diff --git a/skywipe/auth.py b/skywipe/auth.py
index e692bf1..d6addf3 100644
--- a/skywipe/auth.py
+++ b/skywipe/auth.py
@@ -10,7 +10,11 @@ class Auth:
         self.client = None
 
     def login(self) -> Client:
-        config_data = self.config.load()
+        try:
+            config_data = self.config.load()
+        except FileNotFoundError as e:
+            raise ValueError(
+                "Configuration file not found. Run 'skywipe configure' first.") from e
 
         handle = config_data.get("handle")
         password = config_data.get("password")
@@ -19,7 +23,11 @@ class Auth:
             raise ValueError(
                 "handle and password must be set in configuration")
 
-        self.client = Client()
-        self.client.login(handle, password)
+        try:
+            self.client = Client()
+            self.client.login(handle, password)
+        except Exception as e:
+            raise ValueError(
+                f"Failed to authenticate: {e}") from e
 
         return self.client
diff --git a/skywipe/commands.py b/skywipe/commands.py
index 937ee28..13a647c 100644
--- a/skywipe/commands.py
+++ b/skywipe/commands.py
@@ -63,12 +63,22 @@ def _create_operation_handler(
 ) -> CommandHandler:
     def handler(skip_confirmation: bool = False):
         require_confirmation(confirmation_message, skip_confirmation)
-        Operation(
-            operation_name,
-            strategy_type=strategy_type,
-            collection=collection,
-            filter_fn=filter_fn
-        ).run()
+        try:
+            Operation(
+                operation_name,
+                strategy_type=strategy_type,
+                collection=collection,
+                filter_fn=filter_fn
+            ).run()
+        except ValueError as e:
+            logger = get_logger()
+            logger.error(f"{e}")
+            raise
+        except Exception as e:
+            logger = get_logger()
+            logger.error(
+                f"Unexpected error during operation: {e}", exc_info=True)
+            raise
     return handler
 
 
diff --git a/skywipe/configure.py b/skywipe/configure.py
index cb69bc7..df2cdce 100644
--- a/skywipe/configure.py
+++ b/skywipe/configure.py
@@ -51,8 +51,12 @@ class Configuration:
             "verbose": verbose
         }
 
-        with open(self.config_file, "w") as f:
-            yaml.dump(config_data, f, default_flow_style=False)
+        try:
+            with open(self.config_file, "w") as f:
+                yaml.dump(config_data, f, default_flow_style=False)
+        except (IOError, OSError) as e:
+            logger.error(f"Failed to save configuration: {e}")
+            return
 
         logger.info(f"Configuration saved to {self.config_file}")
 
@@ -60,5 +64,15 @@ class Configuration:
         if not self.exists():
             raise FileNotFoundError(
                 f"Configuration file not found: {self.config_file}")
-        with open(self.config_file, "r") as f:
-            return yaml.safe_load(f)
+        try:
+            with open(self.config_file, "r") as f:
+                config_data = yaml.safe_load(f)
+                if config_data is None:
+                    raise ValueError("Configuration file is empty or invalid")
+                return config_data
+        except (IOError, OSError) as e:
+            raise ValueError(
+                f"Failed to read configuration file: {e}") from e
+        except yaml.YAMLError as e:
+            raise ValueError(
+                f"Invalid YAML in configuration file: {e}") from e
diff --git a/skywipe/operations.py b/skywipe/operations.py
index 113b589..601c516 100644
--- a/skywipe/operations.py
+++ b/skywipe/operations.py
@@ -12,10 +12,20 @@ from .logger import get_logger, ProgressTracker
 class OperationContext:
     def __init__(self):
         self.logger = get_logger()
-        self.auth = Auth()
-        self.client = self.auth.login()
-        self.config = Configuration()
-        self.config_data = self.config.load()
+        try:
+            self.auth = Auth()
+            self.client = self.auth.login()
+            self.config = Configuration()
+            self.config_data = self.config.load()
+        except (ValueError, FileNotFoundError) as e:
+            self.logger.error(f"Configuration error: {e}")
+            raise
+        except Exception as e:
+            self.logger.error(
+                f"Unexpected error during initialization: {e}", exc_info=True)
+            raise ValueError(
+                f"Failed to initialize operation context: {e}") from e
+
         self.batch_size = self.config_data.get("batch_size", 10)
         self.delay = self.config_data.get("delay", 1)
         self.did = self.client.me.did
@@ -138,8 +148,13 @@ class Operation:
 
         while True:
             batch_num += 1
-            response = self.strategy.fetch(context, cursor)
-            items = self.strategy.extract_items(response)
+            try:
+                response = self.strategy.fetch(context, cursor)
+                items = self.strategy.extract_items(response)
+            except Exception as e:
+                context.logger.error(
+                    f"Error fetching items for batch {batch_num}: {e}", exc_info=True)
+                break
 
             if not items:
                 break