8 files changed, 74 insertions, 11 deletions

diff --git a/src/regress/lib/libssl/interop/Makefile b/src/regress/lib/libssl/interop/Makefile
index 72dc87b5c2..82bef2314d 100644
--- a/src/regress/lib/libssl/interop/Makefile
+++ b/src/regress/lib/libssl/interop/Makefile
@@ -1,6 +1,6 @@
-# $OpenBSD: Makefile,v 1.17 2023/02/01 14:39:09 tb Exp $
+# $OpenBSD: Makefile,v 1.18 2023/10/30 17:15:21 tb Exp $
 
-SUBDIR =        libressl openssl11 openssl30
+SUBDIR =        libressl openssl11 openssl30 openssl31
 
 # the above binaries must have been built before we can continue
 SUBDIR +=       netcat
diff --git a/src/regress/lib/libssl/interop/botan/Makefile b/src/regress/lib/libssl/interop/botan/Makefile
index 23f8a07bf4..b9570b815a 100644
--- a/src/regress/lib/libssl/interop/botan/Makefile
+++ b/src/regress/lib/libssl/interop/botan/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.6 2023/02/01 15:58:20 tb Exp $
+# $OpenBSD: Makefile,v 1.7 2023/10/30 17:15:21 tb Exp $
 
 .include <bsd.own.mk>
 
@@ -26,6 +26,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 LIBRARIES +=            openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+LIBRARIES +=            openssl31
+.endif
 
 PROGS =         client
 SRCS_client =   client.cpp
diff --git a/src/regress/lib/libssl/interop/cert/Makefile b/src/regress/lib/libssl/interop/cert/Makefile
index 47f4422d6e..ae755be223 100644
--- a/src/regress/lib/libssl/interop/cert/Makefile
+++ b/src/regress/lib/libssl/interop/cert/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.10 2023/04/19 15:34:23 tb Exp $
+# $OpenBSD: Makefile,v 1.11 2023/10/30 17:15:21 tb Exp $
 
 # Connect a client to a server.  Both can be current libressl, or
 # openssl 1.1 or 3.0.  Create client and server certificates
@@ -13,6 +13,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 LIBRARIES +=            openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+LIBRARIES +=            openssl31
+.endif
 
 .for cca in noca ca fakeca
 .for sca in noca ca fakeca
diff --git a/src/regress/lib/libssl/interop/cipher/Makefile b/src/regress/lib/libssl/interop/cipher/Makefile
index 85d927a92d..627cfc8f9f 100644
--- a/src/regress/lib/libssl/interop/cipher/Makefile
+++ b/src/regress/lib/libssl/interop/cipher/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.12 2023/04/19 15:34:23 tb Exp $
+# $OpenBSD: Makefile,v 1.13 2023/10/30 17:15:21 tb Exp $
 
 # Connect a client to a server.  Both can be current libressl, or
 # openssl 1.1 or 3.0.  Create lists of supported ciphers
@@ -24,6 +24,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 LIBRARIES +=            openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+LIBRARIES +=            openssl31
+.endif
 
 CLEANFILES =    *.tmp *.ciphers ciphers.mk
 
@@ -53,7 +56,8 @@ client-${clib}-server-${slib}.ciphers: \
         # we are only interested in ciphers supported by libressl
         sort $@ client-libressl.ciphers >$@.tmp
 . if "${clib}" == "openssl11" || "${slib}" == "openssl11" || \
-        "${clib}" == "openssl30" || "${slib}" == "openssl30"
+        "${clib}" == "openssl30" || "${slib}" == "openssl30" || \
+        "${clib}" == "openssl31" || "${slib}" == "openssl31"
         # OpenSSL's SSL_CTX_set_cipher_list doesn't accept TLSv1.3 ciphers
         sed -i '/^TLS_/d' $@.tmp
 . endif
@@ -145,7 +149,7 @@ check-cipher-${cipher}-client-${clib}-server-${slib}: \
 . endif
 . if "${clib}" == "libressl"
         # libressl client may prefer chacha-poly if aes-ni is not supported
-.  if "${slib}" == "openssl11" || "${slib}" == "openssl30"
+.  if "${slib}" == "openssl11" || "${slib}" == "openssl30" || "${slib}" == "openssl31"
         egrep -q ' Cipher *: TLS_(AES_256_GCM_SHA384|CHACHA20_POLY1305_SHA256)$$' ${@:S/^check/server/}.out
 .  else
         egrep -q ' Cipher *: TLS_(AES_256_GCM_SHA384|CHACHA20_POLY1305_SHA256)$$' ${@:S/^check/server/}.out
diff --git a/src/regress/lib/libssl/interop/netcat/Makefile b/src/regress/lib/libssl/interop/netcat/Makefile
index 9cf10417af..568c4d255a 100644
--- a/src/regress/lib/libssl/interop/netcat/Makefile
+++ b/src/regress/lib/libssl/interop/netcat/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.6 2023/02/01 15:38:57 tb Exp $
+# $OpenBSD: Makefile,v 1.7 2023/10/30 17:15:21 tb Exp $
 
 LIBRARIES =             libressl
 .if exists(/usr/local/bin/eopenssl11)
@@ -7,6 +7,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 LIBRARIES +=            openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+LIBRARIES +=            openssl31
+.endif
 
 # run netcat server and connect with test client
 
diff --git a/src/regress/lib/libssl/interop/openssl31/Makefile b/src/regress/lib/libssl/interop/openssl31/Makefile
new file mode 100644
index 0000000000..8f35fa272f
--- /dev/null
+++ b/src/regress/lib/libssl/interop/openssl31/Makefile
@@ -0,0 +1,43 @@
+# $OpenBSD: Makefile,v 1.1 2023/10/30 17:15:21 tb Exp $
+
+.if !exists(/usr/local/bin/eopenssl31)
+regress:
+        # install openssl-3.1 from ports for interop tests
+        @echo 'Run "pkg_add openssl--%3.1" to run tests against OpenSSL 3.1'
+        @echo SKIPPED
+.else
+
+PROGS =                 client server
+CPPFLAGS =              -I /usr/local/include/eopenssl31
+LDFLAGS =               -L /usr/local/lib/eopenssl31
+LDADD =                 -lssl -lcrypto
+DPADD =                 /usr/local/lib/eopenssl31/libssl.a \
+                        /usr/local/lib/eopenssl31/libcrypto.a
+LD_LIBRARY_PATH =       /usr/local/lib/eopenssl31
+REGRESS_TARGETS =       run-self-client-server
+.for p in ${PROGS}
+REGRESS_TARGETS +=      run-ldd-$p run-version-$p run-protocol-$p
+.endfor
+
+.for p in ${PROGS}
+
+run-ldd-$p: ldd-$p.out
+        # check that $p is linked with OpenSSL 3.1
+        grep -q /usr/local/lib/eopenssl31/libcrypto.so ldd-$p.out
+        grep -q /usr/local/lib/eopenssl31/libssl.so ldd-$p.out
+        # check that $p is not linked with LibreSSL
+        ! grep -v libc.so ldd-$p.out | grep /usr/lib/
+
+run-version-$p: $p-self.out
+        # check that runtime version is OpenSSL 3.1
+        grep 'SSLEAY_VERSION: OpenSSL 3.1' $p-self.out
+
+run-protocol-$p: $p-self.out
+        # check that OpenSSL 3.1 protocol version is TLS 1.3
+        grep 'Protocol *: TLSv1.3' $p-self.out
+
+.endfor
+
+.endif # exists(/usr/local/bin/eopenssl31)
+
+.include <bsd.regress.mk>
diff --git a/src/regress/lib/libssl/interop/session/Makefile b/src/regress/lib/libssl/interop/session/Makefile
index f5858eaba0..99daa4ba4f 100644
--- a/src/regress/lib/libssl/interop/session/Makefile
+++ b/src/regress/lib/libssl/interop/session/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.8 2023/02/01 16:03:47 tb Exp $
+# $OpenBSD: Makefile,v 1.9 2023/10/30 17:15:21 tb Exp $
 
 LIBRARIES =             libressl
 .if exists(/usr/local/bin/eopenssl11)
@@ -7,6 +7,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 #LIBRARIES +=           openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+#LIBRARIES +=           openssl31
+.endif
 
 run-session-client-libressl-server-libressl \
 run-session-client-libressl-server-openssl11 \
diff --git a/src/regress/lib/libssl/interop/version/Makefile b/src/regress/lib/libssl/interop/version/Makefile
index c4f7705d63..bb4641afa9 100644
--- a/src/regress/lib/libssl/interop/version/Makefile
+++ b/src/regress/lib/libssl/interop/version/Makefile
@@ -1,4 +1,4 @@
-# $OpenBSD: Makefile,v 1.7 2023/07/02 17:21:32 beck Exp $
+# $OpenBSD: Makefile,v 1.8 2023/10/30 17:15:21 tb Exp $
 
 # Connect a client to a server.  Both can be current libressl, or
 # openssl 1.1 or openssl 3.0.  Pin client or server to a fixed TLS
@@ -13,6 +13,9 @@ LIBRARIES +=		openssl11
 .if exists(/usr/local/bin/eopenssl30)
 LIBRARIES +=            openssl30
 .endif
+.if exists(/usr/local/bin/eopenssl31)
+LIBRARIES +=            openssl31
+.endif
 
 VERSIONS =      any TLS1_2 TLS1_3
 
@@ -29,7 +32,8 @@ FAIL_${cver}_${sver} = !
 .for slib in ${LIBRARIES}
 
 .if ("${cver}" != TLS1_3 && "${sver}" != TLS1_3) && \
-    (("${clib}" != openssl30 && "${slib}" != openssl30) || \
+    ((("${clib}" != openssl30 && "${slib}" != openssl30) && \
+    ("${clib}" != openssl31 && "${slib}" != openssl31)) || \
     (("${cver}" != any && "${sver}" != any) && \
     ("${cver}" != TLS1 && "${sver}" != TLS1) && \
     ("${cver}" != TLS1_1 && "${sver}" != TLS1_1)))