diff --git a/scripts/workers/services/sc_coc_filing.py b/scripts/workers/services/sc_coc_filing.py
index 203a1bb..fb5116b 100644
--- a/scripts/workers/services/sc_coc_filing.py
+++ b/scripts/workers/services/sc_coc_filing.py
@@ -44,6 +44,8 @@ SMTP_USER = os.getenv("SMTP_USER", "")
 SMTP_PASS = os.getenv("SMTP_PASS", "")
 SMTP_FROM = os.getenv("SMTP_FROM", "Performance West <noreply@performancewest.net>")
 FROM_ADDR = "noreply@performancewest.net"
+# Replies (carrier questions) route to the monitored info@ mailbox.
+REPLY_TO = os.getenv("SC_COC_REPLY_TO", "info@performancewest.net")
 
 # SCDMV COC submission coordinates (from SCDMV Form COC, rev 11/2025).
 SCDMV_COC = {
@@ -90,6 +92,9 @@ def send_insurance_question_email(order_number: str, customer_email: str,
         f"intrastate operation?\n\n"
         f"(Note: this must be a Form E filed by your insurance COMPANY directly "
         f"with SCDMV — a regular ACORD certificate of insurance is not accepted.)\n\n"
+        f"Not sure? Give your insurance agent a quick call and ask if they can "
+        f"file a Form E with the SCDMV before choosing below — that way we pick "
+        f"the right next step the first time.\n\n"
         f"✅ YES — my insurer can file the Form E:\n{yes_url}\n\n"
         f"❌ NO / NOT SURE — I need help getting the right insurance:\n{no_url}\n\n"
         f"If you click NO, no problem — we'll connect you with a broker who writes "
@@ -105,6 +110,7 @@ def send_insurance_question_email(order_number: str, customer_email: str,
         msg["Subject"] = f"Quick question about your SC insurance — {entity_name}"
         msg["From"] = SMTP_FROM
         msg["To"] = customer_email
+        msg["Reply-To"] = REPLY_TO
         with smtplib.SMTP(SMTP_HOST, SMTP_PORT, timeout=30) as s:
             s.starttls()
             if SMTP_USER and SMTP_PASS: