diff --git a/lib/transaction_files.c b/lib/transaction_files.c
index df92fdad..ff865d89 100644
--- a/lib/transaction_files.c
+++ b/lib/transaction_files.c
@@ -443,7 +443,16 @@ collect_file(struct xbps_handle *xhp, const char *file, size_t size,
 		} else if (type == TYPE_DIR && item->old.type == TYPE_DIR) {
 			/*
 			 * Multiple packages removing the same directory.
+			 * Record the last package to remove this directory.
 			 */
+			if (idx < item->old.index || item->old.preserve)
+				return 0;
+			item->old.pkgname = pkgname;
+			item->old.pkgver = pkgver;
+			item->old.index = idx;
+			item->old.preserve = preserve;
+			item->old.update = update;
+			item->old.removepkg = removepkg;
 			return 0;
 		} else {
 			/*
@@ -777,9 +786,9 @@ xbps_transaction_files(struct xbps_handle *xhp, xbps_object_iterator_t iter)
 	while ((obj = xbps_object_iterator_next(iter)) != NULL) {
 		bool update = false;
 		/*
-		 * `idx` is used as package install index, to chose which
-		 * choose the first package which owns or used to own the
-		 * file deletes it.
+		 * `idx` is used as package install index, to choose which
+		 * choose the first or last package which owns or used to
+		 * own the file or directory deletes it.
 		 */
 		idx++;
 
diff --git a/tests/xbps/libxbps/shell/obsoletefiles_test.sh b/tests/xbps/libxbps/shell/obsoletefiles_test.sh
index 27cdd97f..925e63cf 100644
--- a/tests/xbps/libxbps/shell/obsoletefiles_test.sh
+++ b/tests/xbps/libxbps/shell/obsoletefiles_test.sh
@@ -935,6 +935,210 @@ multiple_obsoletes_with_alternatives_unordered_body() {
 	atf_check_equal $? 0
 }
 
+atf_test_case obsolete_directory_multiple_packages1
+
+obsolete_directory_multiple_packages1_head() {
+	atf_set "descr" "Remove multiple packages with the same obsolete directory, variant 1"
+}
+
+obsolete_directory_multiple_packages1_body() {
+	mkdir repo
+	mkdir -p pkg_A/usr/lib/gcc/9.2/include pkg_B/usr/lib/gcc/9.2/include
+	touch pkg_A/usr/lib/gcc/9.2/include/foo.h pkg_B/usr/lib/gcc/9.2/include/bar.h
+
+	cd repo
+	xbps-create -A noarch -n A-1.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-1.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvd A B
+	atf_check_equal $? 0
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	rm -rf pkg_A pkg_B
+	mkdir -p pkg_A/usr/lib/gcc/9.3/include pkg_B/usr/lib/gcc/9.3/include
+	touch pkg_A/usr/lib/gcc/9.3/include/foo.h pkg_B/usr/lib/gcc/9.3/include/bar.h
+
+	cd repo
+	xbps-create -A noarch -n A-2.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-2.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvdu B A
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	ls -lsa root/usr/lib/gcc
+	test -d root/usr/lib/gcc/9.2
+	atf_check_equal $? 1
+}
+
+atf_test_case obsolete_directory_multiple_packages2
+
+obsolete_directory_multiple_packages2_head() {
+	atf_set "descr" "Remove multiple packages with the same obsolete directory, variant 2"
+}
+
+obsolete_directory_multiple_packages2_body() {
+	mkdir repo
+	mkdir -p pkg_A/usr/lib/gcc/9.2/include pkg_B/usr/lib/gcc/9.2/include
+	touch pkg_A/usr/lib/gcc/9.2/include/foo.h pkg_B/usr/lib/gcc/9.2/include/bar.h
+
+	cd repo
+	xbps-create -A noarch -n A-1.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-1.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvd A B
+	atf_check_equal $? 0
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	rm -rf pkg_A pkg_B
+	mkdir -p pkg_A/usr/lib/gcc/9.3/include pkg_B/usr/lib/gcc/9.3/include
+	touch pkg_A/usr/lib/gcc/9.3/include/foo.h pkg_B/usr/lib/gcc/9.3/include/bar.h
+
+	cd repo
+	xbps-create -A noarch -n A-2.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-2.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvdu A B
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	ls -lsa root/usr/lib/gcc
+	test -d root/usr/lib/gcc/9.2
+	atf_check_equal $? 1
+}
+
+atf_test_case obsolete_directory_multiple_packages3
+
+obsolete_directory_multiple_packages3_head() {
+	atf_set "descr" "Remove multiple packages with the same obsolete directory, variant 3"
+}
+
+obsolete_directory_multiple_packages3_body() {
+	mkdir repo
+	mkdir -p pkg_A/usr/lib/gcc/9.2/include pkg_B/usr/lib/gcc/9.2/include pkg_C/usr/lib/gcc/9.2/include
+	touch pkg_A/usr/lib/gcc/9.2/include/foo.h pkg_B/usr/lib/gcc/9.2/include/bar.h pkg_C/usr/lib/gcc/9.2/include/fizz.h
+
+	cd repo
+	xbps-create -A noarch -n A-1.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-1.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-create -A noarch -n C-1.0_1 -s "C pkg" ../pkg_C
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvd A B C
+	atf_check_equal $? 0
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	rm -rf pkg_A pkg_B pkg_C
+	mkdir -p pkg_A/usr/lib/gcc/9.3/include pkg_B/usr/lib/gcc/9.3/include pkg_C/usr/lib/gcc/9.3/include
+	touch pkg_A/usr/lib/gcc/9.3/include/foo.h pkg_B/usr/lib/gcc/9.3/include/bar.h pkg_C/usr/lib/gcc/9.3/include/fizz.h
+
+	cd repo
+	xbps-create -A noarch -n A-2.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-2.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-create -A noarch -n C-2.0_1 -s "C pkg" ../pkg_C
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvdu B A C
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	ls -lsa root/usr/lib/gcc
+	test -d root/usr/lib/gcc/9.2
+	atf_check_equal $? 1
+}
+
+atf_test_case obsolete_directory_multiple_packages4
+
+obsolete_directory_multiple_packages4_head() {
+	atf_set "descr" "Remove multiple packages with the same obsolete directory, variant 4"
+}
+
+obsolete_directory_multiple_packages4_body() {
+	mkdir repo
+	mkdir -p pkg_A/usr/lib/gcc/9.2/include pkg_B/usr/lib/gcc/9.2/include pkg_C/usr/lib/gcc/9.2/include
+	touch pkg_A/usr/lib/gcc/9.2/include/foo.h pkg_B/usr/lib/gcc/9.2/include/bar.h pkg_C/usr/lib/gcc/9.2/include/fizz.h
+
+	cd repo
+	xbps-create -A noarch -n A-1.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-1.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-create -A noarch -n C-1.0_1 -s "C pkg" ../pkg_C
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvd A B C
+	atf_check_equal $? 0
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	rm -rf pkg_A pkg_B pkg_C
+	mkdir -p pkg_A/usr/lib/gcc/9.3/include pkg_B/usr/lib/gcc/9.3/include pkg_C/usr/lib/gcc/9.3/include
+	touch pkg_A/usr/lib/gcc/9.3/include/foo.h pkg_B/usr/lib/gcc/9.3/include/bar.h pkg_C/usr/lib/gcc/9.3/include/fizz.h
+
+	cd repo
+	xbps-create -A noarch -n A-2.0_1 -s "A pkg" ../pkg_A
+	atf_check_equal $? 0
+	xbps-create -A noarch -n B-2.0_1 -s "B pkg" ../pkg_B
+	atf_check_equal $? 0
+	xbps-create -A noarch -n C-2.0_1 -s "C pkg" ../pkg_C
+	atf_check_equal $? 0
+	xbps-rindex -d -a $PWD/*.xbps
+	atf_check_equal $? 0
+	cd ..
+
+	xbps-install -r root --repository=$PWD/repo -yvdu A B C
+
+	xbps-pkgdb -r root -av
+	atf_check_equal $? 0
+
+	ls -lsa root/usr/lib/gcc
+	test -d root/usr/lib/gcc/9.2
+	atf_check_equal $? 1
+}
+
 atf_init_test_cases() {
 	atf_add_test_case reinstall_obsoletes
 	atf_add_test_case root_symlinks_update
@@ -957,4 +1161,8 @@ atf_init_test_cases() {
 	atf_add_test_case obsoletes_with_alternatives
 	atf_add_test_case multiple_obsoletes_with_alternatives
 	atf_add_test_case multiple_obsoletes_with_alternatives_unordered
+	atf_add_test_case obsolete_directory_multiple_packages1
+	atf_add_test_case obsolete_directory_multiple_packages2
+	atf_add_test_case obsolete_directory_multiple_packages3
+	atf_add_test_case obsolete_directory_multiple_packages4
 }