diff --git a/README.md b/README.md
index 2ef1b2b..9eabf7a 100644
--- a/README.md
+++ b/README.md
@@ -41,7 +41,7 @@ Nerve features integrations for any model accessible via the following providers
 | **Mistral.ai** | `MISTRAL_API_KEY` | `mistral://mistral-large-latest` |
 | **Novita** | `NOVITA_API_KEY` | `novita://meta-llama/llama-3.1-70b-instruct` |
 
-¹ **o1-preview and o1 models do not support function calling directly** and do not support a system prompt. It is possible to workaround this by adding the `--user-only` flag to the command line.
+¹ **o1-preview and o1 models do not support function calling directly** and do not support a system prompt. Nerve will try to detect this and fallback to user prompt. It is possible to force this behaviour by adding the `--user-only` flag to the command line.
 
 ² Refer to [this document](https://huggingface.co/blog/tgi-messages-api#using-inference-endpoints-with-openai-client-libraries) for how to configure a custom Huggingface endpoint.
 
diff --git a/src/agent/generator/anthropic.rs b/src/agent/generator/anthropic.rs
index 2a748e1..2b2c1a4 100644
--- a/src/agent/generator/anthropic.rs
+++ b/src/agent/generator/anthropic.rs
@@ -1,7 +1,7 @@
 use std::collections::HashMap;
 
 use crate::agent::{
-    generator::{ChatResponse, Usage},
+    generator::{ChatResponse, SupportedFeatures, Usage},
     state::SharedState,
     Invocation,
 };
@@ -102,7 +102,7 @@ impl Client for AnthropicClient {
         Ok(Self { model, client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
         let messages = vec![Message::user("Execute the test function.")];
         let max_tokens = MaxTokens::new(4096, self.model)?;
 
@@ -128,9 +128,15 @@ impl Client for AnthropicClient {
         log::debug!("response = {:?}", response);
 
         if let Ok(tool_use) = response.content.flatten_into_tool_use() {
-            Ok(tool_use.name == "test")
+            Ok(SupportedFeatures {
+                system_prompt: true,
+                tools: tool_use.name == "test",
+            })
         } else {
-            Ok(false)
+            Ok(SupportedFeatures {
+                system_prompt: true,
+                tools: false,
+            })
         }
     }
 
@@ -183,10 +189,10 @@ impl Client for AnthropicClient {
 
         let request_body = MessagesRequestBody {
             model: self.model,
-            system: match &options.system_prompt {
-                Some(sp) => Some(SystemPrompt::new(sp.trim())),
-                None => None,
-            },
+            system: options
+                .system_prompt
+                .as_ref()
+                .map(|sp| SystemPrompt::new(sp.trim())),
             messages,
             max_tokens,
             tools: if tools.is_empty() { None } else { Some(tools) },
diff --git a/src/agent/generator/deepseek.rs b/src/agent/generator/deepseek.rs
index c07f44c..bf24c97 100644
--- a/src/agent/generator/deepseek.rs
+++ b/src/agent/generator/deepseek.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct DeepSeekClient {
     client: OpenAIClient,
@@ -24,8 +24,8 @@ impl Client for DeepSeekClient {
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
diff --git a/src/agent/generator/fireworks.rs b/src/agent/generator/fireworks.rs
index ce626f9..6dc8ae8 100644
--- a/src/agent/generator/fireworks.rs
+++ b/src/agent/generator/fireworks.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct FireworksClient {
     client: OpenAIClient,
@@ -24,6 +24,10 @@ impl Client for FireworksClient {
         Ok(Self { client })
     }
 
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
+    }
+
     async fn chat(
         &self,
         state: SharedState,
diff --git a/src/agent/generator/groq.rs b/src/agent/generator/groq.rs
index c3cfe39..095f817 100644
--- a/src/agent/generator/groq.rs
+++ b/src/agent/generator/groq.rs
@@ -17,7 +17,7 @@ use crate::agent::{
     Invocation,
 };
 
-use super::{ChatOptions, Client};
+use super::{ChatOptions, Client, SupportedFeatures};
 
 lazy_static! {
     static ref RETRY_TIME_PARSER: Regex =
@@ -58,7 +58,7 @@ impl Client for GroqClient {
         Ok(Self { model, api_key })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
         let chat_history = vec![
             crate::api::groq::completion::message::Message::SystemMessage {
                 role: Some("system".to_string()),
@@ -106,7 +106,10 @@ impl Client for GroqClient {
 
         log::debug!("groq.check_tools_support.resp = {:?}", &resp);
 
-        Ok(resp.is_ok())
+        Ok(SupportedFeatures {
+            system_prompt: true,
+            tools: resp.is_ok(),
+        })
     }
 
     async fn chat(
diff --git a/src/agent/generator/huggingface.rs b/src/agent/generator/huggingface.rs
index 6b83c2a..71b8325 100644
--- a/src/agent/generator/huggingface.rs
+++ b/src/agent/generator/huggingface.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct HuggingfaceMessageClient {
     client: OpenAIClient,
@@ -23,8 +23,8 @@ impl Client for HuggingfaceMessageClient {
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
diff --git a/src/agent/generator/mistral.rs b/src/agent/generator/mistral.rs
index be0b79f..e9751e2 100644
--- a/src/agent/generator/mistral.rs
+++ b/src/agent/generator/mistral.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct MistralClient {
     client: OpenAIClient,
@@ -15,13 +15,14 @@ impl Client for MistralClient {
     where
         Self: Sized,
     {
-        let client = OpenAIClient::custom(model_name, "MISTRAL_API_KEY", "https://api.mistral.ai/v1/")?;
+        let client =
+            OpenAIClient::custom(model_name, "MISTRAL_API_KEY", "https://api.mistral.ai/v1/")?;
 
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
@@ -33,7 +34,7 @@ impl Client for MistralClient {
 
         if let Err(error) = &response {
             if self.check_rate_limit(&error.to_string()).await {
-                return self.chat(state, options).await;                
+                return self.chat(state, options).await;
             }
         }
 
diff --git a/src/agent/generator/mod.rs b/src/agent/generator/mod.rs
index 325cc54..cda89ee 100644
--- a/src/agent/generator/mod.rs
+++ b/src/agent/generator/mod.rs
@@ -89,6 +89,20 @@ pub struct ChatResponse {
     pub usage: Option<Usage>,
 }
 
+pub struct SupportedFeatures {
+    pub system_prompt: bool,
+    pub tools: bool,
+}
+
+impl Default for SupportedFeatures {
+    fn default() -> Self {
+        Self {
+            system_prompt: true,
+            tools: false,
+        }
+    }
+}
+
 #[async_trait]
 pub trait Client: mini_rag::Embedder + Send + Sync {
     fn new(url: &str, port: u16, model_name: &str, context_window: u32) -> Result<Self>
@@ -97,8 +111,8 @@ pub trait Client: mini_rag::Embedder + Send + Sync {
 
     async fn chat(&self, state: SharedState, options: &ChatOptions) -> Result<ChatResponse>;
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        Ok(false)
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        Ok(SupportedFeatures::default())
     }
 
     async fn check_rate_limit(&self, error: &str) -> bool {
diff --git a/src/agent/generator/nim.rs b/src/agent/generator/nim.rs
index ebeca45..43b2431 100644
--- a/src/agent/generator/nim.rs
+++ b/src/agent/generator/nim.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct NvidiaNIMClient {
     client: OpenAIClient,
@@ -30,8 +30,8 @@ impl Client for NvidiaNIMClient {
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
diff --git a/src/agent/generator/novita.rs b/src/agent/generator/novita.rs
index 7dd8574..5ebf4a1 100644
--- a/src/agent/generator/novita.rs
+++ b/src/agent/generator/novita.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct NovitaClient {
     client: OpenAIClient,
@@ -24,6 +24,10 @@ impl Client for NovitaClient {
         Ok(Self { client })
     }
 
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
+    }
+
     async fn chat(
         &self,
         state: SharedState,
diff --git a/src/agent/generator/ollama.rs b/src/agent/generator/ollama.rs
index 479b53d..1a25b02 100644
--- a/src/agent/generator/ollama.rs
+++ b/src/agent/generator/ollama.rs
@@ -18,7 +18,7 @@ use async_trait::async_trait;
 
 use crate::agent::{state::SharedState, Invocation};
 
-use super::{ChatOptions, ChatResponse, Client, Message};
+use super::{ChatOptions, ChatResponse, Client, Message, SupportedFeatures};
 
 pub struct OllamaClient {
     model: String,
@@ -51,7 +51,7 @@ impl Client for OllamaClient {
         })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
         let chat_history = vec![
             ChatMessage::system("You are an helpful assistant.".to_string()),
             ChatMessage::user("Call the test function.".to_string()),
@@ -79,12 +79,18 @@ impl Client for OllamaClient {
 
         if let Err(err) = self.client.send_chat_messages(request).await {
             if err.to_string().contains("does not support tools") {
-                Ok(false)
+                Ok(SupportedFeatures {
+                    system_prompt: true,
+                    tools: false,
+                })
             } else {
                 Err(anyhow!(err))
             }
         } else {
-            Ok(true)
+            Ok(SupportedFeatures {
+                system_prompt: true,
+                tools: true,
+            })
         }
     }
 
diff --git a/src/agent/generator/openai.rs b/src/agent/generator/openai.rs
index 453e614..4b4f73b 100644
--- a/src/agent/generator/openai.rs
+++ b/src/agent/generator/openai.rs
@@ -9,7 +9,7 @@ use serde::{Deserialize, Serialize};
 
 use crate::agent::{state::SharedState, Invocation};
 
-use super::{ChatOptions, ChatResponse, Client, Message};
+use super::{ChatOptions, ChatResponse, Client, Message, SupportedFeatures};
 
 #[derive(Debug, Clone, Serialize, Deserialize)]
 pub struct OpenAiToolFunctionParameterProperty {
@@ -130,7 +130,7 @@ impl Client for OpenAIClient {
         Self::custom(model_name, "OPENAI_API_KEY", "https://api.openai.com/v1/")
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
         let chat_history = vec![
             crate::api::openai::Message {
                 role: Role::System,
@@ -172,18 +172,35 @@ impl Client for OpenAIClient {
 
         log::debug!("openai.check_tools_support.resp = {:?}", &resp);
 
+        let mut system_prompt_support = true;
+
         if let Ok(comp) = resp {
             if !comp.choices.is_empty() {
                 let first = comp.choices.first().unwrap();
                 if let Some(m) = first.message.as_ref() {
                     if m.tool_calls.is_some() {
-                        return Ok(true);
+                        return Ok(SupportedFeatures {
+                            system_prompt: true,
+                            tools: true,
+                        });
                     }
                 }
             }
+        } else {
+            let api_error = resp.unwrap_err().to_string();
+            if api_error.contains("unsupported_value")
+                && api_error.contains("does not support 'system' with this model")
+            {
+                system_prompt_support = false;
+            } else {
+                log::error!("openai.check_tools_support.error = {}", api_error);
+            }
         }
 
-        Ok(false)
+        Ok(SupportedFeatures {
+            system_prompt: system_prompt_support,
+            tools: false,
+        })
     }
 
     async fn chat(
diff --git a/src/agent/generator/openai_compatible.rs b/src/agent/generator/openai_compatible.rs
index 1588fd1..31e537b 100644
--- a/src/agent/generator/openai_compatible.rs
+++ b/src/agent/generator/openai_compatible.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct OpenAiCompatibleClient {
     client: OpenAIClient,
@@ -30,8 +30,8 @@ impl Client for OpenAiCompatibleClient {
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
diff --git a/src/agent/generator/xai.rs b/src/agent/generator/xai.rs
index ce9dff7..6f9285a 100644
--- a/src/agent/generator/xai.rs
+++ b/src/agent/generator/xai.rs
@@ -3,7 +3,7 @@ use async_trait::async_trait;
 
 use crate::agent::state::SharedState;
 
-use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client};
+use super::{openai::OpenAIClient, ChatOptions, ChatResponse, Client, SupportedFeatures};
 
 pub struct XAIClient {
     client: OpenAIClient,
@@ -20,8 +20,8 @@ impl Client for XAIClient {
         Ok(Self { client })
     }
 
-    async fn check_native_tools_support(&self) -> Result<bool> {
-        self.client.check_native_tools_support().await
+    async fn check_supported_features(&self) -> Result<SupportedFeatures> {
+        self.client.check_supported_features().await
     }
 
     async fn chat(
diff --git a/src/agent/mod.rs b/src/agent/mod.rs
index f7aca43..25fcbc1 100644
--- a/src/agent/mod.rs
+++ b/src/agent/mod.rs
@@ -123,12 +123,14 @@ impl Agent {
         user_only: bool,
         max_iterations: usize,
     ) -> Result<Self> {
+        // check if the model supports tools calling and system prompt natively
+        let supported_features = generator.check_supported_features().await?;
+
         let use_native_tools_format = if force_strategy {
             log::info!("using {:?} serialization strategy", &serializer);
             false
         } else {
-            // check if the model supports tools calling natively
-            match generator.check_native_tools_support().await? {
+            match supported_features.tools {
                 true => {
                     log::debug!("model supports tools calling natively.");
                     true
@@ -140,6 +142,14 @@ impl Agent {
             }
         };
 
+        let user_only = if !user_only && !supported_features.system_prompt {
+            log::info!("model does not support system prompt, forcing user prompt");
+            true
+        } else {
+            // leave whatever the user set
+            user_only
+        };
+
         let task_timeout = task.get_timeout();
         let state = Arc::new(tokio::sync::Mutex::new(
             State::new(