diff --git a/t/t0050-filesystem.sh b/t/t0050-filesystem.sh
index ca8568067d31d6..003329c082fae8 100755
--- a/t/t0050-filesystem.sh
+++ b/t/t0050-filesystem.sh
@@ -117,24 +117,4 @@ $test_unicode 'merge (silent unicode normalization)' '
 	git merge topic
 '
 
-test_expect_success CASE_INSENSITIVE_FS 'checkout with no pathspec and a case insensitive fs' '
-	git init repo &&
-	(
-		cd repo &&
-
-		>Gitweb &&
-		git add Gitweb &&
-		git commit -m "add Gitweb" &&
-
-		git checkout --orphan todo &&
-		git reset --hard &&
-		mkdir -p gitweb/subdir &&
-		>gitweb/subdir/file &&
-		git add gitweb &&
-		git commit -m "add gitweb/subdir/file" &&
-
-		git checkout main
-	)
-'
-
 test_done
diff --git a/t/t2021-checkout-overwrite.sh b/t/t2021-checkout-overwrite.sh
index 38c41ae37321ce..729a9bece17208 100755
--- a/t/t2021-checkout-overwrite.sh
+++ b/t/t2021-checkout-overwrite.sh
@@ -79,4 +79,27 @@ test_expect_success 'checkout --overwrite-ignore should succeed if only ignored
 	test_path_is_file some_dir
 '
 
+test_expect_success 'checkout switching to a tracked file replaces a tracked directory' '
+	git init -b main dir-to-file &&
+	(
+		cd dir-to-file &&
+
+		>Gitweb &&
+		git add Gitweb &&
+		git commit -m "add Gitweb" &&
+
+		git checkout --orphan todo &&
+		git reset --hard &&
+		mkdir -p gitweb/subdir &&
+		>gitweb/subdir/file &&
+		git add gitweb &&
+		git commit -m "add gitweb/subdir/file" &&
+
+		git checkout main &&
+
+		test_path_is_file Gitweb &&
+		test_path_is_missing gitweb
+	)
+'
+
 test_done