diff --git a/salt/manager/tools/sbin/soup b/salt/manager/tools/sbin/soup
index 276bbc94c..ef1489bf0 100755
--- a/salt/manager/tools/sbin/soup
+++ b/salt/manager/tools/sbin/soup
@@ -1318,6 +1318,8 @@ upgrade_salt() {
     fi
   # Else do Ubuntu things
   elif [[ $is_deb ]]; then
+    # ensure these files don't exist when upgrading from 3006.9 to 3006.16
+    rm -f /etc/apt/keyrings/salt-archive-keyring-2023.pgp /etc/apt/sources.list.d/salt.list
     echo "Removing apt hold for Salt."
     echo ""
     apt-mark unhold "salt-common"