commit - bd4792ec812265a57f6e881d9bff1f297d325749
commit + 21908da4c3cfc3f2d04dd511bd59c1c877f92b14
blob - 70174aa3d9e1dc0477a3ceb497937b6acca741a4
blob + a1d12e6dbe2e63177e9e709a1659d4073b8db842
--- lib/fileindex.c
+++ lib/fileindex.c
@@ -577,8 +577,12 @@ cmp_entries(struct got_fileindex_entry *ie, const char
 
 	if (!in_same_subdir(ie, parent_path, te)) {
 		cmp = strncmp(ie->path, parent_path, parent_len);
-		if (cmp == 0)
-			cmp = strcmp(ie->path + parent_len, te->name);
+		if (cmp == 0) {
+			char *ie_name = ie->path + parent_len;
+			while (ie_name[0] == '/')
+				ie_name++;
+			cmp = strcmp(ie_name, te->name);
+		}
 	} else {
 		char *ie_name = ie->path + parent_len;
 		while (ie_name[0] == '/')
blob - 2438bbf344f4501b2177c6b04e1a90e016407f2f
blob + 62fe285a54aaefa790d4d2c759df4e4733ec5fd0
--- lib/worktree.c
+++ lib/worktree.c
@@ -507,6 +507,27 @@ lock_worktree(struct got_worktree *worktree, int opera
 }
 
 static const struct got_error *
+make_parent_dirs(const char *abspath)
+{
+	const struct got_error *err = NULL;
+
+	char *parent = dirname(abspath);
+	if (parent == NULL)
+		return NULL;
+
+	if (mkdir(parent, GOT_DEFAULT_DIR_MODE) == -1) {
+		if (errno == ENOENT) {
+			err = make_parent_dirs(parent);
+			if (err)
+				return err;
+		} else
+			return got_error_from_errno();
+	}
+
+	return NULL;
+}
+
+static const struct got_error *
 add_dir_on_disk(struct got_worktree *worktree, const char *path)
 {
 	const struct got_error *err = NULL;
@@ -519,20 +540,30 @@ add_dir_on_disk(struct got_worktree *worktree, const c
 	if (mkdir(abspath, GOT_DEFAULT_DIR_MODE) == -1) {
 		struct stat sb;
 
-		if (errno != EEXIST) {
-			err = got_error_from_errno();
-			goto done;
+		if (errno == EEXIST) {
+			if (lstat(abspath, &sb) == -1) {
+				err = got_error_from_errno();
+				goto done;
+			}
+
+			if (!S_ISDIR(sb.st_mode)) {
+				/* TODO directory is obstructed; do something */
+				return got_error(GOT_ERR_FILE_OBSTRUCTED);
+			}
+
+			return NULL;
 		}
 
-		if (lstat(abspath, &sb) == -1) {
+		if (errno == ENOENT) {
+			err = make_parent_dirs(abspath);
+			if (err)
+				return err;
+			if (mkdir(abspath, GOT_DEFAULT_DIR_MODE) == 0)
+				return NULL;
+		} else {
 			err = got_error_from_errno();
 			goto done;
 		}
-
-		if (!S_ISDIR(sb.st_mode)) {
-			/* TODO directory is obstructed; do something */
-			return got_error(GOT_ERR_FILE_OBSTRUCTED);
-		}
 	}
 
 done:
@@ -560,7 +591,19 @@ install_blob(struct got_worktree *worktree, struct got
 	fd = open(ondisk_path, O_RDWR | O_CREAT | O_EXCL | O_NOFOLLOW,
 	    GOT_DEFAULT_FILE_MODE);
 	if (fd == -1) {
-		if (errno == EEXIST) {
+		if (errno == ENOENT) {
+			char *parent = dirname(path);
+			if (parent == NULL)
+				return got_error_from_errno();
+			err = add_dir_on_disk(worktree, parent);
+			if (err)
+				return err;
+			fd = open(ondisk_path,
+			    O_RDWR | O_CREAT | O_EXCL | O_NOFOLLOW,
+			    GOT_DEFAULT_FILE_MODE);
+			if (fd == -1)
+				return got_error_from_errno();
+		} else if (errno == EEXIST) {
 			struct stat sb;
 			if (lstat(ondisk_path, &sb) == -1) {
 				err = got_error_from_errno();
blob - b121574a4f98dd2f74a69c2a49cd1b5f6081c721
blob + 61f3c4d796ad5f9b6b1d8d33f6594411e2d40b22
--- regress/cmdline/update.sh
+++ regress/cmdline/update.sh
@@ -379,9 +379,9 @@ function test_update_moves_files_upwards {
 	(cd $testroot/repo && git mv epsilon/psi/chi/tau epsilon/psi/tau)
 	git_commit $testroot/repo -m "moving files upwards"
 
-	echo "D  epsilon/psi/chi/tau" > $testroot/stdout.expected
+	echo "A  epsilon/mu" > $testroot/stdout.expected
+	echo "D  epsilon/psi/chi/tau" >> $testroot/stdout.expected
 	echo "D  epsilon/psi/mu" >> $testroot/stdout.expected
-	echo "A  epsilon/mu" >> $testroot/stdout.expected
 	echo "A  epsilon/psi/tau" >> $testroot/stdout.expected
 	echo -n "Updated to commit " >> $testroot/stdout.expected
 	git_show_head $testroot/repo >> $testroot/stdout.expected
@@ -569,7 +569,45 @@ function test_update_creates_missing_parent_with_subdi
 
 	test_done "$testroot" "0"
 }
+
+function test_update_file_in_subsubdir {
+	local testroot=`test_init update_fle_in_subsubdir no_tree`
 
+	touch $testroot/repo/Makefile
+	mkdir -p $testroot/repo/altq
+	touch $testroot/repo/altq/if_altq.h
+	mkdir -p $testroot/repo/arch/alpha
+	touch $testroot/repo/arch/alpha/Makefile
+	(cd $testroot/repo && git add .)
+	git_commit $testroot/repo -m "adding initial tree"
+
+	got checkout $testroot/repo $testroot/wt > /dev/null
+	if [ "$?" != "0" ]; then
+		test_done "$testroot" "$?"
+		return 1
+	fi
+
+	echo change > $testroot/repo/arch/alpha/Makefile
+	(cd $testroot/repo && git add .)
+	git_commit $testroot/repo -m "changed a file"
+
+	echo "U  arch/alpha/Makefile" > $testroot/stdout.expected
+	echo -n "Updated to commit " >> $testroot/stdout.expected
+	git_show_head $testroot/repo >> $testroot/stdout.expected
+	echo >> $testroot/stdout.expected
+
+	(cd $testroot/wt && got update > $testroot/stdout)
+
+	cmp $testroot/stdout.expected $testroot/stdout
+	if [ "$?" != "0" ]; then
+		diff -u $testroot/stdout.expected $testroot/stdout
+		test_done "$testroot" "$?"
+		return 1
+	fi
+
+	test_done "$testroot" "0"
+}
+
 run_test test_update_basic
 run_test test_update_adds_file
 run_test test_update_deletes_file
@@ -582,3 +620,4 @@ run_test test_update_moves_files_upwards
 run_test test_update_moves_files_to_new_dir
 run_test test_update_creates_missing_parent
 run_test test_update_creates_missing_parent_with_subdir
+run_test test_update_file_in_subsubdir