diff --git a/src/agent/context.rs b/src/agent/context.rs
index 79ca030..a571203 100644
--- a/src/agent/context.rs
+++ b/src/agent/context.rs
@@ -795,6 +795,88 @@ impl ContextState {
         self.section_mut(section).clear();
     }
 
+    /// Dedup and trim conversation entries to fit within the context budget.
+    ///
+    /// Phase 1: Drop duplicate memories (keep last) and DMN entries.
+    /// Phase 2: While over budget, drop lowest-scored memory (if memories
+    ///          are > 50% of conversation tokens) or oldest conversation entry.
+    /// Phase 3: Snap to user message boundary at start.
+    pub fn trim_conversation(&mut self) {
+        let max_tokens = context_budget_tokens();
+        let fixed = self.system.iter().map(|n| n.tokens()).sum::<usize>()
+            + self.identity.iter().map(|n| n.tokens()).sum::<usize>()
+            + self.journal.iter().map(|n| n.tokens()).sum::<usize>();
+
+        // Phase 1: dedup memories by key (keep last), drop DMN
+        let mut seen_keys: std::collections::HashMap<String, usize> = std::collections::HashMap::new();
+        let mut drop = std::collections::HashSet::new();
+
+        for (i, node) in self.conversation.iter().enumerate() {
+            if let AstNode::Leaf(leaf) = node {
+                match leaf.body() {
+                    NodeBody::Dmn(_) => { drop.insert(i); }
+                    NodeBody::Memory { key, .. } => {
+                        if let Some(prev) = seen_keys.insert(key.clone(), i) {
+                            drop.insert(prev);
+                        }
+                    }
+                    _ => {}
+                }
+            }
+        }
+
+        if !drop.is_empty() {
+            let mut i = 0;
+            self.conversation.retain(|_| { let keep = !drop.contains(&i); i += 1; keep });
+        }
+
+        // Phase 2: while over budget, evict
+        loop {
+            let total: usize = self.conversation.iter().map(|n| n.tokens()).sum();
+            if fixed + total <= max_tokens { break; }
+            let mt: usize = self.conversation.iter()
+                .filter(|n| matches!(n, AstNode::Leaf(l) if matches!(l.body(), NodeBody::Memory { .. })))
+                .map(|n| n.tokens()).sum();
+            let ct = total - mt;
+
+            if mt > ct {
+                // Memories > 50% — drop lowest-scored
+                if let Some(i) = self.lowest_scored_memory() {
+                    self.conversation.remove(i);
+                    continue;
+                }
+            }
+            // Drop oldest non-memory entry
+            if let Some(i) = self.conversation.iter().position(|n|
+                !matches!(n, AstNode::Leaf(l) if matches!(l.body(), NodeBody::Memory { .. })))
+            {
+                self.conversation.remove(i);
+            } else {
+                break;
+            }
+        }
+
+        // Phase 3: snap to user message boundary
+        while let Some(first) = self.conversation.first() {
+            if matches!(first, AstNode::Branch { role: Role::User, .. }) { break; }
+            self.conversation.remove(0);
+        }
+    }
+
+    fn lowest_scored_memory(&self) -> Option<usize> {
+        self.conversation.iter().enumerate()
+            .filter_map(|(i, n)| {
+                if let AstNode::Leaf(l) = n {
+                    if let NodeBody::Memory { score: Some(s), .. } = l.body() {
+                        return Some((i, *s));
+                    }
+                }
+                None
+            })
+            .min_by(|(_, a), (_, b)| a.partial_cmp(b).unwrap_or(std::cmp::Ordering::Equal))
+            .map(|(i, _)| i)
+    }
+
     /// Push a child node into a branch at `index` in `section`.
     pub fn push_child(&mut self, section: Section, index: usize, child: AstNode) {
         let node = &mut self.section_mut(section)[index];
diff --git a/src/agent/mod.rs b/src/agent/mod.rs
index 8390ec4..b9b1d9b 100644
--- a/src/agent/mod.rs
+++ b/src/agent/mod.rs
@@ -555,6 +555,8 @@ impl Agent {
 
         self.load_startup_journal().await;
 
+        self.context.lock().await.trim_conversation();
+
         let mut st = self.state.lock().await;
         st.generation += 1;
         st.last_prompt_tokens = 0;