diff --git a/crates/goose/src/providers/formats/google.rs b/crates/goose/src/providers/formats/google.rs
index 0ebd134c66..ce652db9d0 100644
--- a/crates/goose/src/providers/formats/google.rs
+++ b/crates/goose/src/providers/formats/google.rs
@@ -31,7 +31,7 @@ pub fn get_thought_signature(metadata: &Option<ProviderMetadata>) -> Option<&str
 
 /// Convert internal Message format to Google's API message specification
 pub fn format_messages(messages: &[Message]) -> Vec<Value> {
-    messages
+    let filtered: Vec<_> = messages
         .iter()
         .filter(|m| m.is_agent_visible())
         .filter(|message| {
@@ -42,12 +42,28 @@ pub fn format_messages(messages: &[Message]) -> Vec<Value> {
                 )
             })
         })
-        .map(|message| {
+        .collect();
+
+    let last_assistant_idx = filtered
+        .iter()
+        .enumerate()
+        .filter(|(_, m)| m.role != Role::User)
+        .map(|(i, _)| i)
+        .next_back();
+
+    filtered
+        .iter()
+        .enumerate()
+        .map(|(idx, message)| {
             let role = if message.role == Role::User {
                 "user"
             } else {
                 "model"
             };
+            let include_signature = match last_assistant_idx {
+                Some(last_idx) => idx >= last_idx,
+                None => false,
+            };
             let mut parts = Vec::new();
             for message_content in message.content.iter() {
                 match message_content {
@@ -74,8 +90,13 @@ pub fn format_messages(messages: &[Message]) -> Vec<Value> {
                             let mut part = Map::new();
                             part.insert("functionCall".to_string(), json!(function_call_part));
 
-                            if let Some(signature) = get_thought_signature(&request.metadata) {
-                                part.insert(THOUGHT_SIGNATURE_KEY.to_string(), json!(signature));
+                            if include_signature {
+                                if let Some(signature) = get_thought_signature(&request.metadata) {
+                                    part.insert(
+                                        THOUGHT_SIGNATURE_KEY.to_string(),
+                                        json!(signature),
+                                    );
+                                }
                             }
 
                             parts.push(json!(part));
@@ -144,11 +165,15 @@ pub fn format_messages(messages: &[Message]) -> Vec<Value> {
                                     "functionResponse".to_string(),
                                     json!(function_response),
                                 );
-                                if let Some(signature) = get_thought_signature(&response.metadata) {
-                                    part.insert(
-                                        THOUGHT_SIGNATURE_KEY.to_string(),
-                                        json!(signature),
-                                    );
+                                if include_signature {
+                                    if let Some(signature) =
+                                        get_thought_signature(&response.metadata)
+                                    {
+                                        part.insert(
+                                            THOUGHT_SIGNATURE_KEY.to_string(),
+                                            json!(signature),
+                                        );
+                                    }
                                 }
                                 parts.push(json!(part));
                             }
@@ -164,11 +189,15 @@ pub fn format_messages(messages: &[Message]) -> Vec<Value> {
                                     "functionResponse".to_string(),
                                     json!(function_response),
                                 );
-                                if let Some(signature) = get_thought_signature(&response.metadata) {
-                                    part.insert(
-                                        THOUGHT_SIGNATURE_KEY.to_string(),
-                                        json!(signature),
-                                    );
+                                if include_signature {
+                                    if let Some(signature) =
+                                        get_thought_signature(&response.metadata)
+                                    {
+                                        part.insert(
+                                            THOUGHT_SIGNATURE_KEY.to_string(),
+                                            json!(signature),
+                                        );
+                                    }
                                 }
                                 parts.push(json!(part));
                             }
@@ -177,7 +206,9 @@ pub fn format_messages(messages: &[Message]) -> Vec<Value> {
                     MessageContent::Thinking(thinking) => {
                         let mut part = Map::new();
                         part.insert("text".to_string(), json!(thinking.thinking));
-                        part.insert("thoughtSignature".to_string(), json!(thinking.signature));
+                        if include_signature {
+                            part.insert("thoughtSignature".to_string(), json!(thinking.signature));
+                        }
                         parts.push(json!(part));
                     }
 
@@ -1230,10 +1261,21 @@ mod tests {
             Ok(tool_result("output")),
             req1.metadata.as_ref(),
         );
-        let google_out = format_messages(&[native, tool_response]);
+        let google_out = format_messages(&[native.clone(), tool_response.clone()]);
         assert_eq!(google_out[0]["parts"][0]["thoughtSignature"], SIG);
         assert_eq!(google_out[1]["parts"][0]["thoughtSignature"], SIG);
 
+        let second_assistant =
+            Message::assistant().with_thinking("More thinking".to_string(), "sig_456".to_string());
+        let google_multi = format_messages(&[native, tool_response, second_assistant]);
+        assert!(google_multi[0]["parts"][0]
+            .get("thoughtSignature")
+            .is_none());
+        assert!(google_multi[1]["parts"][0]
+            .get("thoughtSignature")
+            .is_none());
+        assert_eq!(google_multi[2]["parts"][0]["thoughtSignature"], "sig_456");
+
         // Text-only response WITH signature but WITHOUT function calls should be regular text
         // (per original behavior: thinking is only when reasoning before tool calls)
         let final_response_with_sig =