diff --git a/modules/caddyhttp/caddyhttp.go b/modules/caddyhttp/caddyhttp.go
index 6d8e921c0..99bd95222 100644
--- a/modules/caddyhttp/caddyhttp.go
+++ b/modules/caddyhttp/caddyhttp.go
@@ -234,6 +234,8 @@ func (app *App) automaticHTTPS() error {
 
 		// skip if all listeners use the HTTP port
 		if !srv.listenersUseAnyPortOtherThan(app.HTTPPort) {
+			log.Printf("[INFO] Server %v is only listening on the HTTP port %d, so no automatic HTTPS will be applied to this server",
+				srv.Listen, app.HTTPPort)
 			continue
 		}
 
@@ -315,6 +317,12 @@ func (app *App) automaticHTTPS() error {
 
 			log.Printf("[INFO] Enabling automatic HTTP->HTTPS redirects for %v", domains)
 
+			// notify user if their config might override the HTTP->HTTPS redirects
+			if srv.listenersIncludePort(app.HTTPPort) {
+				log.Printf("[WARNING] Server %v is listening on HTTP port %d, so automatic HTTP->HTTPS redirects may be overridden by your own configuration",
+					srv.Listen, app.HTTPPort)
+			}
+
 			// create HTTP->HTTPS redirects
 			for _, addr := range srv.Listen {
 				netw, host, port, err := caddy.SplitListenAddr(addr)
diff --git a/modules/caddyhttp/server.go b/modules/caddyhttp/server.go
index 885ba0b8e..5b651fc25 100644
--- a/modules/caddyhttp/server.go
+++ b/modules/caddyhttp/server.go
@@ -181,6 +181,23 @@ func (s *Server) listenersUseAnyPortOtherThan(otherPort int) bool {
 	return false
 }
 
+// listenersIncludePort returns true if there are any
+// listeners in s that use otherPort.
+func (s *Server) listenersIncludePort(otherPort int) bool {
+	for _, lnAddr := range s.Listen {
+		_, addrs, err := caddy.ParseListenAddr(lnAddr)
+		if err == nil {
+			for _, a := range addrs {
+				_, port, err := net.SplitHostPort(a)
+				if err == nil && port == strconv.Itoa(otherPort) {
+					return true
+				}
+			}
+		}
+	}
+	return false
+}
+
 func (s *Server) hasTLSClientAuth() bool {
 	for _, cp := range s.TLSConnPolicies {
 		if cp.ClientAuthentication != nil && cp.ClientAuthentication.Active() {