diff --git a/src/checkout.c b/src/checkout.c
index cfb0e72ab..962929075 100644
--- a/src/checkout.c
+++ b/src/checkout.c
@@ -1217,8 +1217,7 @@ static int checkout_update_index(
 
 	memset(&entry, 0, sizeof(entry));
 	entry.path = (char *)file->path; /* cast to prevent warning */
-	git_index_entry__init_from_stat(
-		&entry, st, !(git_index_caps(data->index) & GIT_INDEXCAP_NO_FILEMODE));
+	git_index_entry__init_from_stat(&entry, st, true);
 	git_oid_cpy(&entry.oid, &file->oid);
 
 	return git_index_add(data->index, &entry);
diff --git a/tests/checkout/tree.c b/tests/checkout/tree.c
index f0699fdb7..047c9ed98 100644
--- a/tests/checkout/tree.c
+++ b/tests/checkout/tree.c
@@ -925,3 +925,26 @@ void test_checkout_tree__fails_when_conflicts_exist_in_index(void)
 
 	git_object_free(obj);
 }
+
+void test_checkout_tree__filemode_preserved_in_index(void)
+{
+	git_oid executable_oid;
+	git_commit *commit;
+	git_checkout_opts opts = GIT_CHECKOUT_OPTS_INIT;
+	git_index *index;
+	const git_index_entry *entry;
+
+	cl_git_pass(git_repository_index(&index, g_repo));
+
+	cl_git_pass(git_oid_fromstr(&executable_oid, "afe4393b2b2a965f06acf2ca9658eaa01e0cd6b6"));
+	cl_git_pass(git_commit_lookup(&commit, g_repo, &executable_oid));
+
+	opts.checkout_strategy = GIT_CHECKOUT_FORCE;
+
+	cl_git_pass(git_checkout_tree(g_repo, (const git_object *)commit, &opts));
+	cl_assert(entry = git_index_get_bypath(index, "executable.txt", 0));
+	cl_assert_equal_i(0100755, entry->mode);
+
+	git_commit_free(commit);
+	git_index_free(index);
+}
diff --git a/tests/resources/testrepo/.gitted/objects/1d/d0968be3ff95fcaecb6fa4245662db9fdc4568 b/tests/resources/testrepo/.gitted/objects/1d/d0968be3ff95fcaecb6fa4245662db9fdc4568
new file mode 100644
index 000000000..97c6b2cfa
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diff --git a/tests/resources/testrepo/.gitted/objects/af/e4393b2b2a965f06acf2ca9658eaa01e0cd6b6 b/tests/resources/testrepo/.gitted/objects/af/e4393b2b2a965f06acf2ca9658eaa01e0cd6b6
new file mode 100644
index 000000000..6948f1b1c
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diff --git a/tests/resources/testrepo/.gitted/objects/ce/054d4c5e3c83522aed8bc061987b46b7ede3be b/tests/resources/testrepo/.gitted/objects/ce/054d4c5e3c83522aed8bc061987b46b7ede3be
new file mode 100644
index 000000000..4910e4c0a
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