diff --git a/assets/aws/files/bin/teleport-generate-config b/assets/aws/files/bin/teleport-generate-config
index 644986fadc1..2528ae748c0 100755
--- a/assets/aws/files/bin/teleport-generate-config
+++ b/assets/aws/files/bin/teleport-generate-config
@@ -280,6 +280,11 @@ EOF
         echo "  license_file: /var/lib/teleport/license.pem" >> ${USE_CONFIG_PATH}
     fi
 
+    # configure proxy_listener_mode
+    if [[ -n "${PROXY_MULTIPLEXING}" ]]; then
+        echo "  proxy_listener_mode: ${PROXY_MULTIPLEXING}" >> ${USE_CONFIG_PATH}
+    fi
+
     # enable/start token services and timers
     systemctl_wrap enable teleport-ssm-publish-tokens.service teleport-ssm-publish-tokens.timer
     systemctl_wrap start teleport-ssm-publish-tokens.timer
@@ -479,6 +484,11 @@ EOF
         echo "  license_file: /var/lib/teleport/license.pem" >> ${USE_CONFIG_PATH}
     fi
 
+    # configure proxy_listener_mode
+    if [[ -n "${PROXY_MULTIPLEXING}" ]]; then
+        echo "  proxy_listener_mode: ${PROXY_MULTIPLEXING}" >> ${USE_CONFIG_PATH}
+    fi
+
 cat >>${USE_CONFIG_PATH} <<EOF
 
 ssh_service: