diff --git a/crates/goose/src/conversation_fixer.rs b/crates/goose/src/conversation_fixer.rs
index 9eb2b80b539e..1a585ae699d1 100644
--- a/crates/goose/src/conversation_fixer.rs
+++ b/crates/goose/src/conversation_fixer.rs
@@ -10,11 +10,11 @@ impl ConversationFixer {
     /// Fix a conversation that we're about to send to an LLM. So the last and first
     /// messages should always be from the user.
     pub fn fix_conversation(messages: Vec<Message>) -> (Vec<Message>, Vec<String>) {
-        let (messages, empty_removed) = Self::remove_empty_messages(messages);
-        let (messages, tool_calling_fixed) = Self::fix_tool_calling(messages);
-        let (messages, messages_merged) = Self::merge_consecutive_messages(messages);
-        let (messages, lead_trail_fixed) = Self::fix_lead_trail(messages);
-        let (messages, populated_if_empty) = Self::populate_if_empty(messages);
+        let (messages_1, empty_removed) = Self::remove_empty_messages(messages);
+        let (messages_2, tool_calling_fixed) = Self::fix_tool_calling(messages_1);
+        let (messages_3, messages_merged) = Self::merge_consecutive_messages(messages_2);
+        let (messages_4, lead_trail_fixed) = Self::fix_lead_trail(messages_3);
+        let (messages_5, populated_if_empty) = Self::populate_if_empty(messages_4);
 
         let mut issues = Vec::new();
         issues.extend(empty_removed);
@@ -23,7 +23,7 @@ impl ConversationFixer {
         issues.extend(lead_trail_fixed);
         issues.extend(populated_if_empty);
 
-        (messages, issues)
+        (messages_5, issues)
     }
 
     fn remove_empty_messages(messages: Vec<Message>) -> (Vec<Message>, Vec<String>) {
@@ -145,13 +145,10 @@ impl ConversationFixer {
 
         for message in messages {
             if let Some(last) = merged_messages.last_mut() {
-                if last.role == message.role {
+                let effective = Self::effective_role(&message);
+                if Self::effective_role(last) == effective {
                     last.content.extend(message.content);
-                    let role_name = match message.role {
-                        Role::User => "user",
-                        Role::Assistant => "assistant",
-                    };
-                    issues.push(format!("Merged consecutive {} messages", role_name));
+                    issues.push(format!("Merged consecutive {} messages", effective));
                     continue;
                 }
             }
@@ -161,6 +158,24 @@ impl ConversationFixer {
         (merged_messages, issues)
     }
 
+    fn has_tool_response(message: &Message) -> bool {
+        message
+            .content
+            .iter()
+            .any(|content| matches!(content, MessageContent::ToolResponse(_)))
+    }
+
+    fn effective_role(message: &Message) -> String {
+        if message.role == Role::User && Self::has_tool_response(message) {
+            "tool".to_string()
+        } else {
+            match message.role {
+                Role::User => "user".to_string(),
+                Role::Assistant => "assistant".to_string(),
+            }
+        }
+    }
+
     fn fix_lead_trail(mut messages: Vec<Message>) -> (Vec<Message>, Vec<String>) {
         let mut issues = Vec::new();
 
@@ -375,4 +390,19 @@ mod tests {
         assert!(issues[0].contains("Removed orphaned tool request"));
         assert!(issues[1].contains("Merged consecutive assistant messages"));
     }
+
+    #[test]
+    fn test_tool_response_effective_role() {
+        let messages = vec![
+            Message::user().with_text("Search for something"),
+            Message::assistant()
+                .with_text("I'll search for you")
+                .with_tool_request("search_1", Ok(ToolCall::new("search", json!({})))),
+            Message::user().with_tool_response("search_1", Ok(vec![])),
+            Message::user().with_text("Thanks!"),
+        ];
+
+        let (fixed, issues) = run_verify(messages);
+        assert_eq!(issues.len(), 0);
+    }
 }