diff --git a/crates/brightstaff/src/handlers/agent_chat_completions.rs b/crates/brightstaff/src/handlers/agent_chat_completions.rs
index bac9607b..5ced34c0 100644
--- a/crates/brightstaff/src/handlers/agent_chat_completions.rs
+++ b/crates/brightstaff/src/handlers/agent_chat_completions.rs
@@ -402,7 +402,7 @@ async fn handle_agent_chat(
         // and add it to the conversation history
         current_messages.push(OpenAIMessage {
             role: hermesllm::apis::openai::Role::Assistant,
-            content: hermesllm::apis::openai::MessageContent::Text(response_text),
+            content: Some(hermesllm::apis::openai::MessageContent::Text(response_text)),
             name: Some(agent_name.clone()),
             tool_calls: None,
             tool_call_id: None,
diff --git a/crates/brightstaff/src/handlers/function_calling.rs b/crates/brightstaff/src/handlers/function_calling.rs
index 8f641df6..7ba15e2d 100644
--- a/crates/brightstaff/src/handlers/function_calling.rs
+++ b/crates/brightstaff/src/handlers/function_calling.rs
@@ -638,7 +638,7 @@ impl ArchFunctionHandler {
             let system_prompt = self.format_system_prompt(tools)?;
             processed_messages.push(Message {
                 role: Role::System,
-                content: MessageContent::Text(system_prompt),
+                content: Some(MessageContent::Text(system_prompt)),
                 name: None,
                 tool_calls: None,
                 tool_call_id: None,
@@ -649,8 +649,9 @@ impl ArchFunctionHandler {
         for (idx, message) in messages.iter().enumerate() {
             let mut role = message.role.clone();
             let mut content = match &message.content {
-                MessageContent::Text(text) => text.clone(),
-                MessageContent::Parts(_) => String::new(),
+                Some(MessageContent::Text(text)) => text.clone(),
+                Some(MessageContent::Parts(_)) => String::new(),
+                None => String::new(),
             };
 
             // Handle tool calls
@@ -675,7 +676,8 @@ impl ArchFunctionHandler {
                 } else {
                     // Get the tool call from previous message
                     if idx > 0 {
-                        if let MessageContent::Text(prev_content) = &messages[idx - 1].content {
+                        if let Some(MessageContent::Text(prev_content)) = &messages[idx - 1].content
+                        {
                             let mut tool_call_msg = prev_content.clone();
 
                             // Strip markdown code blocks
@@ -721,7 +723,7 @@ impl ArchFunctionHandler {
 
             processed_messages.push(Message {
                 role,
-                content: MessageContent::Text(content),
+                content: Some(MessageContent::Text(content)),
                 name: message.name.clone(),
                 tool_calls: None,
                 tool_call_id: None,
@@ -740,7 +742,7 @@ impl ArchFunctionHandler {
         // Add extra instruction if provided
         if let Some(instruction) = extra_instruction {
             if let Some(last) = processed_messages.last_mut() {
-                if let MessageContent::Text(content) = &mut last.content {
+                if let Some(MessageContent::Text(content)) = &mut last.content {
                     content.push('\n');
                     content.push_str(instruction);
                 }
@@ -761,7 +763,7 @@ impl ArchFunctionHandler {
         // Keep system message if present
         if let Some(first) = messages.first() {
             if first.role == Role::System {
-                if let MessageContent::Text(content) = &first.content {
+                if let Some(MessageContent::Text(content)) = &first.content {
                     num_tokens += content.len() / 4; // Approximate 4 chars per token
                 }
                 conversation_idx = 1;
@@ -772,7 +774,7 @@ impl ArchFunctionHandler {
         // Start with message_idx pointing past the end (will be used if no truncation needed)
         let mut message_idx = messages.len();
         for i in (conversation_idx..messages.len()).rev() {
-            if let MessageContent::Text(content) = &messages[i].content {
+            if let Some(MessageContent::Text(content)) = &messages[i].content {
                 num_tokens += content.len() / 4;
                 if num_tokens >= max_tokens && messages[i].role == Role::User {
                     // Set message_idx to current position and break
@@ -802,7 +804,7 @@ impl ArchFunctionHandler {
     pub fn prefill_message(&self, mut messages: Vec<Message>, prefill: &str) -> Vec<Message> {
         messages.push(Message {
             role: Role::Assistant,
-            content: MessageContent::Text(prefill.to_string()),
+            content: Some(MessageContent::Text(prefill.to_string())),
             name: None,
             tool_calls: None,
             tool_call_id: None,
diff --git a/crates/brightstaff/src/handlers/integration_tests.rs b/crates/brightstaff/src/handlers/integration_tests.rs
index 29552f83..9239f94a 100644
--- a/crates/brightstaff/src/handlers/integration_tests.rs
+++ b/crates/brightstaff/src/handlers/integration_tests.rs
@@ -28,7 +28,7 @@ mod tests {
     fn create_test_message(role: Role, content: &str) -> Message {
         Message {
             role,
-            content: MessageContent::Text(content.to_string()),
+            content: Some(MessageContent::Text(content.to_string())),
             name: None,
             tool_calls: None,
             tool_call_id: None,
@@ -129,7 +129,7 @@ mod tests {
         let processed_messages = result.unwrap();
         // With empty filter chain, should return the original messages unchanged
         assert_eq!(processed_messages.len(), 1);
-        if let MessageContent::Text(content) = &processed_messages[0].content {
+        if let Some(MessageContent::Text(content)) = &processed_messages[0].content {
             assert_eq!(content, "Hello world!");
         } else {
             panic!("Expected text content");
diff --git a/crates/brightstaff/src/handlers/pipeline_processor.rs b/crates/brightstaff/src/handlers/pipeline_processor.rs
index 09520617..bc36de01 100644
--- a/crates/brightstaff/src/handlers/pipeline_processor.rs
+++ b/crates/brightstaff/src/handlers/pipeline_processor.rs
@@ -887,7 +887,7 @@ mod tests {
     fn create_test_message(role: Role, content: &str) -> Message {
         Message {
             role,
-            content: MessageContent::Text(content.to_string()),
+            content: Some(MessageContent::Text(content.to_string())),
             name: None,
             tool_calls: None,
             tool_call_id: None,
diff --git a/crates/brightstaff/src/handlers/router_chat.rs b/crates/brightstaff/src/handlers/router_chat.rs
index 67e25338..701e8e51 100644
--- a/crates/brightstaff/src/handlers/router_chat.rs
+++ b/crates/brightstaff/src/handlers/router_chat.rs
@@ -95,7 +95,9 @@ pub async fn router_chat_get_upstream_model(
         .messages
         .last()
         .map_or("None".to_string(), |msg| {
-            msg.content.to_string().replace('\n', "\\n")
+            msg.content
+                .as_ref()
+                .map_or("None".to_string(), |c| c.to_string().replace('\n', "\\n"))
         });
 
     const MAX_MESSAGE_LENGTH: usize = 50;
diff --git a/crates/brightstaff/src/router/orchestrator_model_v1.rs b/crates/brightstaff/src/router/orchestrator_model_v1.rs
index ef32db83..8d64f8e7 100644
--- a/crates/brightstaff/src/router/orchestrator_model_v1.rs
+++ b/crates/brightstaff/src/router/orchestrator_model_v1.rs
@@ -2,6 +2,7 @@ use std::collections::HashMap;
 
 use common::configuration::{AgentUsagePreference, OrchestrationPreference};
 use hermesllm::apis::openai::{ChatCompletionsRequest, Message, MessageContent, Role};
+use hermesllm::transforms::lib::ExtractText;
 use serde::{ser::Serialize as SerializeTrait, Deserialize, Serialize};
 use tracing::{debug, warn};
 
@@ -181,7 +182,9 @@ impl OrchestratorModel for OrchestratorModelV1 {
         let messages_vec = messages
             .iter()
             .filter(|m| {
-                m.role != Role::System && m.role != Role::Tool && !m.content.to_string().is_empty()
+                m.role != Role::System
+                    && m.role != Role::Tool
+                    && !m.content.extract_text().is_empty()
             })
             .collect::<Vec<&Message>>();
 
@@ -190,7 +193,7 @@ impl OrchestratorModel for OrchestratorModelV1 {
         let mut token_count = ARCH_ORCHESTRATOR_V1_SYSTEM_PROMPT.len() / TOKEN_LENGTH_DIVISOR;
         let mut selected_messages_list_reversed: Vec<&Message> = vec![];
         for (selected_messsage_count, message) in messages_vec.iter().rev().enumerate() {
-            let message_token_count = message.content.to_string().len() / TOKEN_LENGTH_DIVISOR;
+            let message_token_count = message.content.extract_text().len() / TOKEN_LENGTH_DIVISOR;
             token_count += message_token_count;
             if token_count > self.max_token_length {
                 debug!(
@@ -240,7 +243,12 @@ impl OrchestratorModel for OrchestratorModelV1 {
             .rev()
             .map(|message| Message {
                 role: message.role.clone(),
-                content: MessageContent::Text(message.content.to_string()),
+                content: Some(MessageContent::Text(
+                    message
+                        .content
+                        .as_ref()
+                        .map_or(String::new(), |c| c.to_string()),
+                )),
                 name: None,
                 tool_calls: None,
                 tool_call_id: None,
@@ -262,7 +270,7 @@ impl OrchestratorModel for OrchestratorModelV1 {
         ChatCompletionsRequest {
             model: self.orchestration_model.clone(),
             messages: vec![Message {
-                content: MessageContent::Text(orchestrator_message),
+                content: Some(MessageContent::Text(orchestrator_message)),
                 role: Role::User,
                 name: None,
                 tool_calls: None,
@@ -539,7 +547,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -618,7 +626,7 @@ If no routes are needed, return an empty list for `route`.
         }]);
         let req = orchestrator.generate_request(&conversation, &usage_preferences);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -689,7 +697,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -761,7 +769,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -848,7 +856,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -940,7 +948,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -1058,7 +1066,7 @@ If no routes are needed, return an empty list for `route`.
 
         let req: ChatCompletionsRequest = orchestrator.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
diff --git a/crates/brightstaff/src/router/router_model_v1.rs b/crates/brightstaff/src/router/router_model_v1.rs
index 84680928..796dfaac 100644
--- a/crates/brightstaff/src/router/router_model_v1.rs
+++ b/crates/brightstaff/src/router/router_model_v1.rs
@@ -2,6 +2,7 @@ use std::collections::HashMap;
 
 use common::configuration::{ModelUsagePreference, RoutingPreference};
 use hermesllm::apis::openai::{ChatCompletionsRequest, Message, MessageContent, Role};
+use hermesllm::transforms::lib::ExtractText;
 use serde::{Deserialize, Serialize};
 use tracing::{debug, warn};
 
@@ -78,7 +79,9 @@ impl RouterModel for RouterModelV1 {
         let messages_vec = messages
             .iter()
             .filter(|m| {
-                m.role != Role::System && m.role != Role::Tool && !m.content.to_string().is_empty()
+                m.role != Role::System
+                    && m.role != Role::Tool
+                    && !m.content.extract_text().is_empty()
             })
             .collect::<Vec<&Message>>();
 
@@ -87,7 +90,7 @@ impl RouterModel for RouterModelV1 {
         let mut token_count = ARCH_ROUTER_V1_SYSTEM_PROMPT.len() / TOKEN_LENGTH_DIVISOR;
         let mut selected_messages_list_reversed: Vec<&Message> = vec![];
         for (selected_messsage_count, message) in messages_vec.iter().rev().enumerate() {
-            let message_token_count = message.content.to_string().len() / TOKEN_LENGTH_DIVISOR;
+            let message_token_count = message.content.extract_text().len() / TOKEN_LENGTH_DIVISOR;
             token_count += message_token_count;
             if token_count > self.max_token_length {
                 debug!(
@@ -136,7 +139,12 @@ impl RouterModel for RouterModelV1 {
                 Message {
                     role: message.role.clone(),
                     // we can unwrap here because we have already filtered out messages without content
-                    content: MessageContent::Text(message.content.to_string()),
+                    content: Some(MessageContent::Text(
+                        message
+                            .content
+                            .as_ref()
+                            .map_or(String::new(), |c| c.to_string()),
+                    )),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
@@ -154,7 +162,7 @@ impl RouterModel for RouterModelV1 {
         ChatCompletionsRequest {
             model: self.routing_model.clone(),
             messages: vec![Message {
-                content: MessageContent::Text(router_message),
+                content: Some(MessageContent::Text(router_message)),
                 role: Role::User,
                 name: None,
                 tool_calls: None,
@@ -344,7 +352,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -409,7 +417,7 @@ Based on your analysis, provide your response in the following JSON formats if y
         }]);
         let req = router.generate_request(&conversation, &usage_preferences);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -469,7 +477,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -530,7 +538,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -598,7 +606,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -667,7 +675,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
@@ -762,7 +770,7 @@ Based on your analysis, provide your response in the following JSON formats if y
 
         let req: ChatCompletionsRequest = router.generate_request(&conversation, &None);
 
-        let prompt = req.messages[0].content.to_string();
+        let prompt = req.messages[0].content.extract_text();
 
         assert_eq!(expected_prompt, prompt);
     }
diff --git a/crates/brightstaff/src/signals/analyzer.rs b/crates/brightstaff/src/signals/analyzer.rs
index 9880bf2c..5ee3c7d9 100644
--- a/crates/brightstaff/src/signals/analyzer.rs
+++ b/crates/brightstaff/src/signals/analyzer.rs
@@ -1122,9 +1122,9 @@ pub struct TextBasedSignalAnalyzer {
 
 impl TextBasedSignalAnalyzer {
     /// Extract text content from MessageContent, skipping non-text content
-    fn extract_text(content: &hermesllm::apis::openai::MessageContent) -> Option<String> {
+    fn extract_text(content: &Option<hermesllm::apis::openai::MessageContent>) -> Option<String> {
         match content {
-            hermesllm::apis::openai::MessageContent::Text(text) => Some(text.clone()),
+            Some(hermesllm::apis::openai::MessageContent::Text(text)) => Some(text.clone()),
             // Tool calls and other structured content are skipped
             _ => None,
         }
@@ -1941,12 +1941,13 @@ impl Default for TextBasedSignalAnalyzer {
 mod tests {
     use super::*;
     use hermesllm::apis::openai::MessageContent;
+    use hermesllm::transforms::lib::ExtractText;
     use std::time::Instant;
 
     fn create_message(role: Role, content: &str) -> Message {
         Message {
             role,
-            content: MessageContent::Text(content.to_string()),
+            content: Some(MessageContent::Text(content.to_string())),
             name: None,
             tool_calls: None,
             tool_call_id: None,
@@ -2130,7 +2131,7 @@ mod tests {
             .iter()
             .enumerate()
             .map(|(i, msg)| {
-                let text = msg.content.to_string();
+                let text = msg.content.extract_text();
                 (i, msg.role.clone(), NormalizedMessage::from_text(&text))
             })
             .collect()
@@ -2532,7 +2533,7 @@ mod tests {
             |content: &str, tool_id: &str, tool_name: &str, args: &str| -> Message {
                 Message {
                     role: Role::Assistant,
-                    content: MessageContent::Text(content.to_string()),
+                    content: Some(MessageContent::Text(content.to_string())),
                     name: None,
                     tool_calls: Some(vec![ToolCall {
                         id: tool_id.to_string(),
@@ -2550,7 +2551,7 @@ mod tests {
         let create_tool_message = |tool_call_id: &str, content: &str| -> Message {
             Message {
                 role: Role::Tool,
-                content: MessageContent::Text(content.to_string()),
+                content: Some(MessageContent::Text(content.to_string())),
                 name: None,
                 tool_calls: None,
                 tool_call_id: Some(tool_call_id.to_string()),
@@ -2665,7 +2666,7 @@ mod tests {
             |content: &str, tool_id: &str, tool_name: &str, args: &str| -> Message {
                 Message {
                     role: Role::Assistant,
-                    content: MessageContent::Text(content.to_string()),
+                    content: Some(MessageContent::Text(content.to_string())),
                     name: None,
                     tool_calls: Some(vec![ToolCall {
                         id: tool_id.to_string(),
@@ -2683,7 +2684,7 @@ mod tests {
         let create_tool_message = |tool_call_id: &str, content: &str| -> Message {
             Message {
                 role: Role::Tool,
-                content: MessageContent::Text(content.to_string()),
+                content: Some(MessageContent::Text(content.to_string())),
                 name: None,
                 tool_calls: None,
                 tool_call_id: Some(tool_call_id.to_string()),
diff --git a/crates/hermesllm/src/apis/amazon_bedrock.rs b/crates/hermesllm/src/apis/amazon_bedrock.rs
index dbada283..e2cbc201 100644
--- a/crates/hermesllm/src/apis/amazon_bedrock.rs
+++ b/crates/hermesllm/src/apis/amazon_bedrock.rs
@@ -225,7 +225,7 @@ impl ProviderRequest for ConverseRequest {
                 if let SystemContentBlock::Text { text } = sys_block {
                     openai_messages.push(Message {
                         role: Role::System,
-                        content: MessageContent::Text(text.clone()),
+                        content: Some(MessageContent::Text(text.clone())),
                         name: None,
                         tool_calls: None,
                         tool_call_id: None,
@@ -258,7 +258,7 @@ impl ProviderRequest for ConverseRequest {
 
                 openai_messages.push(Message {
                     role,
-                    content: MessageContent::Text(content),
+                    content: Some(MessageContent::Text(content)),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
@@ -279,7 +279,7 @@ impl ProviderRequest for ConverseRequest {
         for msg in messages {
             match msg.role {
                 crate::apis::openai::Role::System => {
-                    if let crate::apis::openai::MessageContent::Text(text) = &msg.content {
+                    if let Some(crate::apis::openai::MessageContent::Text(text)) = &msg.content {
                         system_blocks.push(SystemContentBlock::Text { text: text.clone() });
                     }
                 }
@@ -290,12 +290,13 @@ impl ProviderRequest for ConverseRequest {
                         _ => continue,
                     };
 
-                    let content =
-                        if let crate::apis::openai::MessageContent::Text(text) = &msg.content {
-                            vec![ContentBlock::Text { text: text.clone() }]
-                        } else {
-                            vec![]
-                        };
+                    let content = if let Some(crate::apis::openai::MessageContent::Text(text)) =
+                        &msg.content
+                    {
+                        vec![ContentBlock::Text { text: text.clone() }]
+                    } else {
+                        vec![]
+                    };
 
                     bedrock_messages.push(crate::apis::amazon_bedrock::Message { role, content });
                 }
diff --git a/crates/hermesllm/src/apis/anthropic.rs b/crates/hermesllm/src/apis/anthropic.rs
index ed3317ce..6e53e6db 100644
--- a/crates/hermesllm/src/apis/anthropic.rs
+++ b/crates/hermesllm/src/apis/anthropic.rs
@@ -584,7 +584,7 @@ impl ProviderRequest for MessagesRequest {
             let system_text = system_messages
                 .iter()
                 .filter_map(|msg| {
-                    if let crate::apis::openai::MessageContent::Text(text) = &msg.content {
+                    if let Some(crate::apis::openai::MessageContent::Text(text)) = &msg.content {
                         Some(text.as_str())
                     } else {
                         None
diff --git a/crates/hermesllm/src/apis/openai.rs b/crates/hermesllm/src/apis/openai.rs
index 834c33ec..cd4e7d0b 100644
--- a/crates/hermesllm/src/apis/openai.rs
+++ b/crates/hermesllm/src/apis/openai.rs
@@ -155,7 +155,8 @@ pub enum Role {
 #[derive(Serialize, Deserialize, Debug, Clone)]
 pub struct Message {
     pub role: Role,
-    pub content: MessageContent,
+    /// The contents of the message. Required unless tool_calls is specified (for assistant role)
+    pub content: Option<MessageContent>,
     pub name: Option<String>,
     /// Tool calls made by the assistant (only present for assistant role)
     pub tool_calls: Option<Vec<ToolCall>>,
@@ -204,8 +205,7 @@ impl ResponseMessage {
             content: self
                 .content
                 .as_ref()
-                .map(|s| MessageContent::Text(s.clone()))
-                .unwrap_or(MessageContent::Text(String::new())),
+                .map(|s| MessageContent::Text(s.clone())),
             name: None, // Response messages don't have names in the same way request messages do
             tool_calls: self.tool_calls.clone(),
             tool_call_id: None, // Response messages don't have tool_call_id
@@ -233,6 +233,12 @@ impl ExtractText for MessageContent {
     }
 }
 
+impl ExtractText for Option<MessageContent> {
+    fn extract_text(&self) -> String {
+        self.as_ref().map(|c| c.extract_text()).unwrap_or_default()
+    }
+}
+
 impl ExtractText for Vec<ContentPart> {
     fn extract_text(&self) -> String {
         self.iter()
@@ -247,23 +253,7 @@ impl ExtractText for Vec<ContentPart> {
 
 impl Display for MessageContent {
     fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        match self {
-            MessageContent::Text(text) => write!(f, "{}", text),
-            MessageContent::Parts(parts) => {
-                let text_parts: Vec<String> = parts
-                    .iter()
-                    .filter_map(|part| match part {
-                        ContentPart::Text { text } => Some(text.clone()),
-                        ContentPart::ImageUrl { .. } => {
-                            // skip image URLs or their data in text representation
-                            None
-                        }
-                    })
-                    .collect();
-                let combined_text = text_parts.join("\n");
-                write!(f, "{}", combined_text)
-            }
-        }
+        write!(f, "{}", self.extract_text())
     }
 }
 
@@ -622,8 +612,10 @@ impl ProviderRequest for ChatCompletionsRequest {
 
     fn extract_messages_text(&self) -> String {
         self.messages.iter().fold(String::new(), |acc, m| {
-            acc + " "
-                + &match &m.content {
+            let content_text = m
+                .content
+                .as_ref()
+                .map(|content| match content {
                     MessageContent::Text(text) => text.clone(),
                     MessageContent::Parts(parts) => parts
                         .iter()
@@ -633,16 +625,18 @@ impl ProviderRequest for ChatCompletionsRequest {
                         })
                         .collect::<Vec<_>>()
                         .join(" "),
-                }
+                })
+                .unwrap_or_default();
+            acc + " " + &content_text
         })
     }
 
     fn get_recent_user_message(&self) -> Option<String> {
         self.messages.last().and_then(|msg| {
-            match &msg.content {
+            msg.content.as_ref().and_then(|content| match content {
                 MessageContent::Text(text) => Some(text.clone()),
                 MessageContent::Parts(_) => None, // No user message in parts
-            }
+            })
         })
     }
 
@@ -778,7 +772,8 @@ mod tests {
 
         let message = &deserialized_request.messages[0];
         assert_eq!(message.role, Role::User);
-        if let MessageContent::Text(content) = &message.content {
+        assert!(message.content.is_some());
+        if let Some(MessageContent::Text(content)) = &message.content {
             assert_eq!(content, "Hello, world!");
         } else {
             panic!("Expected text content");
@@ -822,7 +817,8 @@ mod tests {
 
         let message = &deserialized_request.messages[0];
         assert_eq!(message.role, Role::User);
-        if let MessageContent::Text(content) = &message.content {
+        assert!(message.content.is_some());
+        if let Some(MessageContent::Text(content)) = &message.content {
             assert_eq!(content, "Test message");
         } else {
             panic!("Expected text content");
@@ -947,7 +943,8 @@ mod tests {
         // Validate first message (user with multimodal content)
         let user_message = &deserialized_request.messages[0];
         assert_eq!(user_message.role, Role::User);
-        if let MessageContent::Parts(ref content_parts) = user_message.content {
+        assert!(user_message.content.is_some());
+        if let Some(MessageContent::Parts(ref content_parts)) = user_message.content {
             assert_eq!(content_parts.len(), 2);
 
             // Validate text content part
@@ -971,7 +968,8 @@ mod tests {
         // Validate second message (assistant with tool calls)
         let assistant_message = &deserialized_request.messages[1];
         assert_eq!(assistant_message.role, Role::Assistant);
-        if let MessageContent::Text(text) = &assistant_message.content {
+        assert!(assistant_message.content.is_some());
+        if let Some(MessageContent::Text(text)) = &assistant_message.content {
             assert_eq!(
                 text,
                 "I can see a beautiful cityscape. Let me check the weather for you."
@@ -997,7 +995,8 @@ mod tests {
         // Validate third message (tool response)
         let tool_message = &deserialized_request.messages[2];
         assert_eq!(tool_message.role, Role::Tool);
-        if let MessageContent::Text(text) = &tool_message.content {
+        assert!(tool_message.content.is_some());
+        if let Some(MessageContent::Text(text)) = &tool_message.content {
             assert_eq!(text, "Current weather in New York: 72°F, sunny");
         } else {
             panic!("Expected text content for tool message");
@@ -1061,6 +1060,62 @@ mod tests {
         assert!((original_temp - serialized_temp).abs() < 1e-6);
     }
 
+    #[test]
+    fn test_assistant_message_with_tool_calls_no_content() {
+        // Test that assistant messages can have tool_calls without content
+        let json_with_tool_calls_no_content = json!({
+            "model": "gpt-4",
+            "messages": [
+                {
+                    "role": "user",
+                    "content": "What's the weather in San Francisco?"
+                },
+                {
+                    "role": "assistant",
+                    "tool_calls": [
+                        {
+                            "id": "call_123",
+                            "type": "function",
+                            "function": {
+                                "name": "get_weather",
+                                "arguments": "{\"location\": \"San Francisco, CA\"}"
+                            }
+                        }
+                    ]
+                }
+            ]
+        });
+
+        // Should deserialize successfully
+        let request: ChatCompletionsRequest =
+            serde_json::from_value(json_with_tool_calls_no_content.clone()).unwrap();
+
+        assert_eq!(request.messages.len(), 2);
+
+        // Check user message
+        let user_msg = &request.messages[0];
+        assert_eq!(user_msg.role, Role::User);
+        assert!(user_msg.content.is_some());
+
+        // Check assistant message - should have tool_calls but no content
+        let assistant_msg = &request.messages[1];
+        assert_eq!(assistant_msg.role, Role::Assistant);
+        assert!(assistant_msg.content.is_none());
+        assert!(assistant_msg.tool_calls.is_some());
+
+        let tool_calls = assistant_msg.tool_calls.as_ref().unwrap();
+        assert_eq!(tool_calls.len(), 1);
+        assert_eq!(tool_calls[0].id, "call_123");
+        assert_eq!(tool_calls[0].function.name, "get_weather");
+
+        // Should serialize back without content field
+        let serialized = serde_json::to_value(&request).unwrap();
+        // Verify the assistant message doesn't have a content field in serialized JSON
+        let serialized_assistant_msg = &serialized["messages"][1];
+        assert!(serialized_assistant_msg.get("content").is_none());
+        assert!(serialized_assistant_msg.get("tool_calls").is_some());
+    }
+
     #[test]
     fn test_api_provider_trait() {
         // Test the ApiDefinition trait implementation
@@ -1097,7 +1152,7 @@ mod tests {
 
         let deserialized_user: Message = serde_json::from_value(user_json.clone()).unwrap();
         assert_eq!(deserialized_user.role, Role::User);
-        if let MessageContent::Text(content) = &deserialized_user.content {
+        if let Some(MessageContent::Text(content)) = &deserialized_user.content {
             assert_eq!(content, "Hello!");
         } else {
             panic!("Expected text content");
@@ -1128,7 +1183,7 @@ mod tests {
         let deserialized_assistant: Message =
             serde_json::from_value(assistant_json.clone()).unwrap();
         assert_eq!(deserialized_assistant.role, Role::Assistant);
-        if let MessageContent::Text(content) = &deserialized_assistant.content {
+        if let Some(MessageContent::Text(content)) = &deserialized_assistant.content {
             assert_eq!(content, "I'll help with that.");
         } else {
             panic!("Expected text content");
@@ -1154,7 +1209,7 @@ mod tests {
 
         let deserialized_tool: Message = serde_json::from_value(tool_json.clone()).unwrap();
         assert_eq!(deserialized_tool.role, Role::Tool);
-        if let MessageContent::Text(content) = &deserialized_tool.content {
+        if let Some(MessageContent::Text(content)) = &deserialized_tool.content {
             assert_eq!(content, "Weather is sunny");
         } else {
             panic!("Expected text content");
@@ -1193,7 +1248,7 @@ mod tests {
         // Test conversion from ResponseMessage to Message
         let converted = deserialized_response.to_message();
         assert_eq!(converted.role, Role::Assistant);
-        if let MessageContent::Text(text) = converted.content {
+        if let Some(MessageContent::Text(text)) = converted.content {
             assert_eq!(text, "Response content");
         } else {
             panic!("Expected text content");
diff --git a/crates/hermesllm/src/apis/openai_responses.rs b/crates/hermesllm/src/apis/openai_responses.rs
index 720e24d3..dbc82f8b 100644
--- a/crates/hermesllm/src/apis/openai_responses.rs
+++ b/crates/hermesllm/src/apis/openai_responses.rs
@@ -1146,7 +1146,7 @@ impl ProviderRequest for ResponsesAPIRequest {
             .iter()
             .filter(|msg| msg.role == crate::apis::openai::Role::System)
             .filter_map(|msg| {
-                if let crate::apis::openai::MessageContent::Text(text) = &msg.content {
+                if let Some(crate::apis::openai::MessageContent::Text(text)) = &msg.content {
                     Some(text.as_str())
                 } else {
                     None
@@ -1170,7 +1170,8 @@ impl ProviderRequest for ResponsesAPIRequest {
         if !input_messages.is_empty() {
             // If there's only one message, use Text format
             if input_messages.len() == 1 {
-                if let crate::apis::openai::MessageContent::Text(text) = &input_messages[0].content
+                if let Some(crate::apis::openai::MessageContent::Text(text)) =
+                    &input_messages[0].content
                 {
                     self.input = crate::apis::openai_responses::InputParam::Text(text.clone());
                 }
@@ -1180,7 +1181,8 @@ impl ProviderRequest for ResponsesAPIRequest {
                 let combined_text = input_messages
                     .iter()
                     .filter_map(|msg| {
-                        if let crate::apis::openai::MessageContent::Text(text) = &msg.content {
+                        if let Some(crate::apis::openai::MessageContent::Text(text)) = &msg.content
+                        {
                             Some(format!(
                                 "{}: {}",
                                 match msg.role {
diff --git a/crates/hermesllm/src/providers/request.rs b/crates/hermesllm/src/providers/request.rs
index d1d85888..e97e8a68 100644
--- a/crates/hermesllm/src/providers/request.rs
+++ b/crates/hermesllm/src/providers/request.rs
@@ -671,14 +671,16 @@ mod tests {
             messages: vec![
                 Message {
                     role: Role::System,
-                    content: MessageContent::Text("You are a helpful assistant".to_string()),
+                    content: Some(MessageContent::Text(
+                        "You are a helpful assistant".to_string(),
+                    )),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
                 },
                 Message {
                     role: Role::User,
-                    content: MessageContent::Text("Hello!".to_string()),
+                    content: Some(MessageContent::Text("Hello!".to_string())),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
@@ -900,7 +902,7 @@ mod tests {
             model: "gpt-4".to_string(),
             messages: vec![Message {
                 role: Role::User,
-                content: MessageContent::Text("Hello!".to_string()),
+                content: Some(MessageContent::Text("Hello!".to_string())),
                 name: None,
                 tool_calls: None,
                 tool_call_id: None,
@@ -993,14 +995,14 @@ mod tests {
             messages: vec![
                 Message {
                     role: Role::System,
-                    content: MessageContent::Text("You are helpful".to_string()),
+                    content: Some(MessageContent::Text("You are helpful".to_string())),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
                 },
                 Message {
                     role: Role::User,
-                    content: MessageContent::Text("Hello!".to_string()),
+                    content: Some(MessageContent::Text("Hello!".to_string())),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
diff --git a/crates/hermesllm/src/transforms/lib.rs b/crates/hermesllm/src/transforms/lib.rs
index a44f8d79..115f061c 100644
--- a/crates/hermesllm/src/transforms/lib.rs
+++ b/crates/hermesllm/src/transforms/lib.rs
@@ -188,7 +188,7 @@ pub fn convert_openai_message_to_anthropic_content(
 
     // Handle regular content
     match &message.content {
-        MessageContent::Text(text) => {
+        Some(MessageContent::Text(text)) => {
             if !text.is_empty() {
                 blocks.push(MessagesContentBlock::Text {
                     text: text.clone(),
@@ -196,7 +196,7 @@ pub fn convert_openai_message_to_anthropic_content(
                 });
             }
         }
-        MessageContent::Parts(parts) => {
+        Some(MessageContent::Parts(parts)) => {
             for part in parts {
                 match part {
                     ContentPart::Text { text } => {
@@ -212,6 +212,7 @@ pub fn convert_openai_message_to_anthropic_content(
                 }
             }
         }
+        None => {}
     }
 
     // Handle tool calls
diff --git a/crates/hermesllm/src/transforms/request/from_anthropic.rs b/crates/hermesllm/src/transforms/request/from_anthropic.rs
index c07be4e5..82dbe547 100644
--- a/crates/hermesllm/src/transforms/request/from_anthropic.rs
+++ b/crates/hermesllm/src/transforms/request/from_anthropic.rs
@@ -174,7 +174,7 @@ impl TryFrom<MessagesMessage> for Vec<Message> {
             MessagesMessageContent::Single(text) => {
                 result.push(Message {
                     role: message.role.into(),
-                    content: MessageContent::Text(text),
+                    content: Some(MessageContent::Text(text)),
                     name: None,
                     tool_calls: None,
                     tool_call_id: None,
@@ -186,7 +186,7 @@ impl TryFrom<MessagesMessage> for Vec<Message> {
                 for (tool_use_id, result_text, _is_error) in tool_results {
                     result.push(Message {
                         role: Role::Tool,
-                        content: MessageContent::Text(result_text),
+                        content: Some(MessageContent::Text(result_text)),
                         name: None,
                         tool_calls: None,
                         tool_call_id: Some(tool_use_id),
@@ -260,7 +260,7 @@ impl From<MessagesSystemPrompt> for Message {
 
         Message {
             role: Role::System,
-            content: system_content,
+            content: Some(system_content),
             name: None,
             tool_calls: None,
             tool_call_id: None,
@@ -317,16 +317,19 @@ fn convert_anthropic_tool_choice(
 fn build_openai_content(
     content_parts: Vec<ContentPart>,
     tool_calls: &[ToolCall],
-) -> MessageContent {
-    if content_parts.len() == 1 && tool_calls.is_empty() {
+) -> Option<MessageContent> {
+    if content_parts.is_empty() && !tool_calls.is_empty() {
+        // For assistant messages with only tool calls, content is optional
+        None
+    } else if content_parts.len() == 1 && tool_calls.is_empty() {
         match &content_parts[0] {
-            ContentPart::Text { text } => MessageContent::Text(text.clone()),
-            _ => MessageContent::Parts(content_parts),
+            ContentPart::Text { text } => Some(MessageContent::Text(text.clone())),
+            _ => Some(MessageContent::Parts(content_parts)),
         }
     } else if content_parts.is_empty() {
-        MessageContent::Text("".to_string())
+        Some(MessageContent::Text("".to_string()))
     } else {
-        MessageContent::Parts(content_parts)
+        Some(MessageContent::Parts(content_parts))
     }
 }
 
diff --git a/crates/hermesllm/src/transforms/request/from_openai.rs b/crates/hermesllm/src/transforms/request/from_openai.rs
index e39cfed3..ddc3b1ca 100644
--- a/crates/hermesllm/src/transforms/request/from_openai.rs
+++ b/crates/hermesllm/src/transforms/request/from_openai.rs
@@ -18,7 +18,6 @@ use crate::apis::openai_responses::{
     ResponsesAPIRequest, Tool as ResponsesTool, ToolChoice as ResponsesToolChoice,
 };
 use crate::clients::TransformError;
-use crate::transforms::lib::ExtractText;
 use crate::transforms::lib::*;
 use crate::transforms::*;
 
@@ -48,7 +47,7 @@ impl TryFrom<ResponsesInputConverter> for Vec<Message> {
                 if let Some(instructions) = converter.instructions {
                     messages.push(Message {
                         role: Role::System,
-                        content: MessageContent::Text(instructions),
+                        content: Some(MessageContent::Text(instructions)),
                         name: None,
                         tool_call_id: None,
                         tool_calls: None,
@@ -58,7 +57,7 @@ impl TryFrom<ResponsesInputConverter> for Vec<Message> {
                 // Add the user message
                 messages.push(Message {
                     role: Role::User,
-                    content: MessageContent::Text(text),
+                    content: Some(MessageContent::Text(text)),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
@@ -74,7 +73,7 @@ impl TryFrom<ResponsesInputConverter> for Vec<Message> {
                 if let Some(instructions) = converter.instructions {
                     converted_messages.push(Message {
                         role: Role::System,
-                        content: MessageContent::Text(instructions),
+                        content: Some(MessageContent::Text(instructions)),
                         name: None,
                         tool_call_id: None,
                         tool_calls: None,
@@ -154,7 +153,7 @@ impl TryFrom<ResponsesInputConverter> for Vec<Message> {
 
                         converted_messages.push(Message {
                             role,
-                            content,
+                            content: Some(content),
                             name: None,
                             tool_call_id: None,
                             tool_calls: None,
@@ -174,11 +173,7 @@ impl TryFrom<ResponsesInputConverter> for Vec<Message> {
 
 impl From<Message> for MessagesSystemPrompt {
     fn from(val: Message) -> Self {
-        let system_text = match val.content {
-            MessageContent::Text(text) => text,
-            MessageContent::Parts(parts) => parts.extract_text(),
-        };
-        MessagesSystemPrompt::Single(system_text)
+        MessagesSystemPrompt::Single(val.content.extract_text())
     }
 }
 
@@ -191,6 +186,8 @@ impl TryFrom<Message> for MessagesMessage {
             Role::Assistant => MessagesRole::Assistant,
             Role::Tool => {
                 // Tool messages become user messages with tool results
+                // Extract content text first, before moving tool_call_id
+                let content_text = message.content.extract_text();
                 let tool_call_id = message.tool_call_id.ok_or_else(|| {
                     TransformError::MissingField(
                         "tool_call_id required for Tool messages".to_string(),
@@ -204,7 +201,7 @@ impl TryFrom<Message> for MessagesMessage {
                             tool_use_id: tool_call_id,
                             is_error: None,
                             content: ToolResultContent::Blocks(vec![MessagesContentBlock::Text {
-                                text: message.content.extract_text(),
+                                text: content_text,
                                 cache_control: None,
                             }]),
                             cache_control: None,
@@ -248,12 +245,12 @@ impl TryFrom<Message> for BedrockMessage {
             Role::User => {
                 // Convert user message content to content blocks
                 match message.content {
-                    MessageContent::Text(text) => {
+                    Some(MessageContent::Text(text)) => {
                         if !text.is_empty() {
                             content_blocks.push(ContentBlock::Text { text });
                         }
                     }
-                    MessageContent::Parts(parts) => {
+                    Some(MessageContent::Parts(parts)) => {
                         // Convert OpenAI content parts to Bedrock ContentBlocks
                         for part in parts {
                             match part {
@@ -293,6 +290,9 @@ impl TryFrom<Message> for BedrockMessage {
                             }
                         }
                     }
+                    None => {
+                        // Empty content for user - shouldn't happen but handle gracefully
+                    }
                 }
 
                 // Ensure we have at least one content block
@@ -550,10 +550,7 @@ impl TryFrom<ChatCompletionsRequest> for ConverseRequest {
         for message in req.messages {
             match message.role {
                 Role::System => {
-                    let system_text = match message.content {
-                        MessageContent::Text(text) => text,
-                        MessageContent::Parts(parts) => parts.extract_text(),
-                    };
+                    let system_text = message.content.extract_text();
                     system_messages.push(SystemContentBlock::Text { text: system_text });
                 }
                 _ => {
@@ -778,14 +775,16 @@ mod tests {
             messages: vec![
                 Message {
                     role: Role::System,
-                    content: MessageContent::Text("You are a helpful assistant.".to_string()),
+                    content: Some(MessageContent::Text(
+                        "You are a helpful assistant.".to_string(),
+                    )),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
                 },
                 Message {
                     role: Role::User,
-                    content: MessageContent::Text("Hello, how are you?".to_string()),
+                    content: Some(MessageContent::Text("Hello, how are you?".to_string())),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
@@ -840,7 +839,7 @@ mod tests {
             model: "gpt-4".to_string(),
             messages: vec![Message {
                 role: Role::User,
-                content: MessageContent::Text("What's the weather like?".to_string()),
+                content: Some(MessageContent::Text("What's the weather like?".to_string())),
                 name: None,
                 tool_call_id: None,
                 tool_calls: None,
@@ -907,7 +906,7 @@ mod tests {
             model: "gpt-4".to_string(),
             messages: vec![Message {
                 role: Role::User,
-                content: MessageContent::Text("Help me with something".to_string()),
+                content: Some(MessageContent::Text("Help me with something".to_string())),
                 name: None,
                 tool_call_id: None,
                 tool_calls: None,
@@ -950,28 +949,30 @@ mod tests {
             messages: vec![
                 Message {
                     role: Role::System,
-                    content: MessageContent::Text("Be concise".to_string()),
+                    content: Some(MessageContent::Text("Be concise".to_string())),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
                 },
                 Message {
                     role: Role::User,
-                    content: MessageContent::Text("Hello".to_string()),
+                    content: Some(MessageContent::Text("Hello".to_string())),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
                 },
                 Message {
                     role: Role::Assistant,
-                    content: MessageContent::Text("Hi there! How can I help you?".to_string()),
+                    content: Some(MessageContent::Text(
+                        "Hi there! How can I help you?".to_string(),
+                    )),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
                 },
                 Message {
                     role: Role::User,
-                    content: MessageContent::Text("What's 2+2?".to_string()),
+                    content: Some(MessageContent::Text("What's 2+2?".to_string())),
                     name: None,
                     tool_call_id: None,
                     tool_calls: None,
@@ -1009,7 +1010,7 @@ mod tests {
     fn test_openai_message_to_bedrock_conversion() {
         let openai_message = Message {
             role: Role::User,
-            content: MessageContent::Text("Test message".to_string()),
+            content: Some(MessageContent::Text("Test message".to_string())),
             name: None,
             tool_call_id: None,
             tool_calls: None,
diff --git a/tests/e2e/test_model_alias_routing.py b/tests/e2e/test_model_alias_routing.py
index 7af14df1..f20c24af 100644
--- a/tests/e2e/test_model_alias_routing.py
+++ b/tests/e2e/test_model_alias_routing.py
@@ -22,6 +22,81 @@ LLM_GATEWAY_ENDPOINT = os.getenv(
 # =============================================================================
 
 
+def test_assistant_message_with_null_content_and_tool_calls():
+    """Test that assistant messages with null content and tool_calls are properly handled"""
+    logger.info(
+        "Testing assistant message with null content and tool_calls (multi-turn conversation)"
+    )
+
+    base_url = LLM_GATEWAY_ENDPOINT.replace("/v1/chat/completions", "")
+    client = openai.OpenAI(
+        api_key="test-key",
+        base_url=f"{base_url}/v1",
+    )
+
+    # Simulate a multi-turn conversation where:
+    # 1. User asks a question
+    # 2. Assistant makes a tool call (with null content)
+    # 3. Tool responds
+    # 4. Assistant should provide final answer
+    completion = client.chat.completions.create(
+        model="gpt-4o",
+        max_tokens=500,
+        messages=[
+            {
+                "role": "system",
+                "content": "You are a weather assistant. Use the get_weather tool to fetch weather information.",
+            },
+            {"role": "user", "content": "What's the weather in Seattle?"},
+            {
+                "role": "assistant",
+                "content": None,  # This is the key test - null content with tool_calls
+                "tool_calls": [
+                    {
+                        "id": "call_test123",
+                        "type": "function",
+                        "function": {
+                            "name": "get_weather",
+                            "arguments": '{"city": "Seattle"}',
+                        },
+                    }
+                ],
+            },
+            {
+                "role": "tool",
+                "tool_call_id": "call_test123",
+                "content": '{"location": "Seattle", "temperature": "10°C", "condition": "Partly cloudy"}',
+            },
+        ],
+        tools=[
+            {
+                "type": "function",
+                "function": {
+                    "name": "get_weather",
+                    "description": "Get weather information for a city",
+                    "parameters": {
+                        "type": "object",
+                        "properties": {
+                            "city": {"type": "string", "description": "City name"}
+                        },
+                        "required": ["city"],
+                    },
+                },
+            }
+        ],
+    )
+
+    response_content = completion.choices[0].message.content
+    logger.info(f"Response after tool call: {response_content}")
+
+    # The assistant should provide a final response using the tool result
+    assert response_content is not None
+    assert len(response_content) > 0
+    logger.info(
+        "✓ Assistant message with null content and tool_calls handled correctly"
+    )
+
+
 def test_openai_client_with_alias_arch_summarize_v1():
     """Test OpenAI client using model alias 'arch.summarize.v1' which should resolve to '4o-mini'"""
     logger.info("Testing OpenAI client with alias 'arch.summarize.v1' -> '4o-mini'")