diff --git a/crates/chat-cli/src/cli/chat/conversation_state.rs b/crates/chat-cli/src/cli/chat/conversation_state.rs
index 23d5fdb434..850eb3278e 100644
--- a/crates/chat-cli/src/cli/chat/conversation_state.rs
+++ b/crates/chat-cli/src/cli/chat/conversation_state.rs
@@ -514,8 +514,8 @@ impl ConversationState {
             .expect("unable to construct conversation state")
     }
 
-    pub async fn update_state(&mut self) {
-        let needs_update = self.tool_manager.has_new_stuff.load(Ordering::Acquire);
+    pub async fn update_state(&mut self, force_update: bool) {
+        let needs_update = self.tool_manager.has_new_stuff.load(Ordering::Acquire) || force_update;
         if !needs_update {
             return;
         }
diff --git a/crates/chat-cli/src/cli/chat/mod.rs b/crates/chat-cli/src/cli/chat/mod.rs
index 2fd1e5dbe7..44ee746696 100644
--- a/crates/chat-cli/src/cli/chat/mod.rs
+++ b/crates/chat-cli/src/cli/chat/mod.rs
@@ -572,7 +572,7 @@ impl ChatContext {
                 cs.reload_serialized_state(Arc::clone(&ctx), Some(output.clone())).await;
                 input = Some(input.unwrap_or("In a few words, summarize our conversation so far.".to_owned()));
                 cs.tool_manager = tool_manager;
-                cs.enforce_tool_use_history_invariants(false);
+                cs.update_state(true).await;
                 cs
             } else {
                 ConversationState::new(
@@ -816,7 +816,7 @@ impl ChatContext {
             debug!(?chat_state, "changing to state");
 
             // Update conversation state with new tool information
-            self.conversation_state.update_state().await;
+            self.conversation_state.update_state(false).await;
 
             let result = match chat_state {
                 ChatState::PromptUser {