diff --git a/src/storied/cli.py b/src/storied/cli.py
index 3d00387..d305d72 100644
--- a/src/storied/cli.py
+++ b/src/storied/cli.py
@@ -499,6 +499,9 @@ def cmd_play(args: argparse.Namespace) -> int:
                             console.file.write("\n\n")
                         console.print(f"[dim]{chunk}[/dim]")
                         prev_type = "tool"
+                    elif chunk == "":
+                        # Flush signal from engine (deferred tool starting)
+                        renderer.flush()
                     else:
                         if prev_type == "tool":
                             console.print()
diff --git a/src/storied/engine.py b/src/storied/engine.py
index bfa5476..69a8516 100644
--- a/src/storied/engine.py
+++ b/src/storied/engine.py
@@ -439,6 +439,10 @@ class DMEngine:
                         self.character_created = True
 
                     if short in ("roll", "run_code") and not self.debug:
+                        # Signal the CLI to flush the renderer before we
+                        # wait for tool input (the notification comes at
+                        # ToolStop once we know the reason/description).
+                        yield ""
                         deferred_notification = True
                     elif self.debug:
                         yield f"[→ {short}(...)]"