diff --git a/goodnews/api.py b/goodnews/api.py
index 5e79ebb..72d9f21 100644
--- a/goodnews/api.py
+++ b/goodnews/api.py
@@ -845,6 +845,8 @@ def create_app() -> FastAPI:
         message = (body.message or "").strip()[:4000]
         if not message:
             raise HTTPException(status_code=422, detail="Reply message is required.")
+        # 1. Validate + gather, then release the DB connection — SMTP can take
+        #    ~20s and shouldn't keep a connection open.
         with get_conn() as conn:
             admin = _require_admin(conn, request)
             fb = conn.execute("SELECT contact_email, message FROM feedback WHERE id = ?", (fid,)).fetchone()
@@ -852,15 +854,18 @@ def create_app() -> FastAPI:
                 raise HTTPException(status_code=404, detail="feedback not found")
             if not fb["contact_email"]:
                 raise HTTPException(status_code=400, detail="No reply address for this feedback.")
-            # Send first — only record a reply that actually went out, so the UI
-            # can keep the draft on failure.
-            try:
-                email_send.send_feedback_reply(fb["contact_email"], message, fb["message"])
-            except Exception as exc:  # noqa: BLE001 — surface any SMTP failure to the admin
-                raise HTTPException(status_code=502, detail=f"Could not send the reply: {exc}")
+            admin_id, to, original = admin["id"], fb["contact_email"], fb["message"]
+        # 2. Send with no DB connection held; only record a reply that actually
+        #    went out, so the UI can keep the draft on failure.
+        try:
+            email_send.send_feedback_reply(to, message, original)
+        except Exception as exc:  # noqa: BLE001 — surface any SMTP failure to the admin
+            raise HTTPException(status_code=502, detail=f"Could not send the reply: {exc}")
+        # 3. Record the sent reply + mark the item read.
+        with get_conn() as conn:
             cur = conn.execute(
                 "INSERT INTO feedback_replies (feedback_id, user_id, message, sent_to) VALUES (?, ?, ?, ?)",
-                (fid, admin["id"], message, fb["contact_email"]),
+                (fid, admin_id, message, to),
             )
             conn.execute(
                 "UPDATE feedback SET read_at = COALESCE(read_at, CURRENT_TIMESTAMP) WHERE id = ?", (fid,)