diff --git a/builtin/checkout.c b/builtin/checkout.c
index 2079aa4170..5ada22a390 100644
--- a/builtin/checkout.c
+++ b/builtin/checkout.c
@@ -863,6 +863,7 @@ static int prepare_linked_checkout(const struct checkout_opts *opts,
 	struct stat st;
 	struct child_process cp;
 	int counter = 0, len, ret;
+	unsigned char rev[20];
 
 	if (!new->commit)
 		die(_("no branch specified"));
@@ -920,13 +921,20 @@ static int prepare_linked_checkout(const struct checkout_opts *opts,
 		   real_path(get_git_common_dir()), name);
 	/*
 	 * This is to keep resolve_ref() happy. We need a valid HEAD
-	 * or is_git_directory() will reject the directory. Any valid
-	 * value would do because this value will be ignored and
-	 * replaced at the next (real) checkout.
+	 * or is_git_directory() will reject the directory. Moreover, HEAD
+	 * in the new worktree must resolve to the same value as HEAD in
+	 * the current tree since the command invoked to populate the new
+	 * worktree will be handed the branch/ref specified by the user.
+	 * For instance, if the user asks for the new worktree to be based
+	 * at HEAD~5, then the resolved HEAD~5 in the new worktree must
+	 * match the resolved HEAD~5 in the current tree in order to match
+	 * the user's expectation.
 	 */
+	if (!resolve_ref_unsafe("HEAD", 0, rev, NULL))
+		die(_("unable to resolve HEAD"));
 	strbuf_reset(&sb);
 	strbuf_addf(&sb, "%s/HEAD", sb_repo.buf);
-	write_file(sb.buf, 1, "%s\n", sha1_to_hex(new->commit->object.sha1));
+	write_file(sb.buf, 1, "%s\n", sha1_to_hex(rev));
 	strbuf_reset(&sb);
 	strbuf_addf(&sb, "%s/commondir", sb_repo.buf);
 	write_file(sb.buf, 1, "../..\n");
diff --git a/t/t2025-checkout-to.sh b/t/t2025-checkout-to.sh
index a8d93366f6..0fd731b4bc 100755
--- a/t/t2025-checkout-to.sh
+++ b/t/t2025-checkout-to.sh
@@ -134,4 +134,14 @@ test_expect_success 'checkout with grafts' '
 	test_cmp expected actual
 '
 
+test_expect_success 'checkout --to from relative HEAD' '
+	test_commit a &&
+	test_commit b &&
+	test_commit c &&
+	git rev-parse HEAD~1 >expected &&
+	git checkout --to relhead HEAD~1 &&
+	git -C relhead rev-parse HEAD >actual &&
+	test_cmp expected actual
+'
+
 test_done