diff --git a/security/py-cryptography/Makefile b/security/py-cryptography/Makefile
index d0bd52c719e..6a48d26fac6 100644
--- a/security/py-cryptography/Makefile
+++ b/security/py-cryptography/Makefile
@@ -1,12 +1,11 @@
-# $OpenBSD: Makefile,v 1.34 2019/06/03 16:06:56 sthen Exp $
+# $OpenBSD: Makefile,v 1.35 2019/11/07 17:23:10 sthen Exp $
 
 COMMENT=	cryptographic recipes and primitives for Python
 
-MODPY_EGG_VERSION=	2.6.1
+MODPY_EGG_VERSION=	2.8
 DISTNAME=	cryptography-${MODPY_EGG_VERSION}
 PKGNAME=	${MODPY_PY_PREFIX}${DISTNAME}
 CATEGORIES=	security devel
-REVISION=	0
 
 HOMEPAGE=	https://cryptography.io/
 
@@ -39,8 +38,10 @@ RUN_DEPENDS+=	devel/py-enum34 \
 
 BUILD_DEPENDS=	${RUN_DEPENDS}
 
+MODPY_PYTEST=	Yes
 # XXX needs *loads* of RAM
-TEST_DEPENDS=	devel/py-coverage${MODPY_FLAVOR} \
+TEST_DEPENDS=	${FULLPKGNAME}:${FULLPKGPATH} \
+		devel/py-coverage${MODPY_FLAVOR} \
 		devel/py-hypothesis${MODPY_FLAVOR} \
 		devel/py-pretend${MODPY_FLAVOR} \
 		devel/py-test${MODPY_FLAVOR} \
diff --git a/security/py-cryptography/distinfo b/security/py-cryptography/distinfo
index 4787e75e2c8..075949763f0 100644
--- a/security/py-cryptography/distinfo
+++ b/security/py-cryptography/distinfo
@@ -1,2 +1,2 @@
-SHA256 (cryptography-2.6.1.tar.gz) = Jsghy+toP6y5ZgReIGQwMCnVcqh+5pylob9Uv1X5PKY=
-SIZE (cryptography-2.6.1.tar.gz) = 491580
+SHA256 (cryptography-2.8.tar.gz) = PNofDth0czm733G584ynTHtZLyT2XNs6s3ZeSwKHFlE=
+SIZE (cryptography-2.8.tar.gz) = 504516
diff --git a/security/py-cryptography/patches/patch-src__cffi_src_openssl_ssl_py b/security/py-cryptography/patches/patch-src__cffi_src_openssl_ssl_py
deleted file mode 100644
index 7a8e50bfd9d..00000000000
--- a/security/py-cryptography/patches/patch-src__cffi_src_openssl_ssl_py
+++ /dev/null
@@ -1,17 +0,0 @@
-$OpenBSD: patch-src__cffi_src_openssl_ssl_py,v 1.2 2019/04/19 10:18:16 sthen Exp $
-
-Index: src/_cffi_src/openssl/ssl.py
---- src/_cffi_src/openssl/ssl.py.orig
-+++ src/_cffi_src/openssl/ssl.py
-@@ -721,9 +721,11 @@ static const long TLS_ST_OK = 0;
- 
- #if CRYPTOGRAPHY_OPENSSL_LESS_THAN_102
- static const long Cryptography_HAS_GENERIC_DTLS_METHOD = 0;
-+#if !CRYPTOGRAPHY_IS_LIBRESSL
- const SSL_METHOD *(*DTLS_method)(void) = NULL;
- const SSL_METHOD *(*DTLS_server_method)(void) = NULL;
- const SSL_METHOD *(*DTLS_client_method)(void) = NULL;
-+#endif
- static const long SSL_OP_NO_DTLSv1 = 0;
- static const long SSL_OP_NO_DTLSv1_2 = 0;
- long (*DTLS_set_link_mtu)(SSL *, long) = NULL;
diff --git a/security/py-cryptography/pkg/PLIST b/security/py-cryptography/pkg/PLIST
index 0a9b90492b6..b2157bf77e9 100644
--- a/security/py-cryptography/pkg/PLIST
+++ b/security/py-cryptography/pkg/PLIST
@@ -1,4 +1,4 @@
-@comment $OpenBSD: PLIST,v 1.13 2019/04/19 10:18:16 sthen Exp $
+@comment $OpenBSD: PLIST,v 1.14 2019/11/07 17:23:10 sthen Exp $
 lib/python${MODPY_VERSION}/site-packages/cryptography/
 lib/python${MODPY_VERSION}/site-packages/cryptography-${MODPY_EGG_VERSION}-py${MODPY_VERSION}.egg-info/
 lib/python${MODPY_VERSION}/site-packages/cryptography-${MODPY_EGG_VERSION}-py${MODPY_VERSION}.egg-info/PKG-INFO
@@ -21,7 +21,9 @@ lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/__init__.py
 ${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/${MODPY_PYCACHE}/
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/${MODPY_PYCACHE}__init__.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/${MODPY_PYCACHE}_der.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/${MODPY_PYCACHE}_oid.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/_der.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/_oid.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/__init__.py
@@ -47,6 +49,7 @@ lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}hashes.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}hmac.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}ocsp.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}poly1305.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}rsa.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}utils.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/${MODPY_PYCACHE}x25519.${MODPY_PYC_MAGIC_TAG}pyc
@@ -66,6 +69,7 @@ lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/en
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/hashes.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/hmac.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/ocsp.py
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/poly1305.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/rsa.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/utils.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/backends/openssl/x25519.py
@@ -95,8 +99,8 @@ lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}hashes.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}hmac.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}keywrap.${MODPY_PYC_MAGIC_TAG}pyc
-lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}mac.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}padding.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/${MODPY_PYCACHE}poly1305.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/asymmetric/
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/asymmetric/__init__.py
 ${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/asymmetric/${MODPY_PYCACHE}/
@@ -154,8 +158,8 @@ lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/kdf/pbkd
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/kdf/scrypt.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/kdf/x963kdf.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/keywrap.py
-lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/mac.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/padding.py
+lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/poly1305.py
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/serialization/
 lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/serialization/__init__.py
 ${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/cryptography/hazmat/primitives/serialization/${MODPY_PYCACHE}/
diff --git a/security/py-cryptography_vectors/Makefile b/security/py-cryptography_vectors/Makefile
index 869a950949e..79177e472c5 100644
--- a/security/py-cryptography_vectors/Makefile
+++ b/security/py-cryptography_vectors/Makefile
@@ -1,12 +1,11 @@
-# $OpenBSD: Makefile,v 1.23 2019/06/03 16:06:56 sthen Exp $
+# $OpenBSD: Makefile,v 1.24 2019/11/07 17:23:10 sthen Exp $
 
 COMMENT=	test vectors for py-cryptography
 
-MODPY_EGG_VERSION=	2.6.1
+MODPY_EGG_VERSION=	2.8
 DISTNAME=	cryptography_vectors-${MODPY_EGG_VERSION}
 PKGNAME=	${MODPY_PY_PREFIX}${DISTNAME}
 CATEGORIES=	security
-REVISION=	0
 
 HOMEPAGE=	https://cryptography.io/
 
diff --git a/security/py-cryptography_vectors/distinfo b/security/py-cryptography_vectors/distinfo
index 25ba906da0b..11a4f82f1c7 100644
--- a/security/py-cryptography_vectors/distinfo
+++ b/security/py-cryptography_vectors/distinfo
@@ -1,2 +1,2 @@
-SHA256 (cryptography_vectors-2.6.1.tar.gz) = A/OBFdzLJm3ZZTj5QGdEKod5MsIyJmG9xb8lAsdmWK8=
-SIZE (cryptography_vectors-2.6.1.tar.gz) = 35097785
+SHA256 (cryptography_vectors-2.8.tar.gz) = bNMhdMVqPspy9kr0PB2qyq51jPpf+dKA38+Bj6Ee8RY=
+SIZE (cryptography_vectors-2.8.tar.gz) = 35102030
diff --git a/security/py-cryptography_vectors/pkg/PLIST b/security/py-cryptography_vectors/pkg/PLIST
index 6a0dcd535c7..3d40fb80a97 100644
--- a/security/py-cryptography_vectors/pkg/PLIST
+++ b/security/py-cryptography_vectors/pkg/PLIST
@@ -1,4 +1,4 @@
-@comment $OpenBSD: PLIST,v 1.12 2019/04/19 10:18:17 sthen Exp $
+@comment $OpenBSD: PLIST,v 1.13 2019/11/07 17:23:10 sthen Exp $
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors-${MODPY_EGG_VERSION}-py${MODPY_VERSION}.egg-info/
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors-${MODPY_EGG_VERSION}-py${MODPY_VERSION}.egg-info/PKG-INFO
@@ -38,6 +38,8 @@ lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Ser
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/dsa.2048.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/dsa.3072.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/dsa_public_key.der
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/dsa_public_key_invalid_bit_string.der
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/dsa_public_key_no_params.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/ec_private_key.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/ec_private_key_encrypted.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/asymmetric/DER_Serialization/ec_public_key.der
@@ -620,6 +622,8 @@ lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/pkcs12/cert-none-k
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/pkcs12/cert-rc2-key-3des.p12
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/pkcs12/no-cert-key-aes256cbc.p12
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/pkcs12/no-password.p12
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/poly1305/
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/poly1305/rfc7539.txt
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/twofactor/
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/twofactor/rfc-4226.txt
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/twofactor/rfc-6238.txt
@@ -2250,12 +2254,14 @@ lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/nc_per
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/nc_permitted_excluded.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/nc_permitted_excluded_2.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/nc_single_ip_netmask.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/negative_serial.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/ocsp_nocheck.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/pc_inhibit.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/pc_inhibit_require.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/pc_require.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/policy_constraints_explicit.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/post2000utctime.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/rsa_pss.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/san_dirname.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/san_email_dns_ip_dirname_uri.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/san_empty_hostname.pem
@@ -2279,6 +2285,13 @@ lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/custom/valid_
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/department-of-state-root.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/e-trust.ru.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ecdsa_root.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed25519/
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed25519/ed25519-rfc8410.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed25519/root-ed25519.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed25519/server-ed25519-cert.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed448/
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed448/root-ed448.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ed448/server-ed448-cert.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/letsencryptx3.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ocsp/
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ocsp/req-ext-nonce.der
@@ -2296,6 +2309,7 @@ lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/ocsp/resp-una
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/rapidssl_sha256_ca_g3.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/basic_constraints.pem
+lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/challenge.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/dsa_sha1.der
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/dsa_sha1.pem
 lib/python${MODPY_VERSION}/site-packages/cryptography_vectors/x509/requests/ec_sha256.der