1 files changed, 44 insertions, 0 deletions

diff --git a/src/regress/lib/libssl/interop/openssl35/Makefile b/src/regress/lib/libssl/interop/openssl35/Makefile
new file mode 100644
index 0000000000..e11ad5dd20
--- /dev/null
+++ b/src/regress/lib/libssl/interop/openssl35/Makefile
@@ -0,0 +1,44 @@
+# $OpenBSD: Makefile,v 1.1 2025/07/09 17:48:02 tb Exp $
+
+.if ! exists(/usr/local/bin/eopenssl35)
+regress:
+        # install openssl-3.5 from ports for interop tests
+        @echo 'Run "pkg_add openssl--%3.5" to run tests against OpenSSL 3.5'
+        @echo SKIPPED
+.else
+
+PROGS =                 client server
+CFLAGS +=               -DOPENSSL_SUPPRESS_DEPRECATED
+CPPFLAGS =              -I /usr/local/include/eopenssl35
+LDFLAGS =               -L /usr/local/lib/eopenssl35
+LDADD =                 -lssl -lcrypto
+DPADD =                 /usr/local/lib/eopenssl35/libssl.a \
+                        /usr/local/lib/eopenssl35/libcrypto.a
+LD_LIBRARY_PATH =       /usr/local/lib/eopenssl35
+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 $p is linked with OpenSSL 3.5
+        grep -q /usr/local/lib/eopenssl35/libcrypto.so ldd-$p.out
+        grep -q /usr/local/lib/eopenssl35/libssl.so ldd-$p.out
+        # check that $p is not linked with LibreSSL
+        ! grep -v -e libc.so -e libpthread.so ldd-$p.out | grep /usr/lib/
+
+run-version-$p: $p-self.out
+        # check that runtime version is OpenSSL 3.5
+        grep 'SSLEAY_VERSION: OpenSSL 3.5' $p-self.out
+
+run-protocol-$p: $p-self.out
+        # check that OpenSSL 3.5 protocol version is TLS 1.3
+        grep 'Protocol *: TLSv1.3' $p-self.out
+
+.endfor
+
+.endif # exists(/usr/local/bin/eopenssl35)
+
+.include <bsd.regress.mk>