diff --git a/lib/libcrypto/x509/x509_constraints.c b/lib/libcrypto/x509/x509_constraints.c
index 0773d2ba719..c4f32c9cfc7 100644
--- a/lib/libcrypto/x509/x509_constraints.c
+++ b/lib/libcrypto/x509/x509_constraints.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: x509_constraints.c,v 1.32 2023/09/29 15:53:59 beck Exp $ */
+/* $OpenBSD: x509_constraints.c,v 1.33 2026/04/13 17:04:23 beck Exp $ */
 /*
  * Copyright (c) 2020 Bob Beck <beck@openbsd.org>
  *
@@ -578,11 +578,30 @@ x509_constraints_sandns(char *sandns, size_t dlen, char *constraint, size_t len)
 	if (len == 0)
 		return 1; /* an empty constraint matches everything */
 
-	/* match the end of the domain */
 	if (dlen < len)
 		return 0;
-	suffix = sandns + (dlen - len);
-	return (strncasecmp(suffix, constraint, len) == 0);
+
+	if (dlen == len)
+		return (strncasecmp(sandns, constraint, len) == 0);
+
+	/* Support a constraint with a leading "." */
+	if (constraint[0] == '.') {
+		constraint++;
+		len--;
+	}
+
+	/*
+	 * Otherwise we must have at least one extra component
+	 * to match, so there must be more than just a leading .
+	 */
+	if (dlen - len > 1) {
+		suffix = sandns + (dlen - len);
+		if (suffix[-1] != '.')
+			return 0;
+		return (strncasecmp(suffix, constraint, len) == 0);
+	}
+
+	return 0;
 }
 
 /*
diff --git a/lib/libcrypto/x509/x509_internal.h b/lib/libcrypto/x509/x509_internal.h
index 9b9980ece57..e933cd9f2d1 100644
--- a/lib/libcrypto/x509/x509_internal.h
+++ b/lib/libcrypto/x509/x509_internal.h
@@ -1,4 +1,4 @@
-/* $OpenBSD: x509_internal.h,v 1.28 2024/05/19 07:12:50 jsg Exp $ */
+/* $OpenBSD: x509_internal.h,v 1.29 2026/04/13 17:04:23 beck Exp $ */
 /*
  * Copyright (c) 2020 Bob Beck <beck@openbsd.org>
  *
@@ -116,6 +116,8 @@ int x509_constraints_valid_host(CBS *cbs, int permit_ip);
 int x509_constraints_valid_sandns(CBS *cbs);
 int x509_constraints_domain(char *domain, size_t dlen, char *constraint,
     size_t len);
+int x509_constraints_sandns(char *domain, size_t dlen, char *constraint,
+    size_t len);
 int x509_constraints_parse_mailbox(CBS *candidate,
     struct x509_constraints_name *name);
 int x509_constraints_valid_domain_constraint(CBS *cbs);
diff --git a/regress/lib/libcrypto/x509/constraints.c b/regress/lib/libcrypto/x509/constraints.c
index 16e135bb44c..54bb654a31b 100644
--- a/regress/lib/libcrypto/x509/constraints.c
+++ b/regress/lib/libcrypto/x509/constraints.c
@@ -1,4 +1,4 @@
-/*	$OpenBSD: constraints.c,v 1.18 2023/12/13 05:59:50 tb Exp $	*/
+/*	$OpenBSD: constraints.c,v 1.19 2026/04/13 17:04:23 beck Exp $	*/
 /*
  * Copyright (c) 2020 Bob Beck <beck@openbsd.org>
  *
@@ -558,7 +558,54 @@ test_constraints1(void)
 		failure = 1;
 		goto done;
 	}
-
+	c = "openbsd.org";
+	cl = strlen("openbsd.org");
+	d = "oopenbsd.org";
+	dl = strlen("oopenbsd.org");
+	if (x509_constraints_sandns(d, dl, c, cl)) {
+		FAIL("constraint '%s' should not have matched '%s'\n",
+		    c, d);
+		failure = 1;
+		goto done;
+	}
+	d = "*.openbsd.org";
+	dl = strlen("*.openbsd.org");
+	if (!x509_constraints_sandns(d, dl, c, cl)) {
+		FAIL("constraint '%s' should have matched '%s'\n",
+		    c, d);
+		failure = 1;
+		goto done;
+	}
+	c = "www.openbsd.org";
+	cl = strlen("www.openbsd.org");
+	if (x509_constraints_sandns(d, dl, c, cl)) {
+		FAIL("constraint '%s' should not have matched '%s'\n",
+		    c, d);
+		failure = 1;
+		goto done;
+	}
+	c = "";
+	cl = 0;
+	if (!x509_constraints_sandns(d, dl, c, cl)) {
+		FAIL("constraint '%s' should have matched '%s'\n",
+		    c, d);
+		failure = 1;
+		goto done;
+	}
+	/*
+	 * Note that this *will* match, but we do not allow ".openbsd.org"
+	 * as a sandns name - see invalid sandnsname tests above.
+	 */
+	c = ".openbsd.org";
+	cl = strlen(".openbsd.org");
+	d = ".openbsd.org";
+	dl = strlen(".openbsd.org");
+	if (!x509_constraints_sandns(d, dl, c, cl)) {
+		FAIL("constraint '%s' should have matched '%s'\n",
+		    c, d);
+		failure = 1;
+		goto done;
+	}
  done:
 	return failure;
 }