diff --git a/nucypher/cli/actions/select.py b/nucypher/cli/actions/select.py
index e4b6f764b..ec6d51327 100644
--- a/nucypher/cli/actions/select.py
+++ b/nucypher/cli/actions/select.py
@@ -14,9 +14,11 @@ from nucypher.cli.actions.migrate import migrate
 from nucypher.cli.literature import (
     DEFAULT_TO_LONE_CONFIG_FILE,
     GENERIC_SELECT_ACCOUNT,
+    IGNORE_OLD_CONFIGURATION,
     MIGRATE_OLD_CONFIGURATION,
     NO_ACCOUNTS,
     NO_CONFIGURATIONS_ON_DISK,
+    PROMPT_TO_MIGRATE,
     SELECT_DOMAIN,
     SELECTED_ACCOUNT,
 )
@@ -117,11 +119,13 @@ def select_domain(emitter: StdoutEmitter, message: Optional[str] = None) -> str:
     return domain
 
 
-def select_config_file(emitter: StdoutEmitter,
-                       config_class: Type[CharacterConfiguration],
-                       config_root: Optional[Path] = None,
-                       checksum_address: str = None,
-                       ) -> Path:
+def select_config_file(
+    emitter: StdoutEmitter,
+    config_class: Type[CharacterConfiguration],
+    config_root: Optional[Path] = None,
+    checksum_address: str = None,
+    do_auto_migrate: bool = False,
+) -> Path:
     """
     Selects a nucypher character configuration file from the disk automatically or interactively.
 
@@ -136,6 +140,10 @@ def select_config_file(emitter: StdoutEmitter,
     - If there are multiple character configurations on the disk in the same configuration root,
       use interactive selection.
 
+    - If the configuration file is old and:
+        1. `do_auto_migration` is False then prompt user
+        2. `do_auto_migration` is True then try migrating the file, and retry loading
+
     - Aborts if there are no configurations associated with the supplied character configuration class.
 
     """
@@ -165,14 +173,27 @@ def select_config_file(emitter: StdoutEmitter,
             parsed_config_files.append(fp)
             parsed_addresses_and_filenames.append([config_checksum_address, Path(fp).name])  # store checksum & filename
         except config_class.OldVersion as e:
-            # attempt migration
-            emitter.echo(
-                MIGRATE_OLD_CONFIGURATION.format(config_file=fp, version=e.version),
-                color="yellow",
-            )
-            migrate(emitter=emitter, config_file=fp)
-            # retry migrated file
-            continue
+            attempt_migration = True
+            if not do_auto_migrate:
+                if not click.confirm(
+                    PROMPT_TO_MIGRATE.format(config_file=fp, version=e.version)
+                ):
+                    emitter.echo(
+                        IGNORE_OLD_CONFIGURATION.format(
+                            config_file=fp, version=e.version
+                        ),
+                        color="yellow",
+                    )
+                    attempt_migration = False
+
+            if attempt_migration:
+                emitter.echo(
+                    MIGRATE_OLD_CONFIGURATION.format(config_file=fp, version=e.version),
+                    color="yellow",
+                )
+                migrate(emitter=emitter, config_file=fp)
+                # retry reading migrated file
+                continue
 
         i += 1
 
diff --git a/nucypher/cli/commands/ursula.py b/nucypher/cli/commands/ursula.py
index d5e7e6be2..783a4b9cb 100644
--- a/nucypher/cli/commands/ursula.py
+++ b/nucypher/cli/commands/ursula.py
@@ -120,9 +120,12 @@ class UrsulaConfigOptions:
             )
         else:
             if not config_file:
-                config_file = select_config_file(emitter=emitter,
-                                                 checksum_address=self.operator_address,
-                                                 config_class=UrsulaConfiguration)
+                config_file = select_config_file(
+                    emitter=emitter,
+                    checksum_address=self.operator_address,
+                    config_class=UrsulaConfiguration,
+                    do_auto_migrate=True,
+                )
             try:
                 return UrsulaConfiguration.from_configuration_file(
                     emitter=emitter,
diff --git a/nucypher/cli/literature.py b/nucypher/cli/literature.py
index 1a622c884..64006a581 100644
--- a/nucypher/cli/literature.py
+++ b/nucypher/cli/literature.py
@@ -38,9 +38,17 @@ SUCCESSFUL_DESTRUCTION = "Successfully destroyed nucypher configuration"
 CONFIRM_FORGET_NODES = "Permanently delete all known node data?"
 SUCCESSFUL_FORGET_NODES = "Removed all stored known nodes metadata and certificates"
 
+IGNORE_OLD_CONFIGURATION = """
+Ignoring configuration file '{config_file}' whose version is too old ('{version}').
+Run `nucypher ursula config migrate --config-file '{config_file}'` to update it.
+"""
 MIGRATE_OLD_CONFIGURATION = """
 Migrating configuration file '{config_file}' whose version ('{version}') is too old.
 """
+PROMPT_TO_MIGRATE = """
+Detected configuration file '{config_file}' with old version ('{version}'). Would you 
+like to migrate this file to the newest version? 
+"""
 DEFAULT_TO_LONE_CONFIG_FILE = "Defaulting to {config_class} configuration file: '{config_file}'"
 
 #  Authentication