diff --git a/builtin/checkout.c b/builtin/checkout.c
index 23fc56d88d..c93efe4d98 100644
--- a/builtin/checkout.c
+++ b/builtin/checkout.c
@@ -672,10 +672,10 @@ static void suggest_reattach(struct commit *commit, struct rev_info *revs)
  * HEAD.  If it is not reachable from any ref, this is the last chance
  * for the user to do so without resorting to reflog.
  */
-static void orphaned_commit_warning(struct commit *commit)
+static void orphaned_commit_warning(struct commit *old, struct commit *new)
 {
 	struct rev_info revs;
-	struct object *object = &commit->object;
+	struct object *object = &old->object;
 	struct object_array refs;
 
 	init_revisions(&revs, NULL);
@@ -685,16 +685,17 @@ static void orphaned_commit_warning(struct commit *commit)
 	add_pending_object(&revs, object, sha1_to_hex(object->sha1));
 
 	for_each_ref(add_pending_uninteresting_ref, &revs);
+	add_pending_sha1(&revs, "HEAD", new->object.sha1, UNINTERESTING);
 
 	refs = revs.pending;
 	revs.leak_pending = 1;
 
 	if (prepare_revision_walk(&revs))
 		die(_("internal error in revision walk"));
-	if (!(commit->object.flags & UNINTERESTING))
-		suggest_reattach(commit, &revs);
+	if (!(old->object.flags & UNINTERESTING))
+		suggest_reattach(old, &revs);
 	else
-		describe_detached_head(_("Previous HEAD position was"), commit);
+		describe_detached_head(_("Previous HEAD position was"), old);
 
 	clear_commit_marks_for_object_array(&refs, ALL_REV_FLAGS);
 	free(refs.objects);
@@ -731,7 +732,7 @@ static int switch_branches(struct checkout_opts *opts, struct branch_info *new)
 	}
 
 	if (!opts->quiet && !old.path && old.commit && new->commit != old.commit)
-		orphaned_commit_warning(old.commit);
+		orphaned_commit_warning(old.commit, new->commit);
 
 	update_refs_for_switch(opts, &old, new);
 
diff --git a/t/t2020-checkout-detach.sh b/t/t2020-checkout-detach.sh
index b37ce25c42..81005373d7 100755
--- a/t/t2020-checkout-detach.sh
+++ b/t/t2020-checkout-detach.sh
@@ -11,14 +11,13 @@ check_not_detached () {
 	git symbolic-ref -q HEAD >/dev/null
 }
 
-ORPHAN_WARNING='you are leaving .* commit.*behind'
 PREV_HEAD_DESC='Previous HEAD position was'
 check_orphan_warning() {
-	test_i18ngrep "$ORPHAN_WARNING" "$1" &&
+	test_i18ngrep "you are leaving $2 behind" "$1" &&
 	test_i18ngrep ! "$PREV_HEAD_DESC" "$1"
 }
 check_no_orphan_warning() {
-	test_i18ngrep ! "$ORPHAN_WARNING" "$1" &&
+	test_i18ngrep ! "you are leaving .* commit.*behind" "$1" &&
 	test_i18ngrep "$PREV_HEAD_DESC" "$1"
 }
 
@@ -110,12 +109,24 @@ test_expect_success 'checkout warns on orphan commits' '
 	git checkout --detach two &&
 	echo content >orphan &&
 	git add orphan &&
-	git commit -a -m orphan &&
+	git commit -a -m orphan1 &&
+	echo new content >orphan &&
+	git commit -a -m orphan2 &&
+	orphan2=$(git rev-parse HEAD) &&
 	git checkout master 2>stderr
 '
 
 test_expect_success 'checkout warns on orphan commits: output' '
-	check_orphan_warning stderr
+	check_orphan_warning stderr "2 commits"
+'
+
+test_expect_success 'checkout warns orphaning 1 of 2 commits' '
+	git checkout "$orphan2" &&
+	git checkout HEAD^ 2>stderr
+'
+
+test_expect_success 'checkout warns orphaning 1 of 2 commits: output' '
+	check_orphan_warning stderr "1 commit"
 '
 
 test_expect_success 'checkout does not warn leaving ref tip' '