Refactor the sslfiles Makefile target for ease of use

The Makefile handling of certificate and keypairs used for TLS testing had become quite difficult to work with. Adding a new cert without the need to regenerate everything was too complicated. This patch refactors the sslfiles make target such that adding a new certificate requires only adding a .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). - all configuration files underneath the conf/ directory. The target is moved to its own makefile in order to avoid colliding with global make settings. Author: Jacob Champion <pchampion@vmware.com> Reviewed-by: Michael Paquier <michael@paquier.xyz> Discussion: https://postgr.es/m/d15a9838344ba090e09fd866abf913584ea19fb7.camel@vmware.com
4 years ago · b4c4a00ead
parent 3e310d837a
commit b4c4a00ead
45 changed files with 778 additions and 652 deletions
--- a/src/test/ssl/Makefile
+++ b/src/test/ssl/Makefile
@ -15,170 +15,17 @@ include $(top_builddir)/src/Makefile.global

 export with_ssl

-CERTIFICATES := server_ca server-cn-and-alt-names \
-	server-cn-only server-single-alt-name server-multiple-alt-names \
-	server-no-names server-revoked \
-	client_ca client client-dn client-revoked \
-	root_ca
-
-SSLFILES := $(CERTIFICATES:%=ssl/%.key) $(CERTIFICATES:%=ssl/%.crt) \
-	ssl/server-password.key \
-	ssl/client.crl ssl/server.crl ssl/root.crl \
-	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
-
-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.
-#
-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
-
-# Rule for creating private/public key pairs.
-ssl/%.key:
-	openssl genrsa -out $@ 2048
-	chmod 0600 $@
-
-# Root CA certificate
-ssl/root_ca.crt: ssl/root_ca.key cas.config
-	touch ssl/root_ca-certindex
-	openssl req -new -out ssl/root_ca.crt -x509 -config cas.config -config root_ca.config -key ssl/root_ca.key -days 10000 -extensions v3_ca
-	echo "01" > ssl/root_ca.srl
-
-# Client and server CAs
-ssl/%_ca.crt: ssl/%_ca.key %_ca.config ssl/root_ca.crt ssl/new_certs_dir
-	touch ssl/$*_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
-
-# 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
-ssl/client-der.key: ssl/client.key
-	openssl rsa -in ssl/client.key -outform DER -out ssl/client-der.key
-
-# Convert the existing 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-der.key: ssl/client.key
-	openssl rsa -in ssl/client.key -outform DER -aes128 -passout 'pass:dUmmyP^#+' -out ssl/client-encrypted-der.key
-
-# Root certificate files 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 $^ > $@
-
-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
-	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
-
-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
-
-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
-
-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
-
-.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)
+# The sslfiles targets are separated into their own file due to interactions
+# with settings in Makefile.global.
+.PHONY: sslfiles sslfiles-clean
+sslfiles sslfiles-clean:
+	$(MAKE) -f sslfiles.mk $@

 clean distclean maintainer-clean:
 	rm -rf tmp_check
-	rm -rf ssl/*.old ssl/new_certs_dir ssl/client*_tmp.key
+	$(MAKE) -f sslfiles.mk $@

-# Doesn't depend on $(SSLFILES) because we don't rebuild them by default
+# Doesn't depend on sslfiles because we don't rebuild them by default
 check:
 	$(prove_check)

--- a/src/test/ssl/README
+++ b/src/test/ssl/README
@ -85,7 +85,9 @@ There are also CRLs for each of the CAs: root.crl, server.crl and client.crl.

 For convenience, all of these keypairs and certificates are included in the
 ssl/ subdirectory. The Makefile also contains a rule, "make sslfiles", to
-recreate them if you need to make changes.
+recreate them if you need to make changes. "make sslfiles-clean" is required
+in order to recreate the full set of keypairs and certificates. To rebuild
+separate files, touch (or remove) the files in question and run "make sslfiles".

 TODO
 ====
--- a/src/test/ssl/conf/cas.config
+++ b/src/test/ssl/conf/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

--- a/src/test/ssl/conf/client-dn.config
+++ b/src/test/ssl/conf/client-dn.config
@ -13,4 +13,3 @@ O 					   = PGDG
 CN                     = ssltestuser-dn

 # no extensions in client certs
-[ v3_req ]
--- a/src/test/ssl/conf/client-revoked.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/client.config
+++ b/src/test/ssl/conf/client.config
@ -10,4 +10,3 @@ prompt                 = no
 CN                     = ssltestuser

 # no extensions in client certs
-[ v3_req ]
--- a/src/test/ssl/conf/client_ca.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/root_ca.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/server-cn-and-alt-names.config
+++ b/src/test/ssl/conf/server-cn-and-alt-names.config
--- a/src/test/ssl/conf/server-cn-only.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/server-multiple-alt-names.config
+++ b/src/test/ssl/conf/server-multiple-alt-names.config
--- a/src/test/ssl/conf/server-no-names.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/server-revoked.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/conf/server-single-alt-name.config
+++ b/src/test/ssl/conf/server-single-alt-name.config
--- a/src/test/ssl/conf/server_ca.config
+++ b/src/test/ssl/conf/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
--- a/src/test/ssl/ssl/both-cas-1.crt
+++ b/src/test/ssl/ssl/both-cas-1.crt
@ -1,8 +1,8 @@
 -----BEGIN CERTIFICATE-----
-MIIDHjCCAgagAwIBAgIUEAgXJ/ibw6TVTUoomlBsPMfVTlMwDQYJKoZIhvcNAQEL
+MIIDHjCCAgagAwIBAgIUF+e8lCA0vD0zKtxIDVPdDY/IkgUwDQYJKoZIhvcNAQEL
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 -----END CERTIFICATE-----
 -----BEGIN CERTIFICATE-----
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@ -1,8 +1,8 @@
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 -----END CERTIFICATE-----
--- 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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+++ b/src/test/ssl/ssl/client-crldir/9bb9e3c3.r0
@ -1,11 +1,11 @@
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@ -1,19 +1,19 @@
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 -----END CERTIFICATE-----
--- a/src/test/ssl/ssl/client-revoked.crt
+++ b/src/test/ssl/ssl/client-revoked.crt
@ -1,17 +1,18 @@
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 -----END CERTIFICATE-----
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--- a/src/test/ssl/ssl/client.crt
+++ b/src/test/ssl/ssl/client.crt
@ -1,17 +1,18 @@
 -----BEGIN CERTIFICATE-----
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--- a/src/test/ssl/ssl/client_ca.crt
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@ -1,19 +1,19 @@
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+++ b/src/test/ssl/ssl/root+client-crldir/9bb9e3c3.r0
@ -1,11 +1,11 @@
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--- a/src/test/ssl/ssl/root+client_ca.crt
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@ -1,8 +1,8 @@
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 -----END X509 CRL-----
--- a/src/test/ssl/ssl/root_ca.crt
+++ b/src/test/ssl/ssl/root_ca.crt
@ -1,8 +1,8 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
--- a/src/test/ssl/ssl/server-cn-and-alt-names.crt
+++ b/src/test/ssl/ssl/server-cn-and-alt-names.crt
@ -1,20 +1,20 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
--- 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-----
--- 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-----
--- 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-----
--- 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-----
--- 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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 -----END CERTIFICATE-----
--- 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-----
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 -----END CERTIFICATE-----
--- a/src/test/ssl/ssl/server.crl
+++ b/src/test/ssl/ssl/server.crl
@ -1,11 +1,11 @@
 -----BEGIN X509 CRL-----
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 -----END X509 CRL-----
--- a/src/test/ssl/ssl/server_ca.crt
+++ b/src/test/ssl/ssl/server_ca.crt
@ -1,19 +1,19 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
--- a/src/test/ssl/sslfiles.mk
+++ b/src/test/ssl/sslfiles.mk
@ -0,0 +1,244 @@
+#-------------------------------------------------------------------------
+#
+# Makefile for sslfiles
+#
+#   The SSL test files are completely disjoint from the rest of the build; they
+#   don't rely on other targets or on Makefile.global. Since these recipes rely
+#   on some default Make behavior that's disabled in the main build tree, such
+#   as intermediate cleanup, they've been moved into their own separate file.
+#   The main Makefile in this directory defers to this helper file when
+#   building the sslfiles-related targets.
+#
+# Portions Copyright (c) 1996-2021, PostgreSQL Global Development Group
+# Portions Copyright (c) 1994, Regents of the University of California
+#
+# src/test/ssl/sslfiles.mk
+#
+#-------------------------------------------------------------------------
+
+#
+# To add a new server or client certificate, add a new <name>.config file in
+# the conf/ 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
+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
+
+#
+# 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
+
+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.
+#
+.PHONY: sslfiles
+sslfiles: $(SSLFILES) $(SSLDIRS)
+
+#
+# Special-case certificates
+#
+
+# Root CA is self-signed.
+ssl/root_ca.crt: ssl/root_ca.key conf/root_ca.config
+	openssl req -new -x509 -config conf/root_ca.config -days 10000 -key $< -out $@
+
+#
+# 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'
+
+# DER-encoded version of client.key
+ssl/client-der.key: ssl/client.key
+	openssl rsa -in $< -outform DER -out $@
+
+# 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 $< -outform PEM -aes128 -passout 'pass:dUmmyP^#+' -out $@
+# TODO Explicitly choosing -aes128 generates a key unusable to PostgreSQL with
+# OpenSSL 3.0.0, so fall back on the default for now.
+ssl/client-encrypted-der.key: ssl/client.key
+	openssl rsa -in $< -outform DER -passout 'pass:dUmmyP^#+' -out $@
+
+#
+# Combined files
+#
+# All targets in $(COMBINATIONS) share a single recipe; just declare the
+# necessary dependencies and they'll be smashed together.
+#
+
+# Root certificate file that contains both CA certificates, for testing
+# that multiple certificates can be used.
+ssl/both-cas-1.crt: ssl/root_ca.crt ssl/client_ca.crt ssl/server_ca.crt
+
+# The same, but the certs are in different order
+ssl/both-cas-2.crt: ssl/root_ca.crt ssl/server_ca.crt ssl/client_ca.crt
+
+# A root certificate file for the client, to validate server certs.
+ssl/root+server_ca.crt: ssl/root_ca.crt ssl/server_ca.crt
+
+# and for the server, to validate client certs
+ssl/root+client_ca.crt: ssl/root_ca.crt ssl/client_ca.crt
+
+# and for the client, to present to the server
+ssl/client+client_ca.crt: ssl/client.crt ssl/client_ca.crt
+
+# If a CRL is used, OpenSSL requires a CRL file for *all* the CAs in the
+# chain, even if some of them are empty.
+ssl/root+server.crl: ssl/root.crl ssl/server.crl
+ssl/root+client.crl: ssl/root.crl ssl/client.crl
+
+$(COMBINATIONS):
+	cat $^ > $@
+
+#
+# Standard keys
+#
+
+$(STANDARD_KEYS):
+	openssl genrsa -out $@ 2048
+	chmod 0600 $@
+
+#
+# Standard certificates
+#
+
+CA_CERTS     := ssl/server_ca.crt ssl/client_ca.crt
+SERVER_CERTS := $(SERVERS:%=ssl/%.crt)
+CLIENT_CERTS := $(CLIENTS:%=ssl/%.crt)
+
+# See the "CA State" section below.
+root_ca_state_files := ssl/root_ca-certindex ssl/root_ca-certindex.attr ssl/root_ca.srl
+server_ca_state_files := ssl/server_ca-certindex ssl/server_ca-certindex.attr ssl/server_ca.srl
+client_ca_state_files := ssl/client_ca-certindex ssl/client_ca-certindex.attr ssl/client_ca.srl
+
+# These are the workhorse recipes. `openssl ca` can't be safely run from
+# parallel processes, so we must mark the entire Makefile .NOTPARALLEL.
+.NOTPARALLEL:
+$(CA_CERTS): ssl/%.crt: ssl/%.csr conf/%.config conf/cas.config ssl/root_ca.crt | ssl/new_certs_dir $(root_ca_state_files)
+	openssl ca -batch -config conf/cas.config -name root_ca   -notext -in $< -out $@
+
+$(SERVER_CERTS): ssl/%.crt: ssl/%.csr conf/%.config conf/cas.config ssl/server_ca.crt | ssl/new_certs_dir $(server_ca_state_files)
+	openssl ca -batch -config conf/cas.config -name server_ca -notext -in $< -out $@
+
+$(CLIENT_CERTS): ssl/%.crt: ssl/%.csr conf/%.config conf/cas.config ssl/client_ca.crt | ssl/new_certs_dir $(client_ca_state_files)
+	openssl ca -batch -config conf/cas.config -name client_ca -notext -in $< -out $@
+
+# The CSRs don't need to persist after a build.
+.INTERMEDIATE: $(CERTIFICATES:%=ssl/%.csr)
+ssl/%.csr: ssl/%.key conf/%.config
+	openssl req -new -key $< -out $@ -config conf/$*.config
+
+#
+# CA State
+#
+# All of these are intended to be order-only dependencies; additionally, the
+# pattern recipes are marked as explicit intermediates. 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.
+#
+
+.INTERMEDIATE: $(root_ca_state_files) $(server_ca_state_files) $(client_ca_state_files)
+
+# 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: ssl/root_ca.crt | $(root_ca_state_files)
+	openssl ca -config conf/cas.config -name root_ca   -gencrl -out $@
+
+ssl/server.crl: ssl/server-revoked.crt ssl/server_ca.crt | $(server_ca_state_files)
+	openssl ca -config conf/cas.config -name server_ca -revoke $<
+	openssl ca -config conf/cas.config -name server_ca -gencrl -out $@
+
+ssl/client.crl: ssl/client-revoked.crt ssl/client_ca.crt | $(client_ca_state_files)
+	openssl ca -config conf/cas.config -name client_ca -revoke $<
+	openssl ca -config conf/cas.config -name client_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
+
+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/*.old ssl/*.csr ssl/*.srl ssl/*-certindex*
+	rm -rf $(SSLDIRS) ssl/new_certs_dir
+
+# The difference between the below clean targets and sslfiles-clean is that the
+# clean targets will be run during a "standard" recursive clean run from the
+# main build tree. The sslfiles-clean target must be run explicitly from this
+# directory.
+.PHONY: clean distclean maintainer-clean
+clean distclean maintainer-clean:
+	rm -rf ssl/*.old ssl/new_certs_dir ssl/client*_tmp.key
--- a/src/test/ssl/t/001_ssltests.pl
+++ b/src/test/ssl/t/001_ssltests.pl
@ -485,6 +485,21 @@ TODO:
 }

 # pg_stat_ssl
+
+my $serialno = `openssl x509 -serial -noout -in ssl/client.crt`;
+if ($? == 0)
+{
+	$serialno =~ s/^serial=//;
+	$serialno = hex($serialno); # OpenSSL prints serial numbers in hexadecimal
+}
+else
+{
+	# OpenSSL isn't functioning on the user's PATH. This probably isn't worth
+	# skipping the test over, so just fall back to a generic integer match.
+	warn 'couldn\'t run `openssl x509` to get client cert serialno';
+	$serialno = '\d+';
+}
+
 command_like(
 	[
 		'psql',
@ -500,7 +515,7 @@ command_like(
 		"SELECT * FROM pg_stat_ssl WHERE pid = pg_backend_pid()"
 	],
 	qr{^pid,ssl,version,cipher,bits,client_dn,client_serial,issuer_dn\r?\n
-				^\d+,t,TLSv[\d.]+,[\w-]+,\d+,/CN=ssltestuser,1,\Q/CN=Test CA for PostgreSQL SSL regression test client certs\E\r?$}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