diff --git a/test/functional/orphaned-renames/test.bats b/test/functional/orphaned-renames/test.bats
index bcc52df..a9beec9 100755
--- a/test/functional/orphaned-renames/test.bats
+++ b/test/functional/orphaned-renames/test.bats
@@ -26,11 +26,25 @@ setup() {
   track_bundle 30 os-core
   track_bundle 30 test-bundle
 
+  set_os_release 40 os-core
+  set_os_release 40 test-bundle
+  track_bundle 40 os-core
+  track_bundle 40 test-bundle
+
+  # /usr/lib/bar and /one will be renamed to /usr/lib/baz and /two
   gen_file_plain_with_content 10 test-bundle /usr/lib/bar "$(seq 100)"
+  gen_file_plain_with_content 10 test-bundle /one "$(printf 'a%.0s' {1..200})"
+
   gen_file_plain_with_content 20 test-bundle /usr/lib/baz "$(seq 100)"
+  gen_file_plain_with_content 20 test-bundle /two "$(printf 'a%.0s' {1..200})"
+
   # different content just to make sure this works with delta renames as well as
   # direct renames
   gen_file_plain_with_content 30 test-bundle /usr/lib/foo "$(seq 100) new"
+
+  gen_file_plain_with_content 40 test-bundle /usr/lib/foo "$(seq 100) new"
+  # new file to force manifest generation
+  gen_file_plain_with_content 40 test-bundle /a "testfile"
 }
 
 @test "create updates with renamed-to file getting deleted" {
@@ -46,16 +60,36 @@ setup() {
 
   sudo $CREATE_UPDATE --osversion 30 --statedir $DIR --format 3
   sudo $MAKE_FULLFILES --statedir $DIR 30
-  # version 10: add file to 10
-  [ 1 -eq $(grep 'F\.\.\.	.*	10	/usr/lib/bar' $DIR/www/10/Manifest.test-bundle | wc -l) ]
-  # version 20: rename bar to baz
-  [ 1 -eq $(grep '\.d\.r	.*	20	/usr/lib/bar' $DIR/www/20/Manifest.test-bundle | wc -l) ]
-  [ 1 -eq $(grep 'F\.\.r	.*	20	/usr/lib/baz' $DIR/www/20/Manifest.test-bundle | wc -l) ]
-  # version 30: prune original renamed-from file (bar), baz is now a renamed-from file
-  # Check for the new renamed-to file (foo)
-  [ 0 -eq $(grep '/usr/lib/bar' $DIR/www/30/Manifest.test-bundle | wc -l) ]
-  [ 1 -eq $(grep '\.d\.r	.*	30	/usr/lib/baz' $DIR/www/30/Manifest.test-bundle | wc -l) ]
-  [ 1 -eq $(grep 'F\.\.r	.*	30	/usr/lib/foo' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+
+  set_latest_ver 30
+
+  sudo $CREATE_UPDATE --osversion 40 --statedir $DIR --format 3
+  sudo $MAKE_FULLFILES --statedir $DIR 40
+  # version 10: add files to 10
+  [ 1 -eq $(grep $'F\.\.\.\t.*\t10\t/usr/lib/bar' $DIR/www/10/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'F\.\.\.\t.*\t10\t/one' $DIR/www/10/Manifest.test-bundle | wc -l) ]
+  # version 20: rename bar to baz and one to two
+  [ 1 -eq $(grep $'\.d\.r\t.*\t20\t/one' $DIR/www/20/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'F\.\.r\t.*\t20\t/two' $DIR/www/20/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.r\t.*\t20\t/usr/lib/bar' $DIR/www/20/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'F\.\.r\t.*\t20\t/usr/lib/baz' $DIR/www/20/Manifest.test-bundle | wc -l) ]
+  # version 30: original renamed-from file (bar) is now orphaned and therefore
+  # deleted, baz is now a renamed-from file and foo is a renamed-to file.
+  # /two was deleted in this version, so both /one and /two should be marked as
+  # deleted
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t20\t/one' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t30\t/two' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t20\t/usr/lib/bar' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.r\t.*\t30\t/usr/lib/baz' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'F\.\.r\t.*\t30\t/usr/lib/foo' $DIR/www/30/Manifest.test-bundle | wc -l) ]
+
+  # version 40: the existing rename from baz -> foo must persist while all
+  # others remain deleted
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t20\t/one' $DIR/www/40/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t30\t/two' $DIR/www/40/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.\.\t0\{64\}\t20\t/usr/lib/bar' $DIR/www/40/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'\.d\.r\t.*\t30\t/usr/lib/baz' $DIR/www/40/Manifest.test-bundle | wc -l) ]
+  [ 1 -eq $(grep $'F\.\.r\t.*\t30\t/usr/lib/foo' $DIR/www/40/Manifest.test-bundle | wc -l) ]
 }
 
 # vi: ft=sh ts=8 sw=2 sts=2 et tw=80