diff --git a/contrib/pgcrypto/Makefile b/contrib/pgcrypto/Makefile
index 7fb59f51b7..5efa10c334 100644
--- a/contrib/pgcrypto/Makefile
+++ b/contrib/pgcrypto/Makefile
@@ -42,7 +42,7 @@ PGFILEDESC = "pgcrypto - cryptographic functions"
 REGRESS = init md5 sha1 hmac-md5 hmac-sha1 blowfish rijndael \
 	sha2 des 3des cast5 \
 	crypt-des crypt-md5 crypt-blowfish crypt-xdes \
-	pgp-armor pgp-decrypt pgp-encrypt $(CF_PGP_TESTS) \
+	pgp-armor pgp-decrypt pgp-encrypt pgp-encrypt-md5 $(CF_PGP_TESTS) \
 	pgp-pubkey-decrypt pgp-pubkey-encrypt pgp-info
 
 EXTRA_CLEAN = gen-rtab
diff --git a/contrib/pgcrypto/expected/crypt-md5_1.out b/contrib/pgcrypto/expected/crypt-md5_1.out
new file mode 100644
index 0000000000..0ffda34ab4
--- /dev/null
+++ b/contrib/pgcrypto/expected/crypt-md5_1.out
@@ -0,0 +1,16 @@
+--
+-- crypt() and gen_salt(): md5
+--
+SELECT crypt('', '$1$Szzz0yzz');
+ERROR:  crypt(3) returned NULL
+SELECT crypt('foox', '$1$Szzz0yzz');
+ERROR:  crypt(3) returned NULL
+CREATE TABLE ctest (data text, res text, salt text);
+INSERT INTO ctest VALUES ('password', '', '');
+UPDATE ctest SET salt = gen_salt('md5');
+UPDATE ctest SET res = crypt(data, salt);
+ERROR:  crypt(3) returned NULL
+SELECT res = crypt(data, res) AS "worked"
+FROM ctest;
+ERROR:  invalid salt
+DROP TABLE ctest;
diff --git a/contrib/pgcrypto/expected/hmac-md5_1.out b/contrib/pgcrypto/expected/hmac-md5_1.out
new file mode 100644
index 0000000000..56875b0f63
--- /dev/null
+++ b/contrib/pgcrypto/expected/hmac-md5_1.out
@@ -0,0 +1,44 @@
+--
+-- HMAC-MD5
+--
+SELECT hmac(
+'Hi There',
+'\x0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 2
+SELECT hmac(
+'Jefe',
+'what do ya want for nothing?',
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 3
+SELECT hmac(
+'\xdddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddd'::bytea,
+'\xaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 4
+SELECT hmac(
+'\xcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcdcd'::bytea,
+'\x0102030405060708090a0b0c0d0e0f10111213141516171819'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 5
+SELECT hmac(
+'Test With Truncation',
+'\x0c0c0c0c0c0c0c0c0c0c0c0c0c0c0c0c'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 6
+SELECT hmac(
+'Test Using Larger Than Block-Size Key - Hash Key First',
+'\xaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+-- 7
+SELECT hmac(
+'Test Using Larger Than Block-Size Key and Larger Than One Block-Size Data',
+'\xaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa'::bytea,
+'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
diff --git a/contrib/pgcrypto/expected/md5_1.out b/contrib/pgcrypto/expected/md5_1.out
new file mode 100644
index 0000000000..decb215c48
--- /dev/null
+++ b/contrib/pgcrypto/expected/md5_1.out
@@ -0,0 +1,17 @@
+--
+-- MD5 message digest
+--
+SELECT digest('', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('a', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('abc', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('message digest', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('abcdefghijklmnopqrstuvwxyz', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
+SELECT digest('12345678901234567890123456789012345678901234567890123456789012345678901234567890', 'md5');
+ERROR:  Cannot use "md5": Cipher cannot be initialized
diff --git a/contrib/pgcrypto/expected/pgp-encrypt-md5.out b/contrib/pgcrypto/expected/pgp-encrypt-md5.out
new file mode 100644
index 0000000000..339e12a434
--- /dev/null
+++ b/contrib/pgcrypto/expected/pgp-encrypt-md5.out
@@ -0,0 +1,11 @@
+--
+-- PGP encrypt using MD5
+--
+select pgp_sym_decrypt(
+	pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=md5'),
+	'key', 'expect-s2k-digest-algo=md5');
+ pgp_sym_decrypt 
+-----------------
+ Secret.
+(1 row)
+
diff --git a/contrib/pgcrypto/expected/pgp-encrypt-md5_1.out b/contrib/pgcrypto/expected/pgp-encrypt-md5_1.out
new file mode 100644
index 0000000000..612ca1d19c
--- /dev/null
+++ b/contrib/pgcrypto/expected/pgp-encrypt-md5_1.out
@@ -0,0 +1,7 @@
+--
+-- PGP encrypt using MD5
+--
+select pgp_sym_decrypt(
+	pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=md5'),
+	'key', 'expect-s2k-digest-algo=md5');
+ERROR:  Unsupported digest algorithm
diff --git a/contrib/pgcrypto/expected/pgp-encrypt.out b/contrib/pgcrypto/expected/pgp-encrypt.out
index 77e45abe53..50cd3f6daa 100644
--- a/contrib/pgcrypto/expected/pgp-encrypt.out
+++ b/contrib/pgcrypto/expected/pgp-encrypt.out
@@ -121,14 +121,6 @@ NOTICE:  pgp_decrypt: unexpected s2k_count: expected 65000000 got 65011712
 (1 row)
 
 -- s2k digest change
-select pgp_sym_decrypt(
-	pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=md5'),
-	'key', 'expect-s2k-digest-algo=md5');
- pgp_sym_decrypt 
------------------
- Secret.
-(1 row)
-
 select pgp_sym_decrypt(
 		pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=sha1'),
 	'key', 'expect-s2k-digest-algo=sha1');
diff --git a/contrib/pgcrypto/meson.build b/contrib/pgcrypto/meson.build
index df7dd50dbc..4f62ea0af0 100644
--- a/contrib/pgcrypto/meson.build
+++ b/contrib/pgcrypto/meson.build
@@ -48,6 +48,7 @@ pgcrypto_regress = [
   'pgp-armor',
   'pgp-decrypt',
   'pgp-encrypt',
+  'pgp-encrypt-md5',
   'pgp-pubkey-decrypt',
   'pgp-pubkey-encrypt',
   'pgp-info',
diff --git a/contrib/pgcrypto/sql/pgp-encrypt-md5.sql b/contrib/pgcrypto/sql/pgp-encrypt-md5.sql
new file mode 100644
index 0000000000..201636c820
--- /dev/null
+++ b/contrib/pgcrypto/sql/pgp-encrypt-md5.sql
@@ -0,0 +1,7 @@
+--
+-- PGP encrypt using MD5
+--
+
+select pgp_sym_decrypt(
+	pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=md5'),
+	'key', 'expect-s2k-digest-algo=md5');
diff --git a/contrib/pgcrypto/sql/pgp-encrypt.sql b/contrib/pgcrypto/sql/pgp-encrypt.sql
index ed8b17776b..f67329c2c3 100644
--- a/contrib/pgcrypto/sql/pgp-encrypt.sql
+++ b/contrib/pgcrypto/sql/pgp-encrypt.sql
@@ -63,9 +63,6 @@ select pgp_sym_decrypt(
 	'key', 'expect-s2k-count=65000000');
 
 -- s2k digest change
-select pgp_sym_decrypt(
-	pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=md5'),
-	'key', 'expect-s2k-digest-algo=md5');
 select pgp_sym_decrypt(
 		pgp_sym_encrypt('Secret.', 'key', 's2k-digest-algo=sha1'),
 	'key', 'expect-s2k-digest-algo=sha1');