diff --git a/README.md b/README.md
index 37cdfda..97343ce 100644
--- a/README.md
+++ b/README.md
@@ -221,7 +221,7 @@ Reading is destructive only through a drain: an agent that reads its mail and th
 ### Bounds
 
 - A single message body is capped at 64 KiB (`ErrBodyTooLarge` if exceeded).
-- One agent's pending mail is capped at 500 messages. Past that, the **oldest** message is dropped first — a silent agent loses its stalest context, never the message that just arrived.
+- One agent's pending mail is capped at 500 messages. Past that, the oldest **`note`** is dropped first; `handoff`/`question`/`answer` only start dropping once every pending `note` is gone. Either way, it's oldest-first within that group — a silent agent loses its stalest context, never the message that just arrived.
 - Every drop increments a per-agent dropped counter, surfaced by `tether ls` (the `PENDING` column, as `N (+M dropped)`), `tether explain`, and `tether inbox`'s stderr warning. Degradation is visible, never silent, and the counter resets to zero the next time that agent actually drains its inbox.
 - Unacked mail nobody ever comes back for is swept and marked dead after 24 hours instead of kept forever. Read-or-dead mail older than **7 days** is then deleted outright in the same background sweep, so the database doesn't grow without bound. No `VACUUM` runs; SQLite reuses the freed space, so the file plateaus rather than shrinks.
 - `tether doctor` reports the database's file path, its size on disk, row counts for messages, agents, and observations, and the daemon log path — so "is my DB getting too big" has a direct answer.
diff --git a/internal/store/messages_test.go b/internal/store/messages_test.go
index 3ea4882..10d1748 100644
--- a/internal/store/messages_test.go
+++ b/internal/store/messages_test.go
@@ -975,6 +975,43 @@ func TestSendEnforcesInboxDepthDropsOldest(t *testing.T) {
 	}
 }
 
+// TestSendEnforcesInboxDepthPrefersDroppingNotes sends a handoff first, then
+// floods the inbox past the cap with notes. Eviction must take the oldest
+// notes, not the oldest message overall -- the handoff survives regardless
+// of its age.
+func TestSendEnforcesInboxDepthPrefersDroppingNotes(t *testing.T) {
+	ctx := context.Background()
+	s := newStore(t)
+	pair(t, s)
+
+	handoff := note("the actual task")
+	handoff.Kind = KindHandoff
+	handoffID := mustSend(t, s, handoff)
+
+	const over = 5
+	notes := make([]string, 0, maxInboxDepth+over-1)
+	for i := 0; i < maxInboxDepth+over-1; i++ {
+		notes = append(notes, mustSend(t, s, note(fmt.Sprintf("m%d", i))))
+	}
+
+	a, err := s.GetAgent(ctx, "ws", "bob")
+	if err != nil {
+		t.Fatalf("GetAgent: %v", err)
+	}
+	if a.Dropped != over {
+		t.Fatalf("agents.dropped = %d, want %d", a.Dropped, over)
+	}
+
+	pending, err := s.Inbox(ctx, "ws", "bob", maxInboxDepth+1)
+	if err != nil {
+		t.Fatalf("Inbox: %v", err)
+	}
+	wantAlive := append([]string{handoffID}, notes[over:]...)
+	if !equalStrings(ids(pending), wantAlive) {
+		t.Fatalf("pending after drops = %v, want %v", ids(pending), wantAlive)
+	}
+}
+
 func TestSendAtExactlyMaxInboxDepthDropsNothing(t *testing.T) {
 	ctx := context.Background()
 	s := newStore(t)
diff --git a/internal/store/queries.go b/internal/store/queries.go
index 33c0f28..1e06a48 100644
--- a/internal/store/queries.go
+++ b/internal/store/queries.go
@@ -131,12 +131,14 @@ DELETE FROM messages
 WHERE (dead = 1 OR acked_at IS NOT NULL) AND created_at < ?`
 
 	// Subquery, not ORDER BY/LIMIT on UPDATE: modernc.org/sqlite rejects that directly.
+	// Notes are evicted before anything else -- a handoff/question/answer only
+	// goes once every pending note is gone, regardless of age.
 	qDropOldest = `
 UPDATE messages SET dead = 1
 WHERE id IN (
     SELECT id FROM messages
     WHERE to_ws = ? AND to_name = ? AND acked_at IS NULL AND dead = 0
-    ORDER BY id
+    ORDER BY kind = 'note' DESC, id
     LIMIT ?
 )`