Re: [PATCH] test/ssl: rework the sslfiles Makefile target

Jacob Champion Tue, 29 Jun 2021 13:14:33 -0700

On Thu, 2021-03-04 at 00:03 +0000, Jacob Champion wrote:
> Hello all,
> 
> Andrew pointed out elsewhere [1] that it's pretty difficult to add new
> certificates to the test/ssl suite without blowing away the current
> state and starting over. I needed new cases for the NSS backend work,
> and ran into the same pain, so here is my attempt to improve the
> situation.


v2 is a rebase to resolve conflicts around SSL compression and the new
client-dn test case.

--Jacob

From bf1c350008ad49ba0e343c3e1d50a8cf1ff368d0 Mon Sep 17 00:00:00 2001
From: Jacob Champion <pchamp...@vmware.com>
Date: Fri, 26 Feb 2021 15:25:28 -0800
Subject: [PATCH v2] test/ssl: rework the sslfiles Makefile target

Adding a new certificate is as easy as dropping in a new .config file,
adding it to the top of the Makefile, and running `make sslfiles`.

Improvements:
- Interfile dependencies should be fixed, with the exception of the CRL
  dirs.
- New certificates have serial numbers based on the current time,
  reducing the chance of collision.
- The CA index state is created on demand and cleaned up automatically
  at the end of the Make run.
- *.config files are now self-contained; one certificate needs one
  config file instead of two.
- Duplication is reduced, and along with it some unneeded code (and
  possible copy-paste errors), such as the unused server-ss cert.
---
 src/Makefile.global.in                        |   5 +-
 src/test/ssl/Makefile                         | 261 ++++++++++--------
 src/test/ssl/README                           |   3 -
 src/test/ssl/cas.config                       |  10 +-
 src/test/ssl/client-dn.config                 |   1 -
 src/test/ssl/client-revoked.config            |  13 +
 src/test/ssl/client.config                    |   1 -
 src/test/ssl/client_ca.config                 |   5 +
 src/test/ssl/root_ca.config                   |   1 +
 src/test/ssl/server-cn-only.config            |   3 +-
 src/test/ssl/server-no-names.config           |   5 +-
 src/test/ssl/server-revoked.config            |   3 +-
 src/test/ssl/server_ca.config                 |   5 +
 src/test/ssl/ssl/both-cas-1.crt               |  86 +++---
 src/test/ssl/ssl/both-cas-2.crt               |  86 +++---
 src/test/ssl/ssl/client+client_ca.crt         |  65 ++---
 src/test/ssl/ssl/client-crldir/9bb9e3c3.r0    |  18 +-
 src/test/ssl/ssl/client-dn.crt                |  34 +--
 src/test/ssl/ssl/client-revoked.crt           |  31 ++-
 src/test/ssl/ssl/client.crl                   |  18 +-
 src/test/ssl/ssl/client.crt                   |  31 ++-
 src/test/ssl/ssl/client_ca.crt                |  34 +--
 .../ssl/ssl/root+client-crldir/9bb9e3c3.r0    |  18 +-
 .../ssl/ssl/root+client-crldir/a3d11bff.r0    |  16 +-
 src/test/ssl/ssl/root+client.crl              |  34 +--
 src/test/ssl/ssl/root+client_ca.crt           |  52 ++--
 .../ssl/ssl/root+server-crldir/a3d11bff.r0    |  16 +-
 .../ssl/ssl/root+server-crldir/a836cc2d.r0    |  18 +-
 src/test/ssl/ssl/root+server.crl              |  34 +--
 src/test/ssl/ssl/root+server_ca.crt           |  52 ++--
 src/test/ssl/ssl/root.crl                     |  16 +-
 src/test/ssl/ssl/root_ca.crt                  |  18 +-
 src/test/ssl/ssl/server-cn-and-alt-names.crt  |  36 +--
 src/test/ssl/ssl/server-cn-only.crt           |  33 +--
 src/test/ssl/ssl/server-crldir/a836cc2d.r0    |  18 +-
 .../ssl/ssl/server-multiple-alt-names.crt     |  36 +--
 src/test/ssl/ssl/server-no-names.crt          |  32 +--
 src/test/ssl/ssl/server-revoked.crt           |  33 +--
 src/test/ssl/ssl/server-single-alt-name.crt   |  34 +--
 src/test/ssl/ssl/server-ss.crt                |  19 --
 src/test/ssl/ssl/server-ss.key                |  27 --
 src/test/ssl/ssl/server.crl                   |  18 +-
 src/test/ssl/ssl/server_ca.crt                |  34 +--
 src/test/ssl/t/001_ssltests.pl                |   7 +-
 44 files changed, 668 insertions(+), 652 deletions(-)
 create mode 100644 src/test/ssl/client-revoked.config
 delete mode 100644 src/test/ssl/ssl/server-ss.crt
 delete mode 100644 src/test/ssl/ssl/server-ss.key

diff --git a/src/Makefile.global.in b/src/Makefile.global.in
index 8f05840821..0e4b331a80 100644
--- a/src/Makefile.global.in
+++ b/src/Makefile.global.in
@@ -32,8 +32,11 @@ all:
 # started to update the file.
 .DELETE_ON_ERROR:
 
-# Never delete any intermediate files automatically.
+# Never delete any intermediate files automatically unless the Makefile
+# explicitly asks for it.
+ifneq ($(clean_intermediates),yes)
 .SECONDARY:
+endif
 
 # PostgreSQL version number
 VERSION = @PACKAGE_VERSION@
diff --git a/src/test/ssl/Makefile b/src/test/ssl/Makefile
index a517756c94..6e67013f61 100644
--- a/src/test/ssl/Makefile
+++ b/src/test/ssl/Makefile
@@ -11,174 +11,213 @@
 
 subdir = src/test/ssl
 top_builddir = ../../..
+
+clean_intermediates := yes
 include $(top_builddir)/src/Makefile.global
 
 export with_ssl
 
-CERTIFICATES := server_ca server-cn-and-alt-names \
+#
+# To add a new server or client certificate, add a new <name>.config file in
+# this directory, then add <name> to either SERVERS or CLIENTS below. A
+# key/certificate pair will be generated for you, signed by the appropriate CA.
+#
+SERVERS := server-cn-and-alt-names \
 	server-cn-only server-single-alt-name server-multiple-alt-names \
-	server-no-names server-revoked server-ss \
-	client_ca client client-dn client-revoked \
-	root_ca
+	server-no-names server-revoked
+CLIENTS := client client-dn client-revoked
+
+#
+# To add a new non-standard key, add it to SPECIAL_KEYS and then add a recipe
+# for creating it to the "Special-case keys" section below.
+#
+SPECIAL_KEYS := ssl/server-password.key \
+	ssl/client-der.key ssl/client-encrypted-pem.key ssl/client-encrypted-der.key
 
-SSLFILES := $(CERTIFICATES:%=ssl/%.key) $(CERTIFICATES:%=ssl/%.crt) \
-	ssl/server-password.key \
-	ssl/client.crl ssl/server.crl ssl/root.crl \
+#
+# These files are just concatenations of other files. You can add new ones to
+# COMBINATIONS here, then declare the constituent files as dependencies in the
+# "Combined files" section below.
+#
+COMBINATIONS := \
 	ssl/both-cas-1.crt ssl/both-cas-2.crt \
 	ssl/root+server_ca.crt ssl/root+server.crl \
 	ssl/root+client_ca.crt ssl/root+client.crl \
-	ssl/client+client_ca.crt ssl/client-der.key \
-	ssl/client-encrypted-pem.key ssl/client-encrypted-der.key
+	ssl/client+client_ca.crt
 
+CERTIFICATES := root_ca server_ca client_ca $(SERVERS) $(CLIENTS)
+STANDARD_CERTS := $(CERTIFICATES:%=ssl/%.crt)
+STANDARD_KEYS := $(CERTIFICATES:%=ssl/%.key)
+CRLS := ssl/root.crl ssl/client.crl ssl/server.crl
+
+SSLFILES := $(STANDARD_CERTS) $(STANDARD_KEYS) $(SPECIAL_KEYS) $(COMBINATIONS) $(CRLS)
 SSLDIRS := ssl/client-crldir ssl/server-crldir \
 	ssl/root+client-crldir ssl/root+server-crldir
 
 # This target re-generates all the key and certificate files. Usually we just
 # use the ones that are committed to the tree without rebuilding them.
 #
-# This target will fail unless preceded by sslfiles-clean.
-#
+.PHONY: sslfiles
 sslfiles: $(SSLFILES) $(SSLDIRS)
 
-# OpenSSL requires a directory to put all generated certificates in. We don't
-# use this for anything, but we need a location.
-ssl/new_certs_dir:
-	mkdir ssl/new_certs_dir
+#
+# Special-case certificates
+#
 
-# Rule for creating private/public key pairs.
-ssl/%.key:
-	openssl genrsa -out $@ 2048
-	chmod 0600 $@
+# Root CA is self-signed.
+ssl/root_ca.crt: ssl/root_ca.key root_ca.config
+	openssl req -new -x509 -config root_ca.config -days 10000 -key $< -out $@
 
-# Root CA certificate
-ssl/root_ca.crt: ssl/root_ca.key cas.config
-	touch ssl/root_ca-certindex
-	openssl req -new -out ssl/root_ca.crt -x509 -config cas.config -config root_ca.config -key ssl/root_ca.key -days 10000 -extensions v3_ca
-	echo "01" > ssl/root_ca.srl
-
-# Client and server CAs
-ssl/%_ca.crt: ssl/%_ca.key %_ca.config ssl/root_ca.crt ssl/new_certs_dir
-	touch ssl/$*_ca-certindex
-	echo "unique_subject=no" > ssl/$*_ca-certindex.attr
-	openssl req -new -out ssl/temp_ca.crt -config cas.config -config $*_ca.config -key ssl/$*_ca.key
-# Sign the certificate with the root CA
-	openssl ca -name root_ca -batch -config cas.config -in ssl/temp_ca.crt -out ssl/temp_ca_signed.crt -extensions v3_ca
-	openssl x509 -in ssl/temp_ca_signed.crt -out ssl/$*_ca.crt # to keep just the PEM cert
-	rm ssl/temp_ca.crt ssl/temp_ca_signed.crt
-	echo "01" > ssl/$*_ca.srl
-
-# Server certificates, signed by server CA:
-ssl/server-%.crt: ssl/server-%.key ssl/server_ca.crt server-%.config
-	openssl req -new -key ssl/server-$*.key -out ssl/server-$*.csr -config server-$*.config
-	openssl ca -name server_ca -batch -config cas.config -in ssl/server-$*.csr -out ssl/temp.crt  -extensions v3_req -extfile server-$*.config
-	openssl x509 -in ssl/temp.crt -out ssl/server-$*.crt # to keep just the PEM cert
-	rm ssl/server-$*.csr
-
-# Self-signed version of server-cn-only.crt
-ssl/server-ss.crt: ssl/server-cn-only.key ssl/server-cn-only.crt server-cn-only.config
-	openssl req -new -key ssl/server-cn-only.key -out ssl/server-ss.csr -config server-cn-only.config
-	openssl x509 -req -days 10000 -in ssl/server-ss.csr -signkey ssl/server-cn-only.key -out ssl/server-ss.crt  -extensions v3_req -extfile server-cn-only.config
-	rm ssl/server-ss.csr
+#
+# Special-case keys
+#
+# All targets here are contained in $(SPECIAL_KEYS).
+#
 
 # Password-protected version of server-cn-only.key
 ssl/server-password.key: ssl/server-cn-only.key
 	openssl rsa -aes256 -in $< -out $@ -passout 'pass:secret1'
 
-# Client certificate, signed by the client CA:
-ssl/client.crt: ssl/client.key ssl/client_ca.crt
-	openssl req -new -key ssl/client.key -out ssl/client.csr -config client.config
-	openssl ca -name client_ca -batch -out ssl/temp.crt -config cas.config -infiles ssl/client.csr
-	openssl x509 -in ssl/temp.crt -out ssl/client.crt # to keep just the PEM cert
-	rm ssl/client.csr ssl/temp.crt
-
-# Client certificate with multi-part DN, signed by the client CA:
-ssl/client-dn.crt: ssl/client-dn.key ssl/client_ca.crt
-	openssl req -new -key ssl/client-dn.key -out ssl/client-dn.csr -config client-dn.config
-	openssl ca -name client_ca -batch -out ssl/temp.crt -config cas.config -infiles ssl/client-dn.csr
-	openssl x509 -in ssl/temp.crt -out ssl/client-dn.crt # to keep just the PEM cert
-	rm ssl/client-dn.csr ssl/temp.crt
-
-# Another client certificate, signed by the client CA. This one is revoked.
-ssl/client-revoked.crt: ssl/client-revoked.key ssl/client_ca.crt client.config
-	openssl req -new -key ssl/client-revoked.key -out ssl/client-revoked.csr -config client.config
-	openssl ca -name client_ca -batch -out ssl/temp.crt -config cas.config -infiles ssl/client-revoked.csr
-	openssl x509 -in ssl/temp.crt -out ssl/client-revoked.crt # to keep just the PEM cert
-	rm ssl/client-revoked.csr ssl/temp.crt
-
-# Convert the key to DER, to test our behaviour there too
+# DER-encoded version of client.key
 ssl/client-der.key: ssl/client.key
-	openssl rsa -in ssl/client.key -outform DER -out ssl/client-der.key
+	openssl rsa -in $< -outform DER -out $@
 
-# Convert the existing key to encrypted PEM (X.509 text) and DER (X.509 ASN.1) formats
+# Convert client.key to encrypted PEM (X.509 text) and DER (X.509 ASN.1) formats
 # to test libpq's support for the sslpassword= option.
-ssl/client-encrypted-pem.key: ssl/client.key
-	openssl rsa -in ssl/client.key -outform PEM -aes128 -passout 'pass:dUmmyP^#+' -out ssl/client-encrypted-pem.key
+ssl/client-encrypted-pem.key: outform := PEM
+ssl/client-encrypted-der.key: outform := DER
+ssl/client-encrypted-pem.key ssl/client-encrypted-der.key: ssl/client.key
+	openssl rsa -in $< -outform $(outform) -aes128 -passout 'pass:dUmmyP^#+' -out $@
 
-ssl/client-encrypted-der.key: ssl/client.key
-	openssl rsa -in ssl/client.key -outform DER -aes128 -passout 'pass:dUmmyP^#+' -out ssl/client-encrypted-der.key
+#
+# Combined files
+#
+# All targets in $(COMBINATIONS) share a single recipe; just declare the
+# necessary dependencies and they'll be smashed together.
+#
 
-# Root certificate files that contains both CA certificates, for testing
+# Root certificate file that contains both CA certificates, for testing
 # that multiple certificates can be used.
 ssl/both-cas-1.crt: ssl/root_ca.crt ssl/client_ca.crt ssl/server_ca.crt
-	cat $^ > $@
 
 # The same, but the certs are in different order
 ssl/both-cas-2.crt: ssl/root_ca.crt ssl/server_ca.crt ssl/client_ca.crt
-	cat $^ > $@
 
 # A root certificate file for the client, to validate server certs.
 ssl/root+server_ca.crt: ssl/root_ca.crt ssl/server_ca.crt
-	cat $^ > $@
 
 # and for the server, to validate client certs
 ssl/root+client_ca.crt: ssl/root_ca.crt ssl/client_ca.crt
-	cat $^ > $@
 
+# and for the client, to present to the server
 ssl/client+client_ca.crt: ssl/client.crt ssl/client_ca.crt
-	cat $^ > $@
-
-#### CRLs
-
-ssl/client.crl: ssl/client-revoked.crt
-	openssl ca -config cas.config -name client_ca -revoke ssl/client-revoked.crt
-	openssl ca -config cas.config -name client_ca -gencrl -out ssl/client.crl
-
-ssl/server.crl: ssl/server-revoked.crt
-	openssl ca -config cas.config -name server_ca -revoke ssl/server-revoked.crt
-	openssl ca -config cas.config -name server_ca -gencrl -out ssl/server.crl
-
-ssl/root.crl: ssl/root_ca.crt
-	openssl ca -config cas.config -name root_ca -gencrl -out ssl/root.crl
 
 # If a CRL is used, OpenSSL requires a CRL file for *all* the CAs in the
 # chain, even if some of them are empty.
 ssl/root+server.crl: ssl/root.crl ssl/server.crl
-	cat $^ > $@
 ssl/root+client.crl: ssl/root.crl ssl/client.crl
+
+$(COMBINATIONS):
 	cat $^ > $@
 
-ssl/root+server-crldir: ssl/server.crl ssl/root.crl
-	mkdir ssl/root+server-crldir
-	cp ssl/server.crl ssl/root+server-crldir/`openssl crl -hash -noout -in ssl/server.crl`.r0
-	cp ssl/root.crl ssl/root+server-crldir/`openssl crl -hash -noout -in ssl/root.crl`.r0
+#
+# Standard keys
+#
 
-ssl/root+client-crldir: ssl/client.crl ssl/root.crl
-	mkdir ssl/root+client-crldir
-	cp ssl/client.crl ssl/root+client-crldir/`openssl crl -hash -noout -in ssl/client.crl`.r0
-	cp ssl/root.crl ssl/root+client-crldir/`openssl crl -hash -noout -in ssl/root.crl`.r0
+$(STANDARD_KEYS):
+	openssl genrsa -out $@ 2048
+	chmod 0600 $@
 
-ssl/server-crldir: ssl/server.crl
-	mkdir ssl/server-crldir
-	cp ssl/server.crl ssl/server-crldir/`openssl crl -hash -noout -in ssl/server.crl`.r0
+#
+# Standard certificates
+#
+
+SERVER_CERTS := $(SERVERS:%=ssl/%.crt)
+CLIENT_CERTS := $(CLIENTS:%=ssl/%.crt)
+
+ssl/server_ca.crt ssl/client_ca.crt: ca := root_ca
+$(SERVER_CERTS): ca := server_ca
+$(CLIENT_CERTS): ca := client_ca
+
+ca_state_files = ssl/$(ca)-certindex ssl/$(ca)-certindex.attr ssl/$(ca).srl
+
+# This is the workhorse recipe. `openssl ca` can't be safely run from parallel
+# processes, so we must mark the entire Makefile .NOTPARALLEL. Enable
+# .SECONDEXPANSION so that the correct dependencies are determined by the value
+# of $(ca).
+.NOTPARALLEL:
+.SECONDEXPANSION: $(STANDARD_CERTS)
+ssl/%.crt: ssl/%.csr %.config ssl/$$(ca).crt | ssl/new_certs_dir $$(ca_state_files)
+	openssl ca -batch -config cas.config -name $(ca) -notext -in $< -out $@
+
+ssl/%.csr: ssl/%.key %.config
+	openssl req -new -key $< -out $@ -config $*.config
+
+#
+# CA State
+#
+# All of these are intended to be order-only dependencies; additionally, the
+# pattern recipes are intended to be intermediates, so do not name them
+# explicitly somewhere else in the Makefile. The goal is for Make to create the
+# state files once for each CA, allow them to accumulate whatever state is
+# needed, and then automatically remove them at the end of the run.
+#
+
+# OpenSSL requires a directory to put all generated certificates in. We don't
+# use this for anything, but we need a location.
+ssl/new_certs_dir:
+	mkdir $@
 
+ssl/%-certindex:
+	touch $@
+
+ssl/%-certindex.attr:
+	echo "unique_subject=no" > $@
+
+# The first serial number for each CA is based on the current timestamp, to
+# avoid collisions across Make runs.
+ssl/%.srl:
+	date +%Y%m%d%H%M%S00 > $@
+
+#
+# CRLs
+#
+
+ssl/root.crl: revoked :=
+ssl/root.crl: ca := root_ca
+
+ssl/client.crl: revoked := ssl/client-revoked.crt
+ssl/client.crl: ca := client_ca
+
+ssl/server.crl: revoked := ssl/server-revoked.crt
+ssl/server.crl: ca := server_ca
+
+.SECONDEXPANSION: $(CRLS)
+ssl/%.crl: ssl/$$(ca).crt $$(revoked) | $$(ca_state_files)
+	$(foreach cert,$(revoked),openssl ca -config cas.config -name $(ca) -revoke $(cert) &&) true
+	openssl ca -config cas.config -name $(ca) -gencrl -out $@
+
+#
+# CRL hash directories
+#
+
+ssl/root+server-crldir: ssl/server.crl ssl/root.crl
+ssl/root+client-crldir: ssl/client.crl ssl/root.crl
+ssl/server-crldir: ssl/server.crl
 ssl/client-crldir: ssl/client.crl
-	mkdir ssl/client-crldir
-	cp ssl/client.crl ssl/client-crldir/`openssl crl -hash -noout -in ssl/client.crl`.r0
+
+crlhashfile = $(shell openssl crl -hash -noout -in $(1)).r0
+
+ssl/%-crldir:
+	mkdir -p $@
+	rm -f $@/*.r0
+	$(foreach crl,$^,cp $(crl) $@/$(call crlhashfile,$(crl)) &&) true
+	touch $@
 
 .PHONY: sslfiles-clean
 sslfiles-clean:
-	rm -f $(SSLFILES) ssl/client_ca.srl ssl/server_ca.srl ssl/client_ca-certindex* ssl/server_ca-certindex* ssl/root_ca-certindex* ssl/root_ca.srl ssl/temp_ca.crt ssl/temp_ca_signed.crt
-	rm -rf $(SSLDIRS)
+	rm -f $(SSLFILES) ssl/*.old ssl/*.csr ssl/*.srl ssl/*-certindex*
+	rm -rf $(SSLDIRS) ssl/new_certs_dir
 
 clean distclean maintainer-clean:
 	rm -rf tmp_check
diff --git a/src/test/ssl/README b/src/test/ssl/README
index 84baa478ce..b9d96a637d 100644
--- a/src/test/ssl/README
+++ b/src/test/ssl/README
@@ -52,9 +52,6 @@ server-no-names
 	server certificates, with small variations in the hostnames present
         in the certificate. Signed by server_ca.
 
-server-ss
-	same as server-cn-only, but self-signed.
-
 server-password
 	same as server-cn-only, but password-protected.
 
diff --git a/src/test/ssl/cas.config b/src/test/ssl/cas.config
index 8c0ef6d82b..2c4851033a 100644
--- a/src/test/ssl/cas.config
+++ b/src/test/ssl/cas.config
@@ -1,12 +1,5 @@
 # This file contains the configuration for all the CAs.
 
-[ req ]
-prompt                 = no
-
-# Extensions for CA certs
-[ v3_ca ]
-basicConstraints = CA:true
-
 # Root CA, used to sign the certificates of the intermediary server and
 # client CAs.
 [ root_ca ]
@@ -21,6 +14,7 @@ private_key = ./ssl/root_ca.key
 new_certs_dir = ./ssl/new_certs_dir
 policy					= policy_match
 email_in_dn				= no
+copy_extensions			= copy
 
 # CA used to sign all the server certificates.
 [ server_ca ]
@@ -35,6 +29,7 @@ new_certs_dir = ./ssl/new_certs_dir
 serial = ./ssl/server_ca.srl
 policy					= policy_match
 email_in_dn				= no
+copy_extensions			= copy
 unique_subject = no
 crl = ./ssl/server.crl
 
@@ -51,6 +46,7 @@ new_certs_dir = ./ssl/new_certs_dir
 serial = ./ssl/client_ca.srl
 policy					= policy_match
 email_in_dn				= no
+copy_extensions			= copy
 unique_subject = no
 crl = ./ssl/client.crl
 
diff --git a/src/test/ssl/client-dn.config b/src/test/ssl/client-dn.config
index ee2df54bd6..0c71d83127 100644
--- a/src/test/ssl/client-dn.config
+++ b/src/test/ssl/client-dn.config
@@ -13,4 +13,3 @@ O 					   = PGDG
 CN                     = ssltestuser-dn
 
 # no extensions in client certs
-[ v3_req ]
diff --git a/src/test/ssl/client-revoked.config b/src/test/ssl/client-revoked.config
new file mode 100644
index 0000000000..3b82b57103
--- /dev/null
+++ b/src/test/ssl/client-revoked.config
@@ -0,0 +1,13 @@
+# An OpenSSL format CSR config file for creating a client certificate.
+#
+# This is identical to the client.config certificate, but this one is revoked
+# later.
+
+[ req ]
+distinguished_name     = req_distinguished_name
+prompt                 = no
+
+[ req_distinguished_name ]
+CN                     = ssltestuser
+
+# no extensions in client certs
diff --git a/src/test/ssl/client.config b/src/test/ssl/client.config
index 2e9d40d299..26fc2571f5 100644
--- a/src/test/ssl/client.config
+++ b/src/test/ssl/client.config
@@ -10,4 +10,3 @@ prompt                 = no
 CN                     = ssltestuser
 
 # no extensions in client certs
-[ v3_req ]
diff --git a/src/test/ssl/client_ca.config b/src/test/ssl/client_ca.config
index ef93d598c2..5990f06000 100644
--- a/src/test/ssl/client_ca.config
+++ b/src/test/ssl/client_ca.config
@@ -6,6 +6,11 @@
 [ req ]
 distinguished_name     = req_distinguished_name
 prompt                 = no
+req_extensions         = v3_ca
 
 [ req_distinguished_name ]
 CN                     = Test CA for PostgreSQL SSL regression test client certs
+
+# Extensions for CA certs
+[ v3_ca ]
+basicConstraints = CA:true
diff --git a/src/test/ssl/root_ca.config b/src/test/ssl/root_ca.config
index 187a9b8a46..e193186f8b 100644
--- a/src/test/ssl/root_ca.config
+++ b/src/test/ssl/root_ca.config
@@ -4,6 +4,7 @@
 [ req ]
 distinguished_name     = req_distinguished_name
 prompt                 = no
+x509_extensions        = v3_ca
 
 [ req_distinguished_name ]
 CN                     = Test root CA for PostgreSQL SSL regression test suite
diff --git a/src/test/ssl/server-cn-only.config b/src/test/ssl/server-cn-only.config
index 1e5d582213..9edb7b7aca 100644
--- a/src/test/ssl/server-cn-only.config
+++ b/src/test/ssl/server-cn-only.config
@@ -9,5 +9,4 @@ prompt                 = no
 CN = common-name.pg-ssltest.test
 OU = PostgreSQL test suite
 
-# For Subject Alternative Names
-[ v3_req ]
+# No Subject Alternative Names
diff --git a/src/test/ssl/server-no-names.config b/src/test/ssl/server-no-names.config
index 2a71125a42..89075dec83 100644
--- a/src/test/ssl/server-no-names.config
+++ b/src/test/ssl/server-no-names.config
@@ -10,7 +10,4 @@ prompt                 = no
 [ req_distinguished_name ]
 OU = PostgreSQL test suite
 
-# For Subject Alternative Names
-[ v3_req ]
-
-[ alt_names ]
+# No Subject Alternative Names
diff --git a/src/test/ssl/server-revoked.config b/src/test/ssl/server-revoked.config
index 47ef6462dc..c9e1f5d431 100644
--- a/src/test/ssl/server-revoked.config
+++ b/src/test/ssl/server-revoked.config
@@ -11,5 +11,4 @@ prompt                 = no
 CN = common-name.pg-ssltest.test
 OU = PostgreSQL test suite
 
-# For Subject Alternative Names
-[ v3_req ]
+# No Subject Alternative Names
diff --git a/src/test/ssl/server_ca.config b/src/test/ssl/server_ca.config
index d6126d5195..496aaba29f 100644
--- a/src/test/ssl/server_ca.config
+++ b/src/test/ssl/server_ca.config
@@ -6,6 +6,11 @@
 [ req ]
 distinguished_name     = req_distinguished_name
 prompt                 = no
+req_extensions         = v3_ca
 
 [ req_distinguished_name ]
 CN                     = Test CA for PostgreSQL SSL regression test server certs
+
+# Extensions for CA certs
+[ v3_ca ]
+basicConstraints = CA:true
diff --git a/src/test/ssl/ssl/both-cas-1.crt b/src/test/ssl/ssl/both-cas-1.crt
index 37ffa10174..4f4bc707d6 100644
--- a/src/test/ssl/ssl/both-cas-1.crt
+++ b/src/test/ssl/ssl/both-cas-1.crt
@@ -1,8 +1,8 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/both-cas-2.crt b/src/test/ssl/ssl/both-cas-2.crt
index 2f2723f2b1..01d0c4d6a4 100644
--- a/src/test/ssl/ssl/both-cas-2.crt
+++ b/src/test/ssl/ssl/both-cas-2.crt
@@ -1,8 +1,8 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
 -----BEGIN CERTIFICATE-----
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diff --git a/src/test/ssl/ssl/client+client_ca.crt b/src/test/ssl/ssl/client+client_ca.crt
index 2804527f3e..7fafa14de1 100644
--- a/src/test/ssl/ssl/client+client_ca.crt
+++ b/src/test/ssl/ssl/client+client_ca.crt
@@ -1,36 +1,37 @@
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diff --git a/src/test/ssl/ssl/client-crldir/9bb9e3c3.r0 b/src/test/ssl/ssl/client-crldir/9bb9e3c3.r0
index a667680e04..d93791b88a 100644
--- a/src/test/ssl/ssl/client-crldir/9bb9e3c3.r0
+++ b/src/test/ssl/ssl/client-crldir/9bb9e3c3.r0
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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 -----END X509 CRL-----
diff --git a/src/test/ssl/ssl/client-dn.crt b/src/test/ssl/ssl/client-dn.crt
index f2f6a62dad..0db14e5977 100644
--- a/src/test/ssl/ssl/client-dn.crt
+++ b/src/test/ssl/ssl/client-dn.crt
@@ -1,19 +1,19 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/client-revoked.crt b/src/test/ssl/ssl/client-revoked.crt
index 14857a33a2..51ebe924a6 100644
--- a/src/test/ssl/ssl/client-revoked.crt
+++ b/src/test/ssl/ssl/client-revoked.crt
@@ -1,17 +1,18 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/client.crl b/src/test/ssl/ssl/client.crl
index a667680e04..d93791b88a 100644
--- a/src/test/ssl/ssl/client.crl
+++ b/src/test/ssl/ssl/client.crl
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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 -----END X509 CRL-----
diff --git a/src/test/ssl/ssl/client.crt b/src/test/ssl/ssl/client.crt
index 4d0a6ef419..1f6ae05fe4 100644
--- a/src/test/ssl/ssl/client.crt
+++ b/src/test/ssl/ssl/client.crt
@@ -1,17 +1,18 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/client_ca.crt b/src/test/ssl/ssl/client_ca.crt
index 1ef3771261..ef48749f76 100644
--- a/src/test/ssl/ssl/client_ca.crt
+++ b/src/test/ssl/ssl/client_ca.crt
@@ -1,19 +1,19 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/root+client-crldir/9bb9e3c3.r0 b/src/test/ssl/ssl/root+client-crldir/9bb9e3c3.r0
index a667680e04..d93791b88a 100644
--- a/src/test/ssl/ssl/root+client-crldir/9bb9e3c3.r0
+++ b/src/test/ssl/ssl/root+client-crldir/9bb9e3c3.r0
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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 -----END X509 CRL-----
diff --git a/src/test/ssl/ssl/root+client-crldir/a3d11bff.r0 b/src/test/ssl/ssl/root+client-crldir/a3d11bff.r0
index e879cf25a7..5b42d3803f 100644
--- a/src/test/ssl/ssl/root+client-crldir/a3d11bff.r0
+++ b/src/test/ssl/ssl/root+client-crldir/a3d11bff.r0
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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index 854d77b71e..02eff4d326 100644
--- a/src/test/ssl/ssl/root+client.crl
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diff --git a/src/test/ssl/ssl/root+client_ca.crt b/src/test/ssl/ssl/root+client_ca.crt
index 1867cd9c31..7819c54828 100644
--- a/src/test/ssl/ssl/root+client_ca.crt
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diff --git a/src/test/ssl/ssl/root+server-crldir/a3d11bff.r0 b/src/test/ssl/ssl/root+server-crldir/a3d11bff.r0
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--- a/src/test/ssl/ssl/root+server-crldir/a3d11bff.r0
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diff --git a/src/test/ssl/ssl/root+server-crldir/a836cc2d.r0 b/src/test/ssl/ssl/root+server-crldir/a836cc2d.r0
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diff --git a/src/test/ssl/ssl/root+server_ca.crt b/src/test/ssl/ssl/root+server_ca.crt
index 861eba80d0..5074f4fa9b 100644
--- a/src/test/ssl/ssl/root+server_ca.crt
+++ b/src/test/ssl/ssl/root+server_ca.crt
@@ -1,8 +1,8 @@
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diff --git a/src/test/ssl/ssl/root.crl b/src/test/ssl/ssl/root.crl
index e879cf25a7..5b42d3803f 100644
--- a/src/test/ssl/ssl/root.crl
+++ b/src/test/ssl/ssl/root.crl
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diff --git a/src/test/ssl/ssl/root_ca.crt b/src/test/ssl/ssl/root_ca.crt
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--- a/src/test/ssl/ssl/root_ca.crt
+++ b/src/test/ssl/ssl/root_ca.crt
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diff --git a/src/test/ssl/ssl/server-cn-and-alt-names.crt b/src/test/ssl/ssl/server-cn-and-alt-names.crt
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--- a/src/test/ssl/ssl/server-cn-and-alt-names.crt
+++ b/src/test/ssl/ssl/server-cn-and-alt-names.crt
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-cn-only.crt b/src/test/ssl/ssl/server-cn-only.crt
index 67bf0b1645..acdf6f1a75 100644
--- a/src/test/ssl/ssl/server-cn-only.crt
+++ b/src/test/ssl/ssl/server-cn-only.crt
@@ -1,18 +1,19 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-crldir/a836cc2d.r0 b/src/test/ssl/ssl/server-crldir/a836cc2d.r0
index 717951c26a..331a83cb62 100644
--- a/src/test/ssl/ssl/server-crldir/a836cc2d.r0
+++ b/src/test/ssl/ssl/server-crldir/a836cc2d.r0
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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 -----END X509 CRL-----
diff --git a/src/test/ssl/ssl/server-multiple-alt-names.crt b/src/test/ssl/ssl/server-multiple-alt-names.crt
index 158153d10c..58799e49f8 100644
--- a/src/test/ssl/ssl/server-multiple-alt-names.crt
+++ b/src/test/ssl/ssl/server-multiple-alt-names.crt
@@ -1,20 +1,20 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-no-names.crt b/src/test/ssl/ssl/server-no-names.crt
index 97e11176f6..b5d0589090 100644
--- a/src/test/ssl/ssl/server-no-names.crt
+++ b/src/test/ssl/ssl/server-no-names.crt
@@ -1,18 +1,18 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-revoked.crt b/src/test/ssl/ssl/server-revoked.crt
index 1ca5e6d3ef..3bb0f164a6 100644
--- a/src/test/ssl/ssl/server-revoked.crt
+++ b/src/test/ssl/ssl/server-revoked.crt
@@ -1,18 +1,19 @@
 -----BEGIN CERTIFICATE-----
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+XRwVulaWJQ==
 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-single-alt-name.crt b/src/test/ssl/ssl/server-single-alt-name.crt
index e7403f3a6b..7affdd68e7 100644
--- a/src/test/ssl/ssl/server-single-alt-name.crt
+++ b/src/test/ssl/ssl/server-single-alt-name.crt
@@ -1,19 +1,19 @@
 -----BEGIN CERTIFICATE-----
-MIIDCzCCAfOgAwIBAgIBAzANBgkqhkiG9w0BAQsFADBCMUAwPgYDVQQDDDdUZXN0
-IENBIGZvciBQb3N0Z3JlU1FMIFNTTCByZWdyZXNzaW9uIHRlc3Qgc2VydmVyIGNl
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-v/Co7oiMyTrCqyCsWOBu
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+kYtgAdzftiCSrbDjl1pzPSM6RC/E/A==
 -----END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-ss.crt b/src/test/ssl/ssl/server-ss.crt
deleted file mode 100644
index d775e6029a..0000000000
--- a/src/test/ssl/ssl/server-ss.crt
+++ /dev/null
@@ -1,19 +0,0 @@
------BEGIN CERTIFICATE-----
-MIIDGDCCAgCgAwIBAgIUVR71MjsbvBO6T1gJQaL/6hMwhqQwDQYJKoZIhvcNAQEL
-BQAwRjEkMCIGA1UEAwwbY29tbW9uLW5hbWUucGctc3NsdGVzdC50ZXN0MR4wHAYD
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-Lm8ez0WBPebV69sim431iJcVcxxBbFd4qUJ9cHIc7VO2mSaazsIOzbd400POF/vk
-gfpDs48GfnZ+X3hgoQA4u7eudLqttI+j1xV+IHlCtaa1nDHymUrN/FhI1x+6c1SU
-V12eHqVatPMe0d+OCJPqIL9lbe+sGXlxDkMqAQ==
------END CERTIFICATE-----
diff --git a/src/test/ssl/ssl/server-ss.key b/src/test/ssl/ssl/server-ss.key
deleted file mode 100644
index a5e7f4bbfa..0000000000
--- a/src/test/ssl/ssl/server-ss.key
+++ /dev/null
@@ -1,27 +0,0 @@
------BEGIN RSA PRIVATE KEY-----
-MIIEpQIBAAKCAQEAttI8Qu3wJgwp9RqLEqgO5GlYdA4bG+OyB4y+Bx4DQ7fhaJvJ
-vwBfY8ig+nPZU5WJNDyoaPtDg2uQwWbUq9WXkdktAxelrisQ/oJiCscPARlAIM6U
-XPOXai10XQ6QsMaaa6cXIGkMZVfhYEbuN0Q8TJSC1MbSQ/TtCnWxMRmktRv5xx8y
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-E8fK2ttvxAqDf8s3MChnXbMN6QrzaGSS44oZKwIDAQABAoIBAQCsMhjQcYxgSdS7
-J+UWDXT5bsABj8e43R4yPj4+NeadQfTtss6zOIagVbhKLhPkxlQU/40gVIminw4Z
-G+H0d5nrpcLfxsYm5il7jxMJU7SuNDpSrEDRzB4xw952R+HAn0+TVi5SOJ+UVNHS
-/Pwi0gJ5nugbwakKmQcrcu8ScDTS34yFScMIRUYiKQ44TDiDtwyL07sc4ob1X/uY
-na1GnyOBjYEg+9nRwmV+QZwPjyP3Qe81rvH7saV2R2oc4uFU151KtoIT96V4FnpD
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-bc8VxL7MHWHQSMVKAL3jYTBcEXDBdUnqODY5D1xGoeh8uamtrtkpF860GNss2Its
-MMjkbjNFF7ggG5sCtcGceu7bguqf70sAf/TQlJyD2fLeuuLXuD45c0QJVcsRToPu
-dVXoLkkCgYEA5JkhCPE9a2ssrqi1ZFt3FAayulycM+r+wJY7zNIwv/ydzbE5D4Ar
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-Nc/5RLjEeophXb4f3WPjMBliYGX0tOPhT+buHep+f0enxgO8Z2a4Omg=
------END RSA PRIVATE KEY-----
diff --git a/src/test/ssl/ssl/server.crl b/src/test/ssl/ssl/server.crl
index 717951c26a..331a83cb62 100644
--- a/src/test/ssl/ssl/server.crl
+++ b/src/test/ssl/ssl/server.crl
@@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
-MIIBnjCBhzANBgkqhkiG9w0BAQsFADBCMUAwPgYDVQQDDDdUZXN0IENBIGZvciBQ
-b3N0Z3JlU1FMIFNTTCByZWdyZXNzaW9uIHRlc3Qgc2VydmVyIGNlcnRzFw0xODEx
-MjcxMzQwNTVaFw00NjA0MTQxMzQwNTVaMBQwEgIBBhcNMTgxMTI3MTM0MDU1WjAN
-BgkqhkiG9w0BAQsFAAOCAQEAbVuJXemxM6HLlIHGWlQvVmsmG4ZTQWiDnZjfmrND
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-nmObJtVdIu3bVlWIlDXaP5Emk3d7ouCj5f8Kyeb8gm4pL3N6e0eI63hCaS39hhE6
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-SEXWtgjMRXiIHbtU0va3LhSH5OSW0mh+L9oGUQDYnyuudnWGpulhqIp4qVkJRDDu
-41HpD83dV2uRtBLvc25AFHj7kXBflbO3gvGZVPYf1zVghQ==
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+B18ch9rbBltz+Y4R63rCN9MdsnGXf6PQ6a6doZhSI1pnDrui12MOQrU=
 -----END X509 CRL-----
diff --git a/src/test/ssl/ssl/server_ca.crt b/src/test/ssl/ssl/server_ca.crt
index 9f727bf9e9..0d6d7a6f82 100644
--- a/src/test/ssl/ssl/server_ca.crt
+++ b/src/test/ssl/ssl/server_ca.crt
@@ -1,19 +1,19 @@
 -----BEGIN CERTIFICATE-----
-MIIDDTCCAfWgAwIBAgIBATANBgkqhkiG9w0BAQsFADBAMT4wPAYDVQQDDDVUZXN0
-IHJvb3QgQ0EgZm9yIFBvc3RncmVTUUwgU1NMIHJlZ3Jlc3Npb24gdGVzdCBzdWl0
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-JZ3CEMu8/WA5uQBXdQUozlE=
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+/50ELwT++0n0KWVXNHrDNfI5Gaa+SxClAsPsei2jLKpgR6QFC3wn38Z9q9LjAVuC
++FWhoN1uhYeoricEXwIDAQABoxAwDjAMBgNVHRMEBTADAQH/MA0GCSqGSIb3DQEB
+CwUAA4IBAQCdCA/EoXrustoV4jJGbkdXDuOUkBurwggSNBAqUBSDvCohRoD77Ecb
+QVuzPNxWKG+E4PwfUq2ha+2yPONEJ28ZgsbHq5qlJDMJ43wlcjn6wmmAJNeSpO8F
+0V9d2X/4wNZty9/zbwTnw26KChgDHumQ0WIbCoBtdqy8KDswYOvpgws6dqc021I7
+UrFo6vZek7VoApbJgkDL6qYADa6ApfW43ThH4sViFITeYt/kSHgmy2Udhs34jMM8
+xsFP/uYpRi1b1glenwSIKiHjD4/C9vnWQt5K3gRBvYukEj2Bw9VkNRpBVCi0cOoA
+OuwX3bwzNYNbZQv4K66oRpvuoEjCNeHg
 -----END CERTIFICATE-----
diff --git a/src/test/ssl/t/001_ssltests.pl b/src/test/ssl/t/001_ssltests.pl
index 44daefb002..0ff3564742 100644
--- a/src/test/ssl/t/001_ssltests.pl
+++ b/src/test/ssl/t/001_ssltests.pl
@@ -485,6 +485,11 @@ TODO:
 }
 
 # pg_stat_ssl
+
+my $serialno = `openssl x509 -serial -noout -in ssl/client.crt`;
+$serialno =~ s/^serial=//;
+$serialno = hex($serialno); # OpenSSL prints serial numbers in hexadecimal
+
 command_like(
 	[
 		'psql',
@@ -500,7 +505,7 @@ command_like(
 		"SELECT * FROM pg_stat_ssl WHERE pid = pg_backend_pid()"
 	],
 	qr{^pid,ssl,version,cipher,bits,client_dn,client_serial,issuer_dn\r?\n
-				^\d+,t,TLSv[\d.]+,[\w-]+,\d+,/CN=ssltestuser,1,\Q/CN=Test CA for PostgreSQL SSL regression test client certs\E\r?$}mx,
+				^\d+,t,TLSv[\d.]+,[\w-]+,\d+,/CN=ssltestuser,$serialno,\Q/CN=Test CA for PostgreSQL SSL regression test client certs\E\r?$}mx,
 	'pg_stat_ssl with client certificate');
 
 # client key with wrong permissions
-- 
2.25.1

Re: [PATCH] test/ssl: rework the sslfiles Makefile target

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