diff --git a/builtin/ls-files.c b/builtin/ls-files.c
index b148607f7a..09d95111b3 100644
--- a/builtin/ls-files.c
+++ b/builtin/ls-files.c
@@ -703,7 +703,7 @@ int cmd_ls_files(int argc,
 	if (dir.exclude_per_dir)
 		exc_given = 1;
 
-	if (require_work_tree && !is_inside_work_tree())
+	if (require_work_tree && !is_inside_work_tree(repo))
 		setup_work_tree();
 
 	if (recurse_submodules &&
diff --git a/builtin/rev-parse.c b/builtin/rev-parse.c
index a216be63cf..2fcd6851d1 100644
--- a/builtin/rev-parse.c
+++ b/builtin/rev-parse.c
@@ -1006,7 +1006,7 @@ int cmd_rev_parse(int argc,
 			}
 			if (!strcmp(arg, "--show-cdup")) {
 				const char *pfx = prefix;
-				if (!is_inside_work_tree()) {
+				if (!is_inside_work_tree(the_repository)) {
 					const char *work_tree =
 						repo_get_work_tree(the_repository);
 					if (work_tree)
@@ -1068,7 +1068,7 @@ int cmd_rev_parse(int argc,
 				continue;
 			}
 			if (!strcmp(arg, "--is-inside-work-tree")) {
-				printf("%s\n", is_inside_work_tree() ? "true"
+				printf("%s\n", is_inside_work_tree(the_repository) ? "true"
 						: "false");
 				continue;
 			}
diff --git a/object-name.c b/object-name.c
index 21dcdc4a0e..37a9ce8e87 100644
--- a/object-name.c
+++ b/object-name.c
@@ -1703,7 +1703,7 @@ static char *resolve_relative_path(struct repository *r, const char *rel)
 	if (!starts_with(rel, "./") && !starts_with(rel, "../"))
 		return NULL;
 
-	if (r != the_repository || !is_inside_work_tree())
+	if (r != the_repository || !is_inside_work_tree(the_repository))
 		die(_("relative path syntax can't be used outside working tree"));
 
 	/* die() inside prefix_path() if resolved path is outside worktree */
diff --git a/setup.c b/setup.c
index 80f3ba0d62..041e08b98d 100644
--- a/setup.c
+++ b/setup.c
@@ -26,7 +26,6 @@
 #include "trace2.h"
 #include "worktree.h"
 
-static int inside_work_tree = -1;
 static int work_tree_config_is_bogus;
 enum allowed_bare_repo {
 	ALLOWED_BARE_REPO_EXPLICIT = 0,
@@ -298,7 +297,7 @@ void verify_filename(const char *prefix,
  */
 void verify_non_filename(const char *prefix, const char *arg)
 {
-	if (!is_inside_work_tree() || is_inside_git_dir(the_repository))
+	if (!is_inside_work_tree(the_repository) || is_inside_git_dir(the_repository))
 		return;
 	if (*arg == '-')
 		return; /* flag */
@@ -477,11 +476,20 @@ int is_inside_git_dir(struct repository *repo)
 	return ret;
 }
 
-int is_inside_work_tree(void)
+int is_inside_work_tree(struct repository *repo)
 {
-	if (inside_work_tree < 0)
-		inside_work_tree = is_inside_dir(repo_get_work_tree(the_repository));
-	return inside_work_tree;
+	struct strbuf buf = STRBUF_INIT;
+	const char *worktree;
+	int ret;
+
+	worktree = repo_get_work_tree(repo);
+	if (!worktree)
+		return 0;
+
+	ret = is_inside_dir(strbuf_realpath(&buf, worktree, 1));
+
+	strbuf_release(&buf);
+	return ret;
 }
 
 void setup_work_tree(void)
@@ -798,13 +806,10 @@ static int check_repository_format_gently(struct repository *repo,
 	if (!has_common) {
 		if (candidate->is_bare != -1) {
 			is_bare_repository_cfg = candidate->is_bare;
-			if (is_bare_repository_cfg == 1)
-				inside_work_tree = -1;
 		}
 		if (candidate->work_tree) {
 			free(git_work_tree_cfg);
 			git_work_tree_cfg = xstrdup(candidate->work_tree);
-			inside_work_tree = -1;
 		}
 	}
 
@@ -1251,7 +1256,6 @@ static const char *setup_discovered_git_dir(struct repository *repo,
 	set_git_work_tree(".");
 	if (strcmp(gitdir, DEFAULT_GIT_DIR_ENVIRONMENT))
 		set_git_dir(repo, gitdir, 0);
-	inside_work_tree = 1;
 	if (offset >= cwd->len)
 		return NULL;
 
@@ -1286,7 +1290,6 @@ static const char *setup_bare_git_dir(struct repository *repo,
 		return setup_explicit_git_dir(repo, gitdir, cwd, repo_fmt, nongit_ok);
 	}
 
-	inside_work_tree = 0;
 	if (offset != cwd->len) {
 		if (chdir(cwd->buf))
 			die_errno(_("cannot come back to cwd"));
diff --git a/setup.h b/setup.h
index 115bda647c..71d3f91883 100644
--- a/setup.h
+++ b/setup.h
@@ -5,7 +5,7 @@
 #include "string-list.h"
 
 int is_inside_git_dir(struct repository *repo);
-int is_inside_work_tree(void);
+int is_inside_work_tree(struct repository *repo);
 int get_common_dir_noenv(struct strbuf *sb, const char *gitdir);
 int get_common_dir(struct strbuf *sb, const char *gitdir);
 
diff --git a/submodule.c b/submodule.c
index b1a0363f9d..a939ff5072 100644
--- a/submodule.c
+++ b/submodule.c
@@ -2620,7 +2620,7 @@ int get_superproject_working_tree(struct strbuf *buf)
 	int code;
 	ssize_t len;
 
-	if (!is_inside_work_tree())
+	if (!is_inside_work_tree(the_repository))
 		/*
 		 * FIXME:
 		 * We might have a superproject, but it is harder