)
 
 
diff --git a/monkey/monkey_island/cc/server_utils/encryption/__init__.py b/monkey/monkey_island/cc/server_utils/encryption/__init__.py
index 7d806139c..109423634 100644
--- a/monkey/monkey_island/cc/server_utils/encryption/__init__.py
+++ b/monkey/monkey_island/cc/server_utils/encryption/__init__.py
@@ -1,15 +1,20 @@
-from monkey_island.cc.server_utils.encryption.i_encryptor import IEncryptor
-from monkey_island.cc.server_utils.encryption.key_based_encryptor import KeyBasedEncryptor
-from monkey_island.cc.server_utils.encryption.password_based_encryption import (
-    InvalidCiphertextError,
-    InvalidCredentialsError,
-    PasswordBasedEncryptor,
+from monkey_island.cc.server_utils.encryption.encryptors.i_encryptor import IEncryptor
+from monkey_island.cc.server_utils.encryption.encryptors.key_based_encryptor import (
+    KeyBasedEncryptor,
+)
+from monkey_island.cc.server_utils.encryption.encryptors.password_based_string_encryptior import (
+    PasswordBasedStringEncryptor,
     is_encrypted,
 )
-from monkey_island.cc.server_utils.encryption.data_store_encryptor import (
-    DataStoreEncryptor,
-    get_datastore_encryptor,
+from monkey_island.cc.server_utils.encryption.encryptors.password_based_bytes_encryption import (
+    PasswordBasedBytesEncryptor,
+    InvalidCredentialsError,
+    InvalidCiphertextError,
+)
+from .data_store_encryptor import (
     initialize_datastore_encryptor,
+    get_datastore_encryptor,
+    remove_old_datastore_key,
 )
 from .dict_encryption.dict_encryptor import (
     SensitiveField,
diff --git a/monkey/monkey_island/cc/server_utils/encryption/data_store_encryptor.py b/monkey/monkey_island/cc/server_utils/encryption/data_store_encryptor.py
index 215703c02..f7add80f3 100644
--- a/monkey/monkey_island/cc/server_utils/encryption/data_store_encryptor.py
+++ b/monkey/monkey_island/cc/server_utils/encryption/data_store_encryptor.py
@@ -1,50 +1,59 @@
 import os
+from typing import Union
 
-# PyCrypto is deprecated, but we use pycryptodome, which uses the exact same imports but
-# is maintained.
 from Crypto import Random  # noqa: DUO133  # nosec: B413
 
-from monkey_island.cc.server_utils.encryption import KeyBasedEncryptor
+from monkey_island.cc.server_utils.encryption import (
+    IEncryptor,
+    KeyBasedEncryptor,
+    PasswordBasedBytesEncryptor,
+)
 from monkey_island.cc.server_utils.file_utils import open_new_securely_permissioned_file
 
-_encryptor = None
+_KEY_FILENAME = "mongo_key.bin"
+_BLOCK_SIZE = 32
+
+_encryptor: Union[None, IEncryptor] = None
 
 
-class DataStoreEncryptor:
-    _BLOCK_SIZE = 32
-    _KEY_FILENAME = "mongo_key.bin"
-
-    def __init__(self, key_file_dir):
-        key_file = os.path.join(key_file_dir, self._KEY_FILENAME)
-
-        if os.path.exists(key_file):
-            self._load_existing_key(key_file)
-        else:
-            self._init_key(key_file)
-
-        self._key_base_encryptor = KeyBasedEncryptor(self._cipher_key)
-
-    def _init_key(self, password_file_path: str):
-        self._cipher_key = Random.new().read(self._BLOCK_SIZE)
-        with open_new_securely_permissioned_file(password_file_path, "wb") as f:
-            f.write(self._cipher_key)
-
-    def _load_existing_key(self, key_file):
-        with open(key_file, "rb") as f:
-            self._cipher_key = f.read()
-
-    def enc(self, message: str):
-        return self._key_base_encryptor.encrypt(message)
-
-    def dec(self, enc_message: str):
-        return self._key_base_encryptor.decrypt(enc_message)
+def _load_existing_key(key_file_path: str, secret: str) -> KeyBasedEncryptor:
+    with open(key_file_path, "rb") as f:
+        encrypted_key = f.read()
+    cipher_key = PasswordBasedBytesEncryptor(secret).decrypt(encrypted_key)
+    return KeyBasedEncryptor(cipher_key)
 
 
-def initialize_datastore_encryptor(key_file_dir):
+def _create_new_key(key_file_path: str, secret: str) -> KeyBasedEncryptor:
+    cipher_key = _get_random_bytes()
+    encrypted_key = PasswordBasedBytesEncryptor(secret).encrypt(cipher_key)
+    with open_new_securely_permissioned_file(key_file_path, "wb") as f:
+        f.write(encrypted_key)
+    return KeyBasedEncryptor(cipher_key)
+
+
+def _get_random_bytes() -> bytes:
+    return Random.new().read(_BLOCK_SIZE)
+
+
+def remove_old_datastore_key(key_file_dir: str):
+    key_file_path = _get_key_file_path(key_file_dir)
+    if os.path.isfile(key_file_path):
+        os.remove(key_file_path)
+
+
+def initialize_datastore_encryptor(key_file_dir: str, secret: str):
     global _encryptor
 
-    _encryptor = DataStoreEncryptor(key_file_dir)
+    key_file_path = _get_key_file_path(key_file_dir)
+    if os.path.exists(key_file_path):
+        _encryptor = _load_existing_key(key_file_path, secret)
+    else:
+        _encryptor = _create_new_key(key_file_path, secret)
 
 
-def get_datastore_encryptor():
+def _get_key_file_path(key_file_dir: str) -> str:
+    return os.path.join(key_file_dir, _KEY_FILENAME)
+
+
+def get_datastore_encryptor() -> IEncryptor:
     return _encryptor
diff --git a/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/mimikatz_results_encryptor.py b/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/mimikatz_results_encryptor.py
index 6261f5147..ff2ee314e 100644
--- a/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/mimikatz_results_encryptor.py
+++ b/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/mimikatz_results_encryptor.py
@@ -17,7 +17,7 @@ class MimikatzResultsEncryptor(IFieldEncryptor):
         for _, credentials in results.items():
             for secret_type in MimikatzResultsEncryptor.secret_types:
                 try:
-                    credentials[secret_type] = get_datastore_encryptor().enc(
+                    credentials[secret_type] = get_datastore_encryptor().encrypt(
                         credentials[secret_type]
                     )
                 except ValueError as e:
@@ -25,12 +25,14 @@ class MimikatzResultsEncryptor(IFieldEncryptor):
                         f"Failed encrypting sensitive field for "
                         f"user {credentials['username']}! Error: {e}"
                     )
-                    credentials[secret_type] = get_datastore_encryptor().enc("")
+                    credentials[secret_type] = get_datastore_encryptor().encrypt("")
         return results
 
     @staticmethod
     def decrypt(results: dict) -> dict:
         for _, credentials in results.items():
             for secret_type in MimikatzResultsEncryptor.secret_types:
-                credentials[secret_type] = get_datastore_encryptor().dec(credentials[secret_type])
+                credentials[secret_type] = get_datastore_encryptor().decrypt(
+                    credentials[secret_type]
+                )
         return results
diff --git a/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/string_list_encryptor.py b/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/string_list_encryptor.py
index 46eef09cb..04374c462 100644
--- a/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/string_list_encryptor.py
+++ b/monkey/monkey_island/cc/server_utils/encryption/dict_encryption/field_encryptors/string_list_encryptor.py
@@ -9,8 +9,8 @@ from monkey_island.cc.server_utils.encryption.dict_encryption.field_encryptors i
 class StringListEncryptor(IFieldEncryptor):
     @staticmethod
     def encrypt(value: List[str]):
-        return [get_datastore_encryptor().enc(string) for string in value]
+        return [get_datastore_encryptor().encrypt(string) for string in value]
 
     @staticmethod
     def decrypt(value: List[str]):
-        return [get_datastore_encryptor().dec(string) for string in value]
+        return [get_datastore_encryptor().decrypt(string) for string in value]
diff --git a/monkey/monkey_island/cc/server_utils/encryption/encryptors/__init__.py b/monkey/monkey_island/cc/server_utils/encryption/encryptors/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/monkey/monkey_island/cc/server_utils/encryption/i_encryptor.py b/monkey/monkey_island/cc/server_utils/encryption/encryptors/i_encryptor.py
similarity index 100%
rename from monkey/monkey_island/cc/server_utils/encryption/i_encryptor.py
rename to monkey/monkey_island/cc/server_utils/encryption/encryptors/i_encryptor.py
diff --git a/monkey/monkey_island/cc/server_utils/encryption/key_based_encryptor.py b/monkey/monkey_island/cc/server_utils/encryption/encryptors/key_based_encryptor.py
similarity index 100%
rename from monkey/monkey_island/cc/server_utils/encryption/key_based_encryptor.py
rename to monkey/monkey_island/cc/server_utils/encryption/encryptors/key_based_encryptor.py
diff --git a/monkey/monkey_island/cc/server_utils/encryption/password_based_encryption.py b/monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_bytes_encryption.py
similarity index 66%
rename from monkey/monkey_island/cc/server_utils/encryption/password_based_encryption.py
rename to monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_bytes_encryption.py
index 20708ce31..2e7c05819 100644
--- a/monkey/monkey_island/cc/server_utils/encryption/password_based_encryption.py
+++ b/monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_bytes_encryption.py
@@ -1,4 +1,3 @@
-import base64
 import io
 import logging
 
@@ -17,36 +16,30 @@ logger = logging.getLogger(__name__)
 # Note: password != key
 
 
-class PasswordBasedEncryptor(IEncryptor):
+class PasswordBasedBytesEncryptor(IEncryptor):
 
     _BUFFER_SIZE = pyAesCrypt.crypto.bufferSizeDef
 
     def __init__(self, password: str):
         self.password = password
 
-    def encrypt(self, plaintext: str) -> str:
-        plaintext_stream = io.BytesIO(plaintext.encode())
+    def encrypt(self, plaintext: bytes) -> bytes:
         ciphertext_stream = io.BytesIO()
 
         pyAesCrypt.encryptStream(
-            plaintext_stream, ciphertext_stream, self.password, self._BUFFER_SIZE
+            io.BytesIO(plaintext), ciphertext_stream, self.password, self._BUFFER_SIZE
         )
 
-        ciphertext_b64 = base64.b64encode(ciphertext_stream.getvalue())
-        logger.info("String encrypted.")
+        return ciphertext_stream.getvalue()
 
-        return ciphertext_b64.decode()
-
-    def decrypt(self, ciphertext: str):
-        ciphertext = base64.b64decode(ciphertext)
-        ciphertext_stream = io.BytesIO(ciphertext)
+    def decrypt(self, ciphertext: bytes) -> bytes:
         plaintext_stream = io.BytesIO()
 
-        ciphertext_stream_len = len(ciphertext_stream.getvalue())
+        ciphertext_stream_len = len(ciphertext)
 
         try:
             pyAesCrypt.decryptStream(
-                ciphertext_stream,
+                io.BytesIO(ciphertext),
                 plaintext_stream,
                 self.password,
                 self._BUFFER_SIZE,
@@ -59,7 +52,7 @@ class PasswordBasedEncryptor(IEncryptor):
             else:
                 logger.info("The corrupt ciphertext provided.")
                 raise InvalidCiphertextError
-        return plaintext_stream.getvalue().decode("utf-8")
+        return plaintext_stream.getvalue()
 
 
 class InvalidCredentialsError(Exception):
@@ -68,8 +61,3 @@ class InvalidCredentialsError(Exception):
 
 class InvalidCiphertextError(Exception):
     """ Raised when ciphertext is corrupted """
-
-
-def is_encrypted(ciphertext: str) -> bool:
-    ciphertext = base64.b64decode(ciphertext)
-    return ciphertext.startswith(b"AES")
diff --git a/monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_string_encryptior.py b/monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_string_encryptior.py
new file mode 100644
index 000000000..9f99f735b
--- /dev/null
+++ b/monkey/monkey_island/cc/server_utils/encryption/encryptors/password_based_string_encryptior.py
@@ -0,0 +1,35 @@
+import base64
+import logging
+
+import pyAesCrypt
+
+from monkey_island.cc.server_utils.encryption import IEncryptor
+from monkey_island.cc.server_utils.encryption.encryptors.password_based_bytes_encryption import (
+    PasswordBasedBytesEncryptor,
+)
+
+logger = logging.getLogger(__name__)
+
+
+class PasswordBasedStringEncryptor(IEncryptor):
+
+    _BUFFER_SIZE = pyAesCrypt.crypto.bufferSizeDef
+
+    def __init__(self, password: str):
+        self.password = password
+
+    def encrypt(self, plaintext: str) -> str:
+        ciphertext = PasswordBasedBytesEncryptor(self.password).encrypt(plaintext.encode())
+
+        return base64.b64encode(ciphertext).decode()
+
+    def decrypt(self, ciphertext: str) -> str:
+        ciphertext = base64.b64decode(ciphertext)
+
+        plaintext_stream = PasswordBasedBytesEncryptor(self.password).decrypt(ciphertext)
+        return plaintext_stream.decode()
+
+
+def is_encrypted(ciphertext: str) -> bool:
+    ciphertext = base64.b64decode(ciphertext)
+    return ciphertext.startswith(b"AES")
diff --git a/monkey/monkey_island/cc/services/attack/technique_reports/technique_report_tools.py b/monkey/monkey_island/cc/services/attack/technique_reports/technique_report_tools.py
index 16884678b..5bb61bc14 100644
--- a/monkey/monkey_island/cc/services/attack/technique_reports/technique_report_tools.py
+++ b/monkey/monkey_island/cc/services/attack/technique_reports/technique_report_tools.py
@@ -29,7 +29,7 @@ def censor_password(password, plain_chars=3, secret_chars=5):
     """
     if not password:
         return ""
-    password = get_datastore_encryptor().dec(password)
+    password = get_datastore_encryptor().decrypt(password)
     return password[0:plain_chars] + "*" * secret_chars
 
 
@@ -42,5 +42,5 @@ def censor_hash(hash_, plain_chars=5):
     """
     if not hash_:
         return ""
-    hash_ = get_datastore_encryptor().dec(hash_)
+    hash_ = get_datastore_encryptor().decrypt(hash_)
     return hash_[0:plain_chars] + " ..."
diff --git a/monkey/monkey_island/cc/services/authentication.py b/monkey/monkey_island/cc/services/authentication.py
new file mode 100644
index 000000000..9d3d3baa7
--- /dev/null
+++ b/monkey/monkey_island/cc/services/authentication.py
@@ -0,0 +1,35 @@
+from monkey_island.cc.server_utils.encryption import (
+    get_datastore_encryptor,
+    initialize_datastore_encryptor,
+    remove_old_datastore_key,
+)
+
+
+class AuthenticationService:
+    KEY_FILE_DIRECTORY = None
+
+    # TODO: A number of these services should be instance objects instead of
+    # static/singleton hybrids. At the moment, this requires invasive refactoring that's
+    # not a priority.
+    @classmethod
+    def initialize(cls, key_file_directory):
+        cls.KEY_FILE_DIRECTORY = key_file_directory
+
+    @staticmethod
+    def ensure_datastore_encryptor(username: str, password: str):
+        if not get_datastore_encryptor():
+            AuthenticationService._init_encryptor_from_credentials(username, password)
+
+    @staticmethod
+    def reset_datastore_encryptor(username: str, password: str):
+        remove_old_datastore_key(AuthenticationService.KEY_FILE_DIRECTORY)
+        AuthenticationService._init_encryptor_from_credentials(username, password)
+
+    @staticmethod
+    def _init_encryptor_from_credentials(username: str, password: str):
+        secret = AuthenticationService._get_secret_from_credentials(username, password)
+        initialize_datastore_encryptor(AuthenticationService.KEY_FILE_DIRECTORY, secret)
+
+    @staticmethod
+    def _get_secret_from_credentials(username: str, password: str) -> str:
+        return f"{username}:{password}"
diff --git a/monkey/monkey_island/cc/services/config.py b/monkey/monkey_island/cc/services/config.py
index 973ca104a..6ddcd896f 100644
--- a/monkey/monkey_island/cc/services/config.py
+++ b/monkey/monkey_island/cc/services/config.py
@@ -90,9 +90,9 @@ class ConfigService:
         if should_decrypt:
             if config_key_as_arr in ENCRYPTED_CONFIG_VALUES:
                 if isinstance(config, str):
-                    config = get_datastore_encryptor().dec(config)
+                    config = get_datastore_encryptor().decrypt(config)
                 elif isinstance(config, list):
-                    config = [get_datastore_encryptor().dec(x) for x in config]
+                    config = [get_datastore_encryptor().decrypt(x) for x in config]
         return config
 
     @staticmethod
@@ -130,7 +130,7 @@ class ConfigService:
         if item_value in items_from_config:
             return
         if should_encrypt:
-            item_value = get_datastore_encryptor().enc(item_value)
+            item_value = get_datastore_encryptor().encrypt(item_value)
         mongo.db.config.update(
             {"name": "newconfig"}, {"$addToSet": {item_key: item_value}}, upsert=False
         )
@@ -350,10 +350,10 @@ class ConfigService:
                     ]
                 else:
                     flat_config[key] = [
-                        get_datastore_encryptor().dec(item) for item in flat_config[key]
+                        get_datastore_encryptor().decrypt(item) for item in flat_config[key]
                     ]
             else:
-                flat_config[key] = get_datastore_encryptor().dec(flat_config[key])
+                flat_config[key] = get_datastore_encryptor().decrypt(flat_config[key])
         return flat_config
 
     @staticmethod
@@ -379,25 +379,25 @@ class ConfigService:
                         )
                     else:
                         config_arr[i] = (
-                            get_datastore_encryptor().dec(config_arr[i])
+                            get_datastore_encryptor().decrypt(config_arr[i])
                             if is_decrypt
-                            else get_datastore_encryptor().enc(config_arr[i])
+                            else get_datastore_encryptor().encrypt(config_arr[i])
                         )
             else:
                 parent_config_arr[config_arr_as_array[-1]] = (
-                    get_datastore_encryptor().dec(config_arr)
+                    get_datastore_encryptor().decrypt(config_arr)
                     if is_decrypt
-                    else get_datastore_encryptor().enc(config_arr)
+                    else get_datastore_encryptor().encrypt(config_arr)
                 )
 
     @staticmethod
     def decrypt_ssh_key_pair(pair, encrypt=False):
         if encrypt:
-            pair["public_key"] = get_datastore_encryptor().enc(pair["public_key"])
-            pair["private_key"] = get_datastore_encryptor().enc(pair["private_key"])
+            pair["public_key"] = get_datastore_encryptor().encrypt(pair["public_key"])
+            pair["private_key"] = get_datastore_encryptor().encrypt(pair["private_key"])
         else:
-            pair["public_key"] = get_datastore_encryptor().dec(pair["public_key"])
-            pair["private_key"] = get_datastore_encryptor().dec(pair["private_key"])
+            pair["public_key"] = get_datastore_encryptor().decrypt(pair["public_key"])
+            pair["private_key"] = get_datastore_encryptor().decrypt(pair["private_key"])
         return pair
 
     @staticmethod
diff --git a/monkey/monkey_island/cc/services/database.py b/monkey/monkey_island/cc/services/database.py
index afd4ecc02..fb46cd726 100644
--- a/monkey/monkey_island/cc/services/database.py
+++ b/monkey/monkey_island/cc/services/database.py
@@ -33,11 +33,6 @@ class Database(object):
         mongo.db[collection_name].drop()
         logger.info("Dropped collection {}".format(collection_name))
 
-    @staticmethod
-    def init_db():
-        if not mongo.db.collection_names():
-            Database.reset_db()
-
     @staticmethod
     def is_mitigations_missing() -> bool:
         return bool(AttackMitigations.COLLECTION_NAME not in mongo.db.list_collection_names())
diff --git a/monkey/monkey_island/cc/services/initialize.py b/monkey/monkey_island/cc/services/initialize.py
index 6ff0d2706..b6e37bbc7 100644
--- a/monkey/monkey_island/cc/services/initialize.py
+++ b/monkey/monkey_island/cc/services/initialize.py
@@ -1,3 +1,4 @@
+from monkey_island.cc.services.authentication import AuthenticationService
 from monkey_island.cc.services.post_breach_files import PostBreachFilesService
 from monkey_island.cc.services.run_local_monkey import LocalMonkeyRunService
 
@@ -5,3 +6,4 @@ from monkey_island.cc.services.run_local_monkey import LocalMonkeyRunService
 def initialize_services(data_dir):
     PostBreachFilesService.initialize(data_dir)
     LocalMonkeyRunService.initialize(data_dir)
+    AuthenticationService.initialize(key_file_directory=data_dir)
diff --git a/monkey/monkey_island/cc/services/telemetry/processing/exploit.py b/monkey/monkey_island/cc/services/telemetry/processing/exploit.py
index 7c156930a..e302be5f5 100644
--- a/monkey/monkey_island/cc/services/telemetry/processing/exploit.py
+++ b/monkey/monkey_island/cc/services/telemetry/processing/exploit.py
@@ -76,4 +76,4 @@ def encrypt_exploit_creds(telemetry_json):
             credential = attempts[i][field]
             if credential:  # PowerShell exploiter's telem may have `None` here
                 if len(credential) > 0:
-                    attempts[i][field] = get_datastore_encryptor().enc(credential)
+                    attempts[i][field] = get_datastore_encryptor().encrypt(credential)
diff --git a/monkey/monkey_island/cc/services/telemetry/processing/system_info.py b/monkey/monkey_island/cc/services/telemetry/processing/system_info.py
index ba72e822b..7d7f404ce 100644
--- a/monkey/monkey_island/cc/services/telemetry/processing/system_info.py
+++ b/monkey/monkey_island/cc/services/telemetry/processing/system_info.py
@@ -70,7 +70,7 @@ def encrypt_system_info_ssh_keys(ssh_info):
     for idx, user in enumerate(ssh_info):
         for field in ["public_key", "private_key", "known_hosts"]:
             if ssh_info[idx][field]:
-                ssh_info[idx][field] = get_datastore_encryptor().enc(ssh_info[idx][field])
+                ssh_info[idx][field] = get_datastore_encryptor().encrypt(ssh_info[idx][field])
 
 
 def process_credential_info(telemetry_json):
diff --git a/monkey/monkey_island/cc/services/zero_trust/scoutsuite/scoutsuite_auth_service.py b/monkey/monkey_island/cc/services/zero_trust/scoutsuite/scoutsuite_auth_service.py
index 89aa002fa..b54b3252c 100644
--- a/monkey/monkey_island/cc/services/zero_trust/scoutsuite/scoutsuite_auth_service.py
+++ b/monkey/monkey_island/cc/services/zero_trust/scoutsuite/scoutsuite_auth_service.py
@@ -41,7 +41,7 @@ def set_aws_keys(access_key_id: str, secret_access_key: str, session_token: str)
 
 def _set_aws_key(key_type: str, key_value: str):
     path_to_keys = AWS_KEYS_PATH
-    encrypted_key = get_datastore_encryptor().enc(key_value)
+    encrypted_key = get_datastore_encryptor().encrypt(key_value)
     ConfigService.set_config_value(path_to_keys + [key_type], encrypted_key)
 
 
diff --git a/monkey/monkey_island/cc/ui/src/services/AuthService.js b/monkey/monkey_island/cc/ui/src/services/AuthService.js
index 11cf37044..7838a8563 100644
--- a/monkey/monkey_island/cc/ui/src/services/AuthService.js
+++ b/monkey/monkey_island/cc/ui/src/services/AuthService.js
@@ -46,7 +46,7 @@ export default class AuthService {
     return this._authFetch(this.REGISTRATION_API_ENDPOINT, {
       method: 'POST',
       body: JSON.stringify({
-        'user': username,
+        'username': username,
         'password': password
       })
     }).then(res => {
diff --git a/monkey/tests/data_for_tests/mongo_key.bin b/monkey/tests/data_for_tests/mongo_key.bin
index 6b8091efb..7b49bd4dc 100644
Binary files a/monkey/tests/data_for_tests/mongo_key.bin and b/monkey/tests/data_for_tests/mongo_key.bin differ
diff --git a/monkey/tests/unit_tests/monkey_island/cc/conftest.py b/monkey/tests/unit_tests/monkey_island/cc/conftest.py
index 9cca0caab..7d9642201 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/conftest.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/conftest.py
@@ -11,6 +11,7 @@ from tests.unit_tests.monkey_island.cc.server_utils.encryption.test_password_bas
 )
 
 from monkey_island.cc.server_utils.encryption import initialize_datastore_encryptor
+from monkey_island.cc.services.authentication import AuthenticationService
 
 
 @pytest.fixture
@@ -27,6 +28,11 @@ def monkey_config_json(monkey_config):
     return json.dumps(monkey_config)
 
 
+MOCK_USERNAME = "m0nk3y_u53r"
+MOCK_PASSWORD = "3cr3t_p455w0rd"
+
+
 @pytest.fixture
 def uses_encryptor(data_for_tests_dir):
-    initialize_datastore_encryptor(data_for_tests_dir)
+    secret = AuthenticationService._get_secret_from_credentials(MOCK_USERNAME, MOCK_PASSWORD)
+    initialize_datastore_encryptor(data_for_tests_dir, secret)
diff --git a/monkey/tests/unit_tests/monkey_island/cc/models/utils/field_encryptors/test_string_list_encryptor.py b/monkey/tests/unit_tests/monkey_island/cc/models/utils/field_encryptors/test_string_list_encryptor.py
index d02ad5bbb..7ea21849b 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/models/utils/field_encryptors/test_string_list_encryptor.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/models/utils/field_encryptors/test_string_list_encryptor.py
@@ -1,6 +1,3 @@
-import pytest
-
-from monkey_island.cc.server_utils.encryption import initialize_datastore_encryptor
 from monkey_island.cc.server_utils.encryption.dict_encryption.field_encryptors import (
     StringListEncryptor,
 )
@@ -9,11 +6,6 @@ MOCK_STRING_LIST = ["test_1", "test_2"]
 EMPTY_LIST = []
 
 
-@pytest.fixture
-def uses_encryptor(data_for_tests_dir):
-    initialize_datastore_encryptor(data_for_tests_dir)
-
-
 def test_encryption_and_decryption(uses_encryptor):
     encrypted_list = StringListEncryptor.encrypt(MOCK_STRING_LIST)
     assert not encrypted_list == MOCK_STRING_LIST
diff --git a/monkey/tests/unit_tests/monkey_island/cc/resources/test_configuration_import.py b/monkey/tests/unit_tests/monkey_island/cc/resources/test_configuration_import.py
index fb397f234..bf7ccff80 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/resources/test_configuration_import.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/resources/test_configuration_import.py
@@ -8,7 +8,7 @@ from tests.unit_tests.monkey_island.cc.services.utils.ciphertexts_for_encryption
 
 from common.utils.exceptions import InvalidConfigurationError
 from monkey_island.cc.resources.configuration_import import ConfigurationImport
-from monkey_island.cc.server_utils.encryption import PasswordBasedEncryptor
+from monkey_island.cc.server_utils.encryption import PasswordBasedStringEncryptor
 
 
 def test_is_config_encrypted__json(monkey_config_json):
@@ -17,7 +17,7 @@ def test_is_config_encrypted__json(monkey_config_json):
 
 @pytest.mark.slow
 def test_is_config_encrypted__ciphertext(monkey_config_json):
-    pb_encryptor = PasswordBasedEncryptor(PASSWORD)
+    pb_encryptor = PasswordBasedStringEncryptor(PASSWORD)
     encrypted_config = pb_encryptor.encrypt(monkey_config_json)
     assert ConfigurationImport.is_config_encrypted(encrypted_config)
 
diff --git a/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_data_store_encryptor.py b/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_data_store_encryptor.py
index bb005fbf7..7c379af1c 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_data_store_encryptor.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_data_store_encryptor.py
@@ -1,35 +1,61 @@
-import os
+import pytest
 
 from monkey_island.cc.server_utils.encryption import (
+    data_store_encryptor,
     get_datastore_encryptor,
     initialize_datastore_encryptor,
+    remove_old_datastore_key,
 )
 
-PASSWORD_FILENAME = "mongo_key.bin"
-
 PLAINTEXT = "Hello, Monkey!"
-CYPHERTEXT = "vKgvD6SjRyIh1dh2AM/rnTa0NI/vjfwnbZLbMocWtE4e42WJmSUz2ordtbQrH1Fq"
+MOCK_SECRET = "53CR31"
 
 
-def test_aes_cbc_encryption(data_for_tests_dir):
-    initialize_datastore_encryptor(data_for_tests_dir)
+@pytest.mark.usefixtures("uses_encryptor")
+def test_encryption(data_for_tests_dir):
+    encrypted_data = get_datastore_encryptor().encrypt(PLAINTEXT)
+    assert encrypted_data != PLAINTEXT
 
-    assert get_datastore_encryptor().enc(PLAINTEXT) != PLAINTEXT
+    decrypted_data = get_datastore_encryptor().decrypt(encrypted_data)
+    assert decrypted_data == PLAINTEXT
 
 
-def test_aes_cbc_decryption(data_for_tests_dir):
-    initialize_datastore_encryptor(data_for_tests_dir)
-
-    assert get_datastore_encryptor().dec(CYPHERTEXT) == PLAINTEXT
+@pytest.fixture
+def cleanup_encryptor():
+    yield
+    data_store_encryptor._encryptor = None
 
 
-def test_aes_cbc_enc_dec(data_for_tests_dir):
-    initialize_datastore_encryptor(data_for_tests_dir)
-
-    assert get_datastore_encryptor().dec(get_datastore_encryptor().enc(PLAINTEXT)) == PLAINTEXT
+@pytest.mark.usefixtures("cleanup_encryptor")
+@pytest.fixture
+def initialized_encryptor_dir(tmpdir):
+    initialize_datastore_encryptor(tmpdir, MOCK_SECRET)
+    return tmpdir
 
 
-def test_create_new_password_file(tmpdir):
-    initialize_datastore_encryptor(tmpdir)
+def test_key_creation(initialized_encryptor_dir):
+    assert (initialized_encryptor_dir / data_store_encryptor._KEY_FILENAME).isfile()
 
-    assert os.path.isfile(os.path.join(tmpdir, PASSWORD_FILENAME))
+
+def test_key_removal(initialized_encryptor_dir):
+    remove_old_datastore_key(initialized_encryptor_dir)
+    assert not (initialized_encryptor_dir / data_store_encryptor._KEY_FILENAME).isfile()
+
+
+def test_key_removal__no_key(tmpdir):
+    assert not (tmpdir / data_store_encryptor._KEY_FILENAME).isfile()
+    # Make sure no error thrown when we try to remove an non-existing key
+    remove_old_datastore_key(tmpdir)
+    data_store_encryptor._factory = None
+
+
+@pytest.mark.usefixtures("cleanup_encryptor")
+def test_key_file_encryption(tmpdir, monkeypatch):
+    monkeypatch.setattr(data_store_encryptor, "_get_random_bytes", lambda: PLAINTEXT.encode())
+    initialize_datastore_encryptor(tmpdir, MOCK_SECRET)
+    key_file_path = data_store_encryptor._get_key_file_path(tmpdir)
+    key_file_contents = open(key_file_path, "rb").read()
+    assert not key_file_contents == PLAINTEXT.encode()
+
+    key_based_encryptor = data_store_encryptor._load_existing_key(key_file_path, MOCK_SECRET)
+    assert key_based_encryptor._key == PLAINTEXT.encode()
diff --git a/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_password_based_encryption.py b/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_password_based_encryption.py
index d00609481..a231f3219 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_password_based_encryption.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/server_utils/encryption/test_password_based_encryption.py
@@ -4,7 +4,10 @@ from tests.unit_tests.monkey_island.cc.services.utils.ciphertexts_for_encryption
     VALID_CIPHER_TEXT,
 )
 
-from monkey_island.cc.server_utils.encryption import InvalidCredentialsError, PasswordBasedEncryptor
+from monkey_island.cc.server_utils.encryption import (
+    InvalidCredentialsError,
+    PasswordBasedStringEncryptor,
+)
 
 MONKEY_CONFIGS_DIR_PATH = "monkey_configs"
 STANDARD_PLAINTEXT_MONKEY_CONFIG_FILENAME = "monkey_config_standard.json"
@@ -14,27 +17,27 @@ INCORRECT_PASSWORD = "goodbye321"
 
 @pytest.mark.slow
 def test_encrypt_decrypt_string(monkey_config_json):
-    pb_encryptor = PasswordBasedEncryptor(PASSWORD)
+    pb_encryptor = PasswordBasedStringEncryptor(PASSWORD)
     encrypted_config = pb_encryptor.encrypt(monkey_config_json)
     assert pb_encryptor.decrypt(encrypted_config) == monkey_config_json
 
 
 @pytest.mark.slow
 def test_decrypt_string__wrong_password(monkey_config_json):
-    pb_encryptor = PasswordBasedEncryptor(INCORRECT_PASSWORD)
+    pb_encryptor = PasswordBasedStringEncryptor(INCORRECT_PASSWORD)
     with pytest.raises(InvalidCredentialsError):
         pb_encryptor.decrypt(VALID_CIPHER_TEXT)
 
 
 @pytest.mark.slow
 def test_decrypt_string__malformed_corrupted():
-    pb_encryptor = PasswordBasedEncryptor(PASSWORD)
+    pb_encryptor = PasswordBasedStringEncryptor(PASSWORD)
     with pytest.raises(ValueError):
         pb_encryptor.decrypt(MALFORMED_CIPHER_TEXT_CORRUPTED)
 
 
 @pytest.mark.slow
 def test_decrypt_string__no_password(monkey_config_json):
-    pb_encryptor = PasswordBasedEncryptor("")
+    pb_encryptor = PasswordBasedStringEncryptor("")
     with pytest.raises(InvalidCredentialsError):
         pb_encryptor.decrypt(VALID_CIPHER_TEXT)
diff --git a/monkey/tests/unit_tests/monkey_island/cc/services/reporting/test_report.py b/monkey/tests/unit_tests/monkey_island/cc/services/reporting/test_report.py
index 6829965f2..a16299707 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/services/reporting/test_report.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/services/reporting/test_report.py
@@ -156,7 +156,7 @@ def test_get_stolen_creds_exploit(fake_mongo):
     assert expected_stolen_creds_exploit == stolen_creds_exploit
 
 
-@pytest.mark.usefixtures("uses_database")
+@pytest.mark.usefixtures("uses_database", "uses_encryptor")
 def test_get_stolen_creds_system_info(fake_mongo):
     fake_mongo.db.monkey.insert_one(MONKEY_TELEM)
     save_telemetry(SYSTEM_INFO_TELEMETRY_TELEM)
diff --git a/monkey/tests/unit_tests/monkey_island/cc/services/test_config.py b/monkey/tests/unit_tests/monkey_island/cc/services/test_config.py
index 799fc40e1..75b3152e5 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/services/test_config.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/services/test_config.py
@@ -18,12 +18,14 @@ def mock_port_in_env_singleton(monkeypatch, PORT):
     monkeypatch.setattr("monkey_island.cc.services.config.env_singleton", mock_singleton)
 
 
+@pytest.mark.usefixtures("uses_encryptor")
 def test_set_server_ips_in_config_command_servers(config, IPS, PORT):
     ConfigService.set_server_ips_in_config(config)
     expected_config_command_servers = [f"{ip}:{PORT}" for ip in IPS]
     assert config["internal"]["island_server"]["command_servers"] == expected_config_command_servers
 
 
+@pytest.mark.usefixtures("uses_encryptor")
 def test_set_server_ips_in_config_current_server(config, IPS, PORT):
     ConfigService.set_server_ips_in_config(config)
     expected_config_current_server = f"{IPS[0]}:{PORT}"
diff --git a/monkey/tests/unit_tests/monkey_island/cc/services/test_config_manipulator.py b/monkey/tests/unit_tests/monkey_island/cc/services/test_config_manipulator.py
index 12cd44c10..1935d6f79 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/services/test_config_manipulator.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/services/test_config_manipulator.py
@@ -1,7 +1,10 @@
+import pytest
+
 from monkey_island.cc.services.config_manipulator import update_config_on_mode_set
 from monkey_island.cc.services.mode.mode_enum import IslandModeEnum
 
 
+@pytest.mark.usefixtures("uses_encryptor")
 def test_update_config_on_mode_set_advanced(config, monkeypatch):
     monkeypatch.setattr("monkey_island.cc.services.config.ConfigService.get_config", lambda: config)
     monkeypatch.setattr(
@@ -14,6 +17,7 @@ def test_update_config_on_mode_set_advanced(config, monkeypatch):
     assert manipulated_config == config
 
 
+@pytest.mark.usefixtures("uses_encryptor")
 def test_update_config_on_mode_set_ransomware(config, monkeypatch):
     monkeypatch.setattr("monkey_island.cc.services.config.ConfigService.get_config", lambda: config)
     monkeypatch.setattr(
diff --git a/monkey/tests/unit_tests/monkey_island/cc/services/zero_trust/scoutsuite/test_scoutsuite_auth_service.py b/monkey/tests/unit_tests/monkey_island/cc/services/zero_trust/scoutsuite/test_scoutsuite_auth_service.py
index 2e6c2fd50..974377915 100644
--- a/monkey/tests/unit_tests/monkey_island/cc/services/zero_trust/scoutsuite/test_scoutsuite_auth_service.py
+++ b/monkey/tests/unit_tests/monkey_island/cc/services/zero_trust/scoutsuite/test_scoutsuite_auth_service.py
@@ -5,10 +5,7 @@ import pytest
 
 from common.config_value_paths import AWS_KEYS_PATH
 from monkey_island.cc.database import mongo
-from monkey_island.cc.server_utils.encryption import (
-    get_datastore_encryptor,
-    initialize_datastore_encryptor,
-)
+from monkey_island.cc.server_utils.encryption import get_datastore_encryptor
 from monkey_island.cc.services.config import ConfigService
 from monkey_island.cc.services.zero_trust.scoutsuite.scoutsuite_auth_service import (
     is_aws_keys_setup,
@@ -19,7 +16,7 @@ class MockObject:
     pass
 
 
-@pytest.mark.usefixtures("uses_database")
+@pytest.mark.usefixtures("uses_database", "uses_encryptor")
 def test_is_aws_keys_setup(tmp_path):
     # Mock default configuration
     ConfigService.init_default_config()
@@ -29,9 +26,7 @@ def test_is_aws_keys_setup(tmp_path):
     mongo.db.config.find_one = MagicMock(return_value=ConfigService.default_config)
     assert not is_aws_keys_setup()
 
-    # Make sure noone changed config path and broke this function
-    initialize_datastore_encryptor(tmp_path)
-    bogus_key_value = get_datastore_encryptor().enc("bogus_aws_key")
+    bogus_key_value = get_datastore_encryptor().encrypt("bogus_aws_key")
     dpath.util.set(
         ConfigService.default_config, AWS_KEYS_PATH + ["aws_secret_access_key"], bogus_key_value
     )