Improve password retry flow

src/password_manager/manager.py

@@ -377,51 +377,61 @@ class PasswordManager:
     ) -> bool:
         """Set up encryption for the current fingerprint and load the seed."""
 
-        try:
-            if password is None:
-                password = prompt_existing_password("Enter your master password: ")
-
-            iterations = (
-                self.config_manager.get_kdf_iterations()
-                if getattr(self, "config_manager", None)
-                else 100_000
-            )
-            print("Deriving key...")
-            seed_key = derive_key_from_password(password, iterations=iterations)
-            seed_mgr = EncryptionManager(seed_key, fingerprint_dir)
-            print("Decrypting seed...")
+        attempts = 0
+        max_attempts = 5
+        while attempts < max_attempts:
             try:
-                self.parent_seed = seed_mgr.decrypt_parent_seed()
-            except Exception:
-                msg = "Invalid password for selected seed profile."
-                print(colored(msg, "red"))
+                if password is None:
+                    password = prompt_existing_password("Enter your master password: ")
+
+                iterations = (
+                    self.config_manager.get_kdf_iterations()
+                    if getattr(self, "config_manager", None)
+                    else 100_000
+                )
+                print("Deriving key...")
+                seed_key = derive_key_from_password(password, iterations=iterations)
+                seed_mgr = EncryptionManager(seed_key, fingerprint_dir)
+                print("Decrypting seed...")
+                try:
+                    self.parent_seed = seed_mgr.decrypt_parent_seed()
+                except Exception:
+                    msg = (
+                        "Invalid password for selected seed profile. Please try again."
+                    )
+                    print(colored(msg, "red"))
+                    attempts += 1
+                    password = None
+                    continue
+
+                key = derive_index_key(self.parent_seed)
+
+                self.encryption_manager = EncryptionManager(key, fingerprint_dir)
+                self.vault = Vault(self.encryption_manager, fingerprint_dir)
+
+                self.config_manager = ConfigManager(
+                    vault=self.vault,
+                    fingerprint_dir=fingerprint_dir,
+                )
+
+                self.fingerprint_dir = fingerprint_dir
+                if not self.verify_password(password):
+                    print(colored("Invalid password. Please try again.", "red"))
+                    attempts += 1
+                    password = None
+                    continue
+                return True
+            except KeyboardInterrupt:
+                raise
+            except Exception as e:
+                logger.error(f"Failed to set up EncryptionManager: {e}", exc_info=True)
+                print(colored(f"Error: Failed to set up encryption: {e}", "red"))
                 if exit_on_fail:
                     sys.exit(1)
                 return False
-
-            key = derive_index_key(self.parent_seed)
-
-            self.encryption_manager = EncryptionManager(key, fingerprint_dir)
-            self.vault = Vault(self.encryption_manager, fingerprint_dir)
-
-            self.config_manager = ConfigManager(
-                vault=self.vault,
-                fingerprint_dir=fingerprint_dir,
-            )
-
-            self.fingerprint_dir = fingerprint_dir
-            if not self.verify_password(password):
-                print(colored("Invalid password.", "red"))
-                if exit_on_fail:
-                    sys.exit(1)
-                return False
-            return True
-        except Exception as e:
-            logger.error(f"Failed to set up EncryptionManager: {e}", exc_info=True)
-            print(colored(f"Error: Failed to set up encryption: {e}", "red"))
-            if exit_on_fail:
-                sys.exit(1)
-            return False
+        if exit_on_fail:
+            sys.exit(1)
+        return False
 
     def load_parent_seed(
         self, fingerprint_dir: Path, password: Optional[str] = None

src/utils/password_prompt.py

@@ -106,44 +106,55 @@ def prompt_new_password() -> str:
     raise PasswordPromptError("Maximum password attempts exceeded")
 
 
-def prompt_existing_password(prompt_message: str = "Enter your password: ") -> str:
+def prompt_existing_password(
+    prompt_message: str = "Enter your password: ", max_retries: int = 5
+) -> str:
     """
-    Prompts the user to enter an existing password, typically used for decryption purposes.
+    Prompt the user for an existing password.
 
-    This function ensures that the password is entered securely without echoing it to the terminal.
+    The user will be reprompted on empty input up to ``max_retries`` times.
 
     Parameters:
-        prompt_message (str): The message displayed to prompt the user. Defaults to "Enter your password: ".
+        prompt_message (str): Message displayed when prompting for the password.
+        max_retries (int): Number of attempts allowed before aborting.
 
     Returns:
-        str: The password entered by the user.
+        str: The password provided by the user.
 
     Raises:
-        PasswordPromptError: If the user interrupts the operation.
+        PasswordPromptError: If the user interrupts the operation or exceeds
+            ``max_retries`` attempts.
     """
-    try:
-        password = getpass.getpass(prompt=prompt_message).strip()
+    attempts = 0
+    while attempts < max_retries:
+        try:
+            password = getpass.getpass(prompt=prompt_message).strip()
 
-        if not password:
-            print(colored("Error: Password cannot be empty.", "red"))
-            logging.warning("User attempted to enter an empty password.")
-            raise PasswordPromptError("Password cannot be empty")
+            if not password:
+                print(
+                    colored("Error: Password cannot be empty. Please try again.", "red")
+                )
+                logging.warning("User attempted to enter an empty password.")
+                attempts += 1
+                continue
 
-        # Normalize the password to NFKD form
-        normalized_password = unicodedata.normalize("NFKD", password)
-        logging.debug("User entered an existing password for decryption.")
-        return normalized_password
+            normalized_password = unicodedata.normalize("NFKD", password)
+            logging.debug("User entered an existing password for decryption.")
+            return normalized_password
 
-    except KeyboardInterrupt:
-        print(colored("\nOperation cancelled by user.", "yellow"))
-        logging.info("Existing password prompt interrupted by user.")
-        raise PasswordPromptError("Operation cancelled by user")
-    except Exception as e:
-        logging.error(
-            f"Unexpected error during existing password prompt: {e}", exc_info=True
-        )
-        print(colored(f"Error: {e}", "red"))
-        raise PasswordPromptError(str(e))
+        except KeyboardInterrupt:
+            print(colored("\nOperation cancelled by user.", "yellow"))
+            logging.info("Existing password prompt interrupted by user.")
+            raise PasswordPromptError("Operation cancelled by user")
+        except Exception as e:
+            logging.error(
+                f"Unexpected error during existing password prompt: {e}",
+                exc_info=True,
+            )
+            print(colored(f"Error: {e}", "red"))
+            attempts += 1
+
+    raise PasswordPromptError("Maximum password attempts exceeded")
 
 
 def confirm_action(