diff --git a/abspath.c b/abspath.c
index 2f0c26e0e2..b02e068aa3 100644
--- a/abspath.c
+++ b/abspath.c
@@ -214,12 +214,12 @@ const char *real_path_if_valid(const char *path)
 	return strbuf_realpath(&realpath, path, 0);
 }
 
-char *real_pathdup(const char *path)
+char *real_pathdup(const char *path, int die_on_error)
 {
 	struct strbuf realpath = STRBUF_INIT;
 	char *retval = NULL;
 
-	if (strbuf_realpath(&realpath, path, 0))
+	if (strbuf_realpath(&realpath, path, die_on_error))
 		retval = strbuf_detach(&realpath, NULL);
 
 	strbuf_release(&realpath);
diff --git a/builtin/init-db.c b/builtin/init-db.c
index 1d4d6a0078..8a6acb0ec6 100644
--- a/builtin/init-db.c
+++ b/builtin/init-db.c
@@ -338,7 +338,7 @@ int init_db(const char *git_dir, const char *real_git_dir,
 {
 	int reinit;
 	int exist_ok = flags & INIT_DB_EXIST_OK;
-	char *original_git_dir = real_pathdup(git_dir);
+	char *original_git_dir = real_pathdup(git_dir, 1);
 
 	if (real_git_dir) {
 		struct stat st;
@@ -489,7 +489,7 @@ int cmd_init_db(int argc, const char **argv, const char *prefix)
 	argc = parse_options(argc, argv, prefix, init_db_options, init_db_usage, 0);
 
 	if (real_git_dir && !is_absolute_path(real_git_dir))
-		real_git_dir = real_pathdup(real_git_dir);
+		real_git_dir = real_pathdup(real_git_dir, 1);
 
 	if (argc == 1) {
 		int mkdir_tried = 0;
@@ -560,7 +560,7 @@ int cmd_init_db(int argc, const char **argv, const char *prefix)
 		const char *git_dir_parent = strrchr(git_dir, '/');
 		if (git_dir_parent) {
 			char *rel = xstrndup(git_dir, git_dir_parent - git_dir);
-			git_work_tree_cfg = real_pathdup(rel);
+			git_work_tree_cfg = real_pathdup(rel, 1);
 			free(rel);
 		}
 		if (!git_work_tree_cfg)
diff --git a/cache.h b/cache.h
index 61fc86e6d7..c26c45f899 100644
--- a/cache.h
+++ b/cache.h
@@ -1109,7 +1109,7 @@ char *strbuf_realpath(struct strbuf *resolved, const char *path,
 		      int die_on_error);
 const char *real_path(const char *path);
 const char *real_path_if_valid(const char *path);
-char *real_pathdup(const char *path);
+char *real_pathdup(const char *path, int die_on_error);
 const char *absolute_path(const char *path);
 char *absolute_pathdup(const char *path);
 const char *remove_leading_path(const char *in, const char *prefix);
diff --git a/dir.c b/dir.c
index 4541f9e146..aeeb5ce104 100644
--- a/dir.c
+++ b/dir.c
@@ -2730,8 +2730,8 @@ void connect_work_tree_and_git_dir(const char *work_tree_, const char *git_dir_)
 {
 	struct strbuf file_name = STRBUF_INIT;
 	struct strbuf rel_path = STRBUF_INIT;
-	char *git_dir = real_pathdup(git_dir_);
-	char *work_tree = real_pathdup(work_tree_);
+	char *git_dir = real_pathdup(git_dir_, 1);
+	char *work_tree = real_pathdup(work_tree_, 1);
 
 	/* Update gitfile */
 	strbuf_addf(&file_name, "%s/.git", work_tree);
diff --git a/environment.c b/environment.c
index c07fb17fb7..42dc3106d2 100644
--- a/environment.c
+++ b/environment.c
@@ -259,7 +259,7 @@ void set_git_work_tree(const char *new_work_tree)
 		return;
 	}
 	git_work_tree_initialized = 1;
-	work_tree = real_pathdup(new_work_tree);
+	work_tree = real_pathdup(new_work_tree, 1);
 }
 
 const char *get_git_work_tree(void)
diff --git a/setup.c b/setup.c
index 967f289f1e..6b48cb91ff 100644
--- a/setup.c
+++ b/setup.c
@@ -698,7 +698,7 @@ static const char *setup_discovered_git_dir(const char *gitdir,
 	/* --work-tree is set without --git-dir; use discovered one */
 	if (getenv(GIT_WORK_TREE_ENVIRONMENT) || git_work_tree_cfg) {
 		if (offset != cwd->len && !is_absolute_path(gitdir))
-			gitdir = real_pathdup(gitdir);
+			gitdir = real_pathdup(gitdir, 1);
 		if (chdir(cwd->buf))
 			die_errno("Could not come back to cwd");
 		return setup_explicit_git_dir(gitdir, cwd, nongit_ok);
@@ -806,7 +806,7 @@ static int canonicalize_ceiling_entry(struct string_list_item *item,
 		/* Keep entry but do not canonicalize it */
 		return 1;
 	} else {
-		char *real_path = real_pathdup(ceil);
+		char *real_path = real_pathdup(ceil, 0);
 		if (!real_path) {
 			return 0;
 		}
diff --git a/submodule.c b/submodule.c
index 3b98766a6b..0a2831d846 100644
--- a/submodule.c
+++ b/submodule.c
@@ -1403,7 +1403,7 @@ static void relocate_single_git_dir_into_superproject(const char *prefix,
 		/* If it is an actual gitfile, it doesn't need migration. */
 		return;
 
-	real_old_git_dir = real_pathdup(old_git_dir);
+	real_old_git_dir = real_pathdup(old_git_dir, 1);
 
 	sub = submodule_from_path(null_sha1, path);
 	if (!sub)
@@ -1412,7 +1412,7 @@ static void relocate_single_git_dir_into_superproject(const char *prefix,
 	new_git_dir = git_path("modules/%s", sub->name);
 	if (safe_create_leading_directories_const(new_git_dir) < 0)
 		die(_("could not create directory '%s'"), new_git_dir);
-	real_new_git_dir = real_pathdup(new_git_dir);
+	real_new_git_dir = real_pathdup(new_git_dir, 1);
 
 	if (!prefix)
 		prefix = get_super_prefix();
@@ -1472,14 +1472,14 @@ void absorb_git_dir_into_superproject(const char *prefix,
 		new_git_dir = git_path("modules/%s", sub->name);
 		if (safe_create_leading_directories_const(new_git_dir) < 0)
 			die(_("could not create directory '%s'"), new_git_dir);
-		real_new_git_dir = real_pathdup(new_git_dir);
+		real_new_git_dir = real_pathdup(new_git_dir, 1);
 		connect_work_tree_and_git_dir(path, real_new_git_dir);
 
 		free(real_new_git_dir);
 	} else {
 		/* Is it already absorbed into the superprojects git dir? */
-		char *real_sub_git_dir = real_pathdup(sub_git_dir);
-		char *real_common_git_dir = real_pathdup(get_git_common_dir());
+		char *real_sub_git_dir = real_pathdup(sub_git_dir, 1);
+		char *real_common_git_dir = real_pathdup(get_git_common_dir(), 1);
 
 		if (!starts_with(real_sub_git_dir, real_common_git_dir))
 			relocate_single_git_dir_into_superproject(prefix, path);
diff --git a/t/t1501-work-tree.sh b/t/t1501-work-tree.sh
index cc5b870e58..b06210ec5e 100755
--- a/t/t1501-work-tree.sh
+++ b/t/t1501-work-tree.sh
@@ -423,4 +423,12 @@ test_expect_success '$GIT_WORK_TREE overrides $GIT_DIR/common' '
 	)
 '
 
+test_expect_success 'error out gracefully on invalid $GIT_WORK_TREE' '
+	(
+		GIT_WORK_TREE=/.invalid/work/tree &&
+		export GIT_WORK_TREE &&
+		test_expect_code 128 git rev-parse
+	)
+'
+
 test_done
diff --git a/transport.c b/transport.c
index d72e089484..b6c5652d6c 100644
--- a/transport.c
+++ b/transport.c
@@ -1221,7 +1221,7 @@ static int refs_from_alternate_cb(struct alternate_object_database *e,
 	const struct ref *extra;
 	struct alternate_refs_data *cb = data;
 
-	other = real_pathdup(e->path);
+	other = real_pathdup(e->path, 1);
 	len = strlen(other);
 
 	while (other[len-1] == '/')
diff --git a/worktree.c b/worktree.c
index d633761575..0486e31ad4 100644
--- a/worktree.c
+++ b/worktree.c
@@ -255,7 +255,7 @@ struct worktree *find_worktree(struct worktree **list,
 		return wt;
 
 	arg = prefix_filename(prefix, strlen(prefix), arg);
-	path = real_pathdup(arg);
+	path = real_pathdup(arg, 1);
 	for (; *list; list++)
 		if (!fspathcmp(path, real_path((*list)->path)))
 			break;