diff --git a/regress/Makefile b/regress/Makefile
index 5caf9b8e4..c21b0215a 100644
--- a/regress/Makefile
+++ b/regress/Makefile
@@ -1,4 +1,4 @@
-#	$OpenBSD: Makefile,v 1.125 2023/05/17 05:52:01 djm Exp $
+#	$OpenBSD: Makefile,v 1.126 2023/09/06 23:36:09 djm Exp $
 
 tests:		prep file-tests t-exec unit
 
@@ -103,7 +103,8 @@ LTESTS= 	connect \
 		agent-restrict \
 		hostbased \
 		channel-timeout \
-		connection-timeout
+		connection-timeout \
+		match-subsystem
 
 INTEROP_TESTS=	putty-transfer putty-ciphers putty-kex conch-ciphers
 #INTEROP_TESTS+=ssh-com ssh-com-client ssh-com-keygen ssh-com-sftp
diff --git a/regress/match-subsystem.sh b/regress/match-subsystem.sh
new file mode 100644
index 000000000..0b691d8e8
--- /dev/null
+++ b/regress/match-subsystem.sh
@@ -0,0 +1,90 @@
+#	$OpenBSD: match-subsystem.sh,v 1.1 2023/09/06 23:36:09 djm Exp $
+#	Placed in the Public Domain.
+
+tid="sshd_config match subsystem"
+
+cp $OBJ/sshd_proxy $OBJ/sshd_proxy_bak
+
+try_subsystem() {
+	_id=$1
+	_subsystem=$2
+	_expect=$3
+	${SSHD} -tf $OBJ/sshd_proxy || fatal "$_id: bad config"
+	${SSH} -sF $OBJ/ssh_proxy somehost $_subsystem
+	_exit=$?
+	trace "$_id subsystem $_subsystem"
+	if [ $_exit -ne $_expect ] ; then
+		fail "$_id: subsystem $_subsystem exit $_exit expected $_expect"
+	fi
+	return $?
+}
+
+# Simple case: subsystem in main config.
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Subsystem xxx /bin/sh -c "exit 23"
+_EOF
+try_subsystem "main config" xxx 23
+
+# No clobber in main config.
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Subsystem xxx /bin/sh -c "exit 23"
+Subsystem xxx /bin/sh -c "exit 24"
+_EOF
+try_subsystem "main config no clobber" xxx 23
+
+# Subsystem in match all block
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Match all
+Subsystem xxx /bin/sh -c "exit 21"
+_EOF
+try_subsystem "match all" xxx 21
+
+# No clobber in match all block
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Match all
+Subsystem xxx /bin/sh -c "exit 21"
+Subsystem xxx /bin/sh -c "exit 24"
+_EOF
+try_subsystem "match all no clobber" xxx 21
+
+# Subsystem in match user block
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Match user *
+Subsystem xxx /bin/sh -c "exit 20"
+_EOF
+try_subsystem "match user" xxx 20
+
+# No clobber in match user block
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Match user *
+Subsystem xxx /bin/sh -c "exit 20"
+Subsystem xxx /bin/sh -c "exit 24"
+Match all
+Subsystem xxx /bin/sh -c "exit 24"
+_EOF
+try_subsystem "match user no clobber" xxx 20
+
+# Override main with match all
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Subsystem xxx /bin/sh -c "exit 23"
+Match all
+Subsystem xxx /bin/sh -c "exit 19"
+_EOF
+try_subsystem "match all override" xxx 19
+
+# Override main with match user
+cp $OBJ/sshd_proxy_bak $OBJ/sshd_proxy
+cat >> $OBJ/sshd_proxy << _EOF
+Subsystem xxx /bin/sh -c "exit 23"
+Match user *
+Subsystem xxx /bin/sh -c "exit 18"
+_EOF
+try_subsystem "match user override" xxx 18
+