diff --git a/cache.h b/cache.h
index 6fda8091f1..4f0b29bfe4 100644
--- a/cache.h
+++ b/cache.h
@@ -1659,7 +1659,7 @@ static inline void cache_def_clear(struct cache_def *cache)
 
 int has_symlink_leading_path(const char *name, int len);
 int threaded_has_symlink_leading_path(struct cache_def *, const char *, int);
-int check_leading_path(const char *name, int len);
+int check_leading_path(const char *name, int len, int warn_on_lstat_err);
 int has_dirs_only_path(const char *name, int len, int prefix_len);
 void invalidate_lstat_cache(void);
 void schedule_dir_for_removal(const char *name, int len);
diff --git a/entry.c b/entry.c
index 7b9f43716f..33ce80ca91 100644
--- a/entry.c
+++ b/entry.c
@@ -530,7 +530,7 @@ void unlink_entry(const struct cache_entry *ce)
 		submodule_move_head(ce->name, "HEAD", NULL,
 				    SUBMODULE_MOVE_HEAD_FORCE);
 	}
-	if (!check_leading_path(ce->name, ce_namelen(ce)))
+	if (check_leading_path(ce->name, ce_namelen(ce), 1) >= 0)
 		return;
 	if (remove_or_warn(ce->ce_mode, ce->name))
 		return;
diff --git a/symlinks.c b/symlinks.c
index 7dbb6b23d9..5232d02020 100644
--- a/symlinks.c
+++ b/symlinks.c
@@ -1,6 +1,7 @@
 #include "cache.h"
 
-static int threaded_check_leading_path(struct cache_def *cache, const char *name, int len);
+static int threaded_check_leading_path(struct cache_def *cache, const char *name,
+				       int len, int warn_on_lstat_err);
 static int threaded_has_dirs_only_path(struct cache_def *cache, const char *name, int len, int prefix_len);
 
 /*
@@ -72,7 +73,7 @@ static int lstat_cache_matchlen(struct cache_def *cache,
 				int prefix_len_stat_func)
 {
 	int match_len, last_slash, last_slash_dir, previous_slash;
-	int save_flags, ret;
+	int save_flags, ret, saved_errno = 0;
 	struct stat st;
 
 	if (cache->track_flags != track_flags ||
@@ -139,6 +140,7 @@ static int lstat_cache_matchlen(struct cache_def *cache,
 
 		if (ret) {
 			*ret_flags = FL_LSTATERR;
+			saved_errno = errno;
 			if (errno == ENOENT)
 				*ret_flags |= FL_NOENT;
 		} else if (S_ISDIR(st.st_mode)) {
@@ -180,6 +182,8 @@ static int lstat_cache_matchlen(struct cache_def *cache,
 	} else {
 		reset_lstat_cache(cache);
 	}
+	if (saved_errno)
+		errno = saved_errno;
 	return match_len;
 }
 
@@ -202,57 +206,47 @@ int threaded_has_symlink_leading_path(struct cache_def *cache, const char *name,
 	return lstat_cache(cache, name, len, FL_SYMLINK|FL_DIR, USE_ONLY_LSTAT) & FL_SYMLINK;
 }
 
-/*
- * Return non-zero if path 'name' has a leading symlink component
- */
 int has_symlink_leading_path(const char *name, int len)
 {
 	return threaded_has_symlink_leading_path(&default_cache, name, len);
 }
 
-/*
- * Return zero if path 'name' has a leading symlink component or
- * if some leading path component does not exists.
- *
- * Return -1 if leading path exists and is a directory.
- *
- * Return path length if leading path exists and is neither a
- * directory nor a symlink.
- */
-int check_leading_path(const char *name, int len)
+int check_leading_path(const char *name, int len, int warn_on_lstat_err)
 {
-	return threaded_check_leading_path(&default_cache, name, len);
+	return threaded_check_leading_path(&default_cache, name, len,
+					   warn_on_lstat_err);
 }
 
 /*
- * Return zero if path 'name' has a leading symlink component or
- * if some leading path component does not exists.
+ * Return zero if some leading path component of 'name' does not exist.
  *
  * Return -1 if leading path exists and is a directory.
  *
- * Return path length if leading path exists and is neither a
- * directory nor a symlink.
+ * Return the length of a leading component if it either exists but it's not a
+ * directory, or if we were unable to lstat() it. If warn_on_lstat_err is true,
+ * also emit a warning for this error.
  */
-static int threaded_check_leading_path(struct cache_def *cache, const char *name, int len)
+static int threaded_check_leading_path(struct cache_def *cache, const char *name,
+				       int len, int warn_on_lstat_err)
 {
 	int flags;
 	int match_len = lstat_cache_matchlen(cache, name, len, &flags,
 			   FL_SYMLINK|FL_NOENT|FL_DIR, USE_ONLY_LSTAT);
+	int saved_errno = errno;
+
 	if (flags & FL_NOENT)
 		return 0;
 	else if (flags & FL_DIR)
 		return -1;
-	else
-		return match_len;
+	if (warn_on_lstat_err && (flags & FL_LSTATERR)) {
+		char *path = xmemdupz(name, match_len);
+		errno = saved_errno;
+		warning_errno(_("failed to lstat '%s'"), path);
+		free(path);
+	}
+	return match_len;
 }
 
-/*
- * Return non-zero if all path components of 'name' exists as a
- * directory.  If prefix_len > 0, we will test with the stat()
- * function instead of the lstat() function for a prefix length of
- * 'prefix_len', thus we then allow for symlinks in the prefix part as
- * long as those points to real existing directories.
- */
 int has_dirs_only_path(const char *name, int len, int prefix_len)
 {
 	return threaded_has_dirs_only_path(&default_cache, name, len, prefix_len);
diff --git a/t/t2021-checkout-overwrite.sh b/t/t2021-checkout-overwrite.sh
index c2ada7de37..70d69263e6 100755
--- a/t/t2021-checkout-overwrite.sh
+++ b/t/t2021-checkout-overwrite.sh
@@ -51,4 +51,16 @@ test_expect_success SYMLINKS 'the symlink remained' '
 	test -h a/b
 '
 
+test_expect_success SYMLINKS 'checkout -f must not follow symlinks when removing entries' '
+	git checkout -f start &&
+	mkdir dir &&
+	>dir/f &&
+	git add dir/f &&
+	git commit -m "add dir/f" &&
+	mv dir untracked &&
+	ln -s untracked dir &&
+	git checkout -f HEAD~ &&
+	test_path_is_file untracked/f
+'
+
 test_done
diff --git a/unpack-trees.c b/unpack-trees.c
index 9af8e796b3..29029f34ed 100644
--- a/unpack-trees.c
+++ b/unpack-trees.c
@@ -2097,7 +2097,7 @@ static int verify_absent_1(const struct cache_entry *ce,
 	if (o->index_only || o->reset || !o->update)
 		return 0;
 
-	len = check_leading_path(ce->name, ce_namelen(ce));
+	len = check_leading_path(ce->name, ce_namelen(ce), 0);
 	if (!len)
 		return 0;
 	else if (len > 0) {