diff --git a/config/settings.py b/config/settings.py
index 2a14913..6f72f7d 100644
--- a/config/settings.py
+++ b/config/settings.py
@@ -43,6 +43,8 @@ def load_config():
         "project_root": os.getenv("CLOVER_PROJECT_ROOT", "."),
         "summary_file": os.getenv("CLOVER_SUMMARY_FILE", "clover.md"),
         "structure_file": os.getenv("CLOVER_STRUCTURE_FILE", "structure.md"),
+        "max_retries": int(os.getenv("CLOVER_MAX_RETRIES", "3")),
+        "retry_base_delay": float(os.getenv("CLOVER_RETRY_BASE_DELAY", "2")),
     }
 
     # Debug output if enabled
diff --git a/models/api_client.py b/models/api_client.py
index 6e531e2..5e2d61d 100644
--- a/models/api_client.py
+++ b/models/api_client.py
@@ -5,6 +5,7 @@ Handles communication with the OpenAI-compatible LLM server
 
 import json
 import os
+import time
 from typing import Any, Dict, Optional
 
 import requests
@@ -27,7 +28,10 @@ class APIClient:
         self, endpoint: str, method: str = "GET", data: Optional[Dict] = None
     ) -> Dict[str, Any]:
         """
-        Make a request to the LLM API server
+        Make a request to the LLM API server with retry and exponential backoff.
+
+        Retries up to 3 times with exponential backoff (2s base delay) for
+        transient failures (5xx errors, connection errors, timeouts).
 
         Args:
             endpoint (str): API endpoint
@@ -37,45 +41,93 @@ class APIClient:
         Returns:
             dict: Response from the API
         """
-        try:
-            # Ensure base_url doesn't have trailing slash and endpoint has leading slash
-            base = self.base_url.rstrip("/")
-            endpoint = endpoint if endpoint.startswith("/") else f"/{endpoint}"
-            url = f"{base}{endpoint}"
+        max_retries = self.config.get("max_retries", 3)
+        base_delay = self.config.get("retry_base_delay", 2)
 
-            headers = {
-                "Content-Type": "application/json",
-                "User-Agent": "clover-cli/1.0",
-                "Accept": "application/json",
+        last_exception = None
+
+        for attempt in range(max_retries + 1):
+            try:
+                # Ensure base_url doesn't have trailing slash and endpoint has leading slash
+                base = self.base_url.rstrip("/")
+                endpoint = endpoint if endpoint.startswith("/") else f"/{endpoint}"
+                url = f"{base}{endpoint}"
+
+                headers = {
+                    "Content-Type": "application/json",
+                    "User-Agent": "clover-cli/1.0",
+                    "Accept": "application/json",
+                }
+
+                # Add API key if available
+                if self.api_key:
+                    headers["Authorization"] = f"Bearer {self.api_key}"
+
+                if method == "GET":
+                    response = requests.get(
+                        url,
+                        headers=headers,
+                        timeout=self.config.get("timeout", 300),
+                    )
+                elif method == "POST":
+                    response = requests.post(
+                        url,
+                        headers=headers,
+                        json=data,
+                        timeout=self.config.get("timeout", 300),
+                    )
+                else:
+                    raise ValueError(f"Unsupported HTTP method: {method}")
+
+                # Retry on 5xx server errors
+                if response.status_code >= 500 and attempt < max_retries:
+                    delay = base_delay * (2**attempt)
+                    print(
+                        f"Server error {response.status_code}, "
+                        f"retrying in {delay}s (attempt {attempt + 1}/{max_retries})"
+                    )
+                    time.sleep(delay)
+                    continue
+
+                response.raise_for_status()
+                return {"success": True, "data": response.json()}
+
+            except requests.exceptions.Timeout as e:
+                last_exception = e
+                if attempt < max_retries:
+                    delay = base_delay * (2**attempt)
+                    print(
+                        f"Timeout, retrying in {delay}s "
+                        f"(attempt {attempt + 1}/{max_retries})"
+                    )
+                    time.sleep(delay)
+                    continue
+
+            except requests.exceptions.ConnectionError as e:
+                last_exception = e
+                if attempt < max_retries:
+                    delay = base_delay * (2**attempt)
+                    print(
+                        f"Connection error, retrying in {delay}s "
+                        f"(attempt {attempt + 1}/{max_retries})"
+                    )
+                    time.sleep(delay)
+                    continue
+
+            except requests.exceptions.RequestException as e:
+                return {"success": False, "error": f"HTTP Request failed: {str(e)}"}
+            except json.JSONDecodeError as e:
+                return {"success": False, "error": f"Invalid JSON response: {str(e)}"}
+            except Exception as e:
+                return {"success": False, "error": f"Unexpected error: {str(e)}"}
+
+        # All retries exhausted
+        if last_exception:
+            return {
+                "success": False,
+                "error": f"Request failed after {max_retries} retries: {str(last_exception)}",
             }
-
-            # Add API key if available
-            if self.api_key:
-                headers["Authorization"] = f"Bearer {self.api_key}"
-
-            if method == "GET":
-                response = requests.get(
-                    url, headers=headers, timeout=self.config.get("timeout", 300)
-                )
-            elif method == "POST":
-                response = requests.post(
-                    url,
-                    headers=headers,
-                    json=data,
-                    timeout=self.config.get("timeout", 300),
-                )
-            else:
-                raise ValueError(f"Unsupported HTTP method: {method}")
-
-            response.raise_for_status()
-            return {"success": True, "data": response.json()}
-
-        except requests.exceptions.RequestException as e:
-            return {"success": False, "error": f"HTTP Request failed: {str(e)}"}
-        except json.JSONDecodeError as e:
-            return {"success": False, "error": f"Invalid JSON response: {str(e)}"}
-        except Exception as e:
-            return {"success": False, "error": f"Unexpected error: {str(e)}"}
+        return {"success": False, "error": "Request failed after maximum retries"}
 
     def list_models(self) -> Dict[str, Any]:
         """