diff --git a/devgen/providers/anthropic.py b/devgen/providers/anthropic.py
index f9174bb..1516398 100644
--- a/devgen/providers/anthropic.py
+++ b/devgen/providers/anthropic.py
@@ -1,5 +1,7 @@
 import anthropic
 
+from devgen.utils import format_token_limit_error, is_token_limit_error
+
 
 class AnthropicProvider:
     """Generates content using Anthropic's Claude models."""
@@ -23,4 +25,9 @@ class AnthropicProvider:
             )
             return message.content[0].text.strip()
         except Exception as e:
-            raise RuntimeError(f"Anthropic generation failed: {e}")
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("Anthropic", e)) from e
+            raise RuntimeError(
+                f"Anthropic generation failed: {e}. "
+                "Check the model id and your account credits."
+            ) from e
diff --git a/devgen/providers/gemini.py b/devgen/providers/gemini.py
index 8ceafc8..4b25feb 100644
--- a/devgen/providers/gemini.py
+++ b/devgen/providers/gemini.py
@@ -2,6 +2,8 @@ import time
 from google import genai
 from google.genai import types
 
+from devgen.utils import format_token_limit_error, is_token_limit_error
+
 
 class GeminiProvider:
     """Generates content using Google's Gemini models."""
@@ -40,6 +42,10 @@ class GeminiProvider:
                 return response.text.strip()
             except Exception as e:
                 error_msg = str(e).upper()
+                # Token / context-window overflow is not retryable — no point
+                # backing off, the prompt is just too big.
+                if is_token_limit_error(e):
+                    raise RuntimeError(format_token_limit_error("Gemini", e)) from e
                 # Check for 429 or ResourceExhausted in common error formats
                 if any(
                     x in error_msg
diff --git a/devgen/providers/huggingface.py b/devgen/providers/huggingface.py
index 221a34e..90dc4d2 100644
--- a/devgen/providers/huggingface.py
+++ b/devgen/providers/huggingface.py
@@ -1,5 +1,7 @@
 import requests
 
+from devgen.utils import format_token_limit_error, is_token_limit_error
+
 
 class HuggingfaceProvider:
     """Generates content using Hugging Face Inference API."""
@@ -46,6 +48,10 @@ class HuggingfaceProvider:
                         f"Hugging Face model is loading: {err}. "
                         "Wait a minute and retry, or pick a different model."
                     )
+                if is_token_limit_error(err):
+                    raise RuntimeError(
+                        format_token_limit_error("Hugging Face", err)
+                    ) from err
                 raise RuntimeError(f"Hugging Face API error: {err}")
             else:
                 raise RuntimeError(
@@ -55,6 +61,8 @@ class HuggingfaceProvider:
 
         except requests.HTTPError as e:
             status = e.response.status_code if e.response is not None else "?"
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("Hugging Face", e)) from e
             raise RuntimeError(
                 f"Hugging Face request failed (HTTP {status}): {e}. "
                 "Check the model id and your token permissions."
@@ -63,5 +71,9 @@ class HuggingfaceProvider:
             raise RuntimeError(
                 f"Hugging Face network error: {e}. Check your connection."
             ) from e
+        except RuntimeError:
+            raise
         except Exception as e:
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("Hugging Face", e)) from e
             raise RuntimeError(f"Hugging Face generation failed: {e}") from e
diff --git a/devgen/providers/ollama.py b/devgen/providers/ollama.py
index 2b362a4..577b07c 100644
--- a/devgen/providers/ollama.py
+++ b/devgen/providers/ollama.py
@@ -1,3 +1,4 @@
+from devgen.utils import format_token_limit_error, is_token_limit_error
 
 
 class OllamaProvider:
@@ -37,6 +38,8 @@ class OllamaProvider:
                 **kwargs,
             )
         except Exception as e:
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("Ollama", e)) from e
             raise RuntimeError(
                 f"Ollama request failed (host={host}, model={chosen_model}): {e}. "
                 "Is the Ollama server running? Start it with `ollama serve` and "
diff --git a/devgen/providers/openai.py b/devgen/providers/openai.py
index d3cd3ff..4bf155d 100644
--- a/devgen/providers/openai.py
+++ b/devgen/providers/openai.py
@@ -1,5 +1,7 @@
 from openai import OpenAI
 
+from devgen.utils import format_token_limit_error, is_token_limit_error
+
 
 class OpenaiProvider:
     """Generates a response string using the OpenAI ChatCompletion API based on the provided prompt and parameters. This method initializes an OpenAI client with the given API key, sends a chat completion request with specified model and additional parameters, and returns the content of the generated message.
@@ -59,6 +61,8 @@ class OpenaiProvider:
                 **kwargs,
             )
         except Exception as e:
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("OpenAI", e)) from e
             raise RuntimeError(
                 f"OpenAI request failed: {e}. "
                 "Check the model name, API key permissions, and your account quota."
diff --git a/devgen/providers/openrouter.py b/devgen/providers/openrouter.py
index 5b9355c..3eea592 100644
--- a/devgen/providers/openrouter.py
+++ b/devgen/providers/openrouter.py
@@ -1,5 +1,7 @@
 from openai import OpenAI
 
+from devgen.utils import format_token_limit_error, is_token_limit_error
+
 
 class OpenrouterProvider:
     """Generates content using OpenRouter (OpenAI-compatible API)."""
@@ -36,6 +38,8 @@ class OpenrouterProvider:
             )
             return response.choices[0].message.content.strip()
         except Exception as e:
+            if is_token_limit_error(e):
+                raise RuntimeError(format_token_limit_error("OpenRouter", e)) from e
             raise RuntimeError(
                 f"OpenRouter request failed: {e}. "
                 "Verify the model id (e.g. `openai/gpt-4o`) and your API key credits."