diff --git a/src/void_tools/cli.py b/src/void_tools/cli.py
index 1373e05..adac28c 100644
--- a/src/void_tools/cli.py
+++ b/src/void_tools/cli.py
@@ -30,8 +30,6 @@ def mirror_to_letta(text, target_uri):
             "text": f"Margin Annotation attached to {target_uri}: {text}"
         }
         
-        # We need to handle Letta's expected JSON payload which might require a specific format.
-        # The standard endpoint takes {"text": "string"}
         resp = requests.post(url, headers=headers, json=payload)
         if resp.ok:
             print("  Mirrored annotation to Letta archival memory.")
@@ -40,6 +38,50 @@ def mirror_to_letta(text, target_uri):
     except Exception as e:
         print(f"  Warning: Failed to mirror to Letta: {e}")
 
+def create_annotation(client, target_uri, text, motivation="commenting", quote=None):
+    """Helper function to format and push an at.margin.annotation record."""
+    if target_uri.startswith("at://"):
+        parts = target_uri.replace("at://", "").split("/")
+        if len(parts) >= 3:
+            repo = parts[0]
+            rkey = parts[2]
+            target_uri = f"https://bsky.app/profile/{repo}/post/{rkey}"
+            
+    print(f"  Dispatching annotation to {target_uri}...")
+    
+    try:
+        source_hash = hashlib.sha256(target_uri.encode()).hexdigest()
+        record = {
+            "$type": "at.margin.annotation",
+            "createdAt": client.get_current_time_iso(),
+            "target": {
+                "source": target_uri,
+                "sourceHash": source_hash,
+            },
+            "body": {
+                "value": text
+            },
+            "motivation": motivation
+        }
+        
+        if quote:
+            record["target"]["selector"] = {
+                "type": "TextQuoteSelector",
+                "exact": quote
+            }
+            
+        resp = client.com.atproto.repo.create_record({
+            'repo': client.me.did,
+            'collection': 'at.margin.annotation',
+            'record': record
+        })
+        print(f"  Successfully annotated: {resp.uri}")
+        mirror_to_letta(text, target_uri)
+        return resp.uri
+    except Exception as e:
+        print(f"  Error annotating {target_uri}: {e}", file=sys.stderr)
+        return None
+
 def cmd_sync(args):
     client = get_client()
     agent_id = os.getenv("AGENT_ID", "agent-c52e371d-cb89-4f99-8634-b606bdc69cad")
@@ -134,14 +176,19 @@ def cmd_sync(args):
 #   posts:
 #     - "First post text"
 #     - "Second post text (automatically threads)"
+#   annotation: # Optional: automatically annotates the first post in this block
+#     text: "Internal log message"
+#     motivation: "describing"
 #
 # 2. Reply
 # - action: reply
 #   target_id: "notif_0"  # Resolves from inbox.yaml
 #   posts:
 #     - "My reply text"
+#   annotation: # Optional: automatically annotates your reply
+#     text: "Memory trace"
 #
-# 3. Margin Annotation
+# 3. Margin Annotation (Standalone)
 # - action: annotate
 #   target_id: "notif_1"  # Or explicit at:// URI
 #   text: "My archival observation"
@@ -191,18 +238,24 @@ def cmd_dispatch(args):
             print("Dispatching standalone post/thread...")
             root_ref = None
             parent_ref = None
+            first_post_uri = None
             
             for text in posts:
                 if root_ref is None:
                     post = client.send_post(text=text)
                     root_ref = models.ComAtprotoRepoStrongRef.Main(cid=post.cid, uri=post.uri)
                     parent_ref = root_ref
+                    first_post_uri = post.uri
                 else:
                     reply_ref = models.AppBskyFeedPost.ReplyRef(parent=parent_ref, root=root_ref)
                     post = client.send_post(text=text, reply_to=reply_ref)
                     parent_ref = models.ComAtprotoRepoStrongRef.Main(cid=post.cid, uri=post.uri)
                 print(f"  Posted: {post.uri}")
                 
+            ann = act.get("annotation")
+            if ann and first_post_uri:
+                create_annotation(client, first_post_uri, ann.get("text"), ann.get("motivation", "commenting"), ann.get("quote"))
+                
         elif action_type == "reply":
             target_id = act.get("target_id")
             if target_id not in mapping:
@@ -221,11 +274,18 @@ def cmd_dispatch(args):
                 else:
                     root_ref = parent_ref
                     
+                first_reply_uri = None
                 for text in posts:
                     reply_ref = models.AppBskyFeedPost.ReplyRef(parent=parent_ref, root=root_ref)
                     post = client.send_post(text=text, reply_to=reply_ref)
                     parent_ref = models.ComAtprotoRepoStrongRef.Main(cid=post.cid, uri=post.uri)
                     print(f"  Replied: {post.uri}")
+                    if first_reply_uri is None:
+                        first_reply_uri = post.uri
+                        
+                ann = act.get("annotation")
+                if ann and first_reply_uri:
+                    create_annotation(client, first_reply_uri, ann.get("text"), ann.get("motivation", "commenting"), ann.get("quote"))
                     
             except Exception as e:
                 print(f"Error replying to {target_uri}: {e}")