diff --git a/src/agent/api/types.rs b/src/agent/api/types.rs
index a875b54..ce79cdf 100644
--- a/src/agent/api/types.rs
+++ b/src/agent/api/types.rs
@@ -103,7 +103,7 @@ pub struct Message {
     pub timestamp: Option<String>,
 }
 
-#[derive(Debug, Clone, Serialize, Deserialize, PartialEq)]
+#[derive(Debug, Copy, Clone, Serialize, Deserialize, PartialEq)]
 #[serde(rename_all = "lowercase")]
 pub enum Role {
     System,
diff --git a/src/user/chat.rs b/src/user/chat.rs
index 61d2c7e..8078ec8 100644
--- a/src/user/chat.rs
+++ b/src/user/chat.rs
@@ -13,6 +13,7 @@ use ratatui::{
 };
 
 use super::{App, ScreenView, screen_legend};
+use crate::agent::api::Role;
 use crate::mind::MindCommand;
 
 // --- Slash command table ---
@@ -477,12 +478,23 @@ impl InteractScreen {
                 self.tools = PaneState::new(false);
                 self.last_entries.clear();
             } else {
-                // Pop entries from the tail that don't match
-                while !self.last_entries.is_empty() {
-                    let i = self.last_entries.len() - 1;
-                    if entries.get(i) == Some(&self.last_entries[i]) {
+                let mut pop = self.last_entries.len();
+
+                for i in (0..self.last_entries.len()).rev() {
+                    // Check if this entry is out of bounds or doesn't match
+                    let matches = i < entries.len() && self.last_entries[i] == entries[i];
+                    
+                    if !matches {
+                        pop = i;
+                    }
+                    
+                    // Only stop at assistant if it matches - otherwise keep going
+                    if matches && self.last_entries[i].message().role == Role::Assistant {
                         break;
                     }
+                }
+                
+                while self.last_entries.len() > pop {
                     let popped = self.last_entries.pop().unwrap();
                     for (target, _, _) in Self::route_entry(&popped) {
                         match target {
@@ -563,7 +575,6 @@ impl InteractScreen {
         let _ = self.mind_tx.send(MindCommand::None);
     }
 
-
     fn scroll_active_up(&mut self, n: u16) {
         match self.active_pane {
             ActivePane::Autonomous => self.autonomous.scroll_up(n),