diff --git a/UPDATING b/UPDATING
index 6570960f97f3..49e2fad6644a 100644
--- a/UPDATING
+++ b/UPDATING
@@ -5,6 +5,20 @@ they are unavoidable.
 You should get into the habit of checking this file for changes each time
 you update your ports collection, before attempting any port upgrades.
 
+20200428:
+  AFFECTS: users of sysutils/ansible
+  AUTHOR: bofh@FreeBSD.org
+
+  Ansible has been updated to 2.9.7. Please follow the porting guide
+  to update the rulesets:
+
+  https://docs.ansible.com/ansible/devel/porting_guides/porting_guide_2.9.html
+
+  If you wish to stay with 2.8 version, you can switch
+  to new sysutils/ansible28 port, which tracks stable 2.8 branch:
+
+  # pkg set -n ansible:ansible28
+
 20200428:
   AFFECTS: x11-servers/xwayland-devel
   AUTHOR: jbeich@FreeBSD.org
diff --git a/sysutils/Makefile b/sysutils/Makefile
index 9a513c90082c..ca32a94daaef 100644
--- a/sysutils/Makefile
+++ b/sysutils/Makefile
@@ -45,6 +45,7 @@
     SUBDIR += ansible25
     SUBDIR += ansible26
     SUBDIR += ansible27
+    SUBDIR += ansible28
     SUBDIR += anvil
     SUBDIR += apache-mesos
     SUBDIR += apachetop
diff --git a/sysutils/ansible/Makefile b/sysutils/ansible/Makefile
index b5c72bfc6d98..68fb34e52594 100644
--- a/sysutils/ansible/Makefile
+++ b/sysutils/ansible/Makefile
@@ -1,7 +1,7 @@
 # $FreeBSD$
 
 PORTNAME=	ansible
-PORTVERSION?=	2.8.11
+PORTVERSION?=	2.9.7
 PORTREVISION?=	0
 CATEGORIES=	sysutils python
 MASTER_SITES=	http://releases.ansible.com/ansible/
@@ -34,15 +34,47 @@ CONFLICTS?=	ansible1-* \
 		ansible25-* \
 		ansible27-* \
 		ansible26-* \
-		ansible27-*
+		ansible27-* \
+		ansible28-*
 
 EXTRA_PATCHES?=
 
 NO_ARCH=	yes
-USES?=		cpe python
+USES?=		cpe python shebangfix
 USE_PYTHON=	distutils autoplist concurrent
 CPE_VENDOR=	ansibleworks
 
+SHEBANG_FILES?=	\
+		test/lib/ansible_test/_data/injector/python.py \
+		test/lib/ansible_test/_data/versions.py \
+		test/lib/ansible_test/_data/virtualenvcheck.py \
+		test/lib/ansible_test/_data/yamlcheck.py \
+		test/lib/ansible_test/_data/cli/ansible_test_cli_stub.py \
+		test/lib/ansible_test/_data/sanity/import/importer.py \
+		test/lib/ansible_test/_data/sanity/code-smell/metaclass-boilerplate.py \
+		test/lib/ansible_test/_data/sanity/code-smell/future-import-boilerplate.py \
+		test/lib/ansible_test/_data/sanity/code-smell/use-argspec-type-path.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-get-exception.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-illegal-filenames.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-dict-iterkeys.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-smart-quotes.py \
+		test/lib/ansible_test/_data/sanity/code-smell/replace-urlopen.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-unicode-literals.py \
+		test/lib/ansible_test/_data/sanity/code-smell/action-plugin-docs.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-main-display.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-dict-itervalues.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-dict-iteritems.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-assert.py \
+		test/lib/ansible_test/_data/sanity/code-smell/use-compat-six.py \
+		test/lib/ansible_test/_data/sanity/code-smell/line-endings.py \
+		test/lib/ansible_test/_data/sanity/code-smell/symlinks.py \
+		test/lib/ansible_test/_data/sanity/code-smell/shebang.py \
+		test/lib/ansible_test/_data/sanity/code-smell/empty-init.py \
+		test/lib/ansible_test/_data/sanity/code-smell/no-basestring.py \
+		test/lib/ansible_test/_data/sanity/yamllint/yamllinter.py \
+		test/lib/ansible_test/_data/sanity/compile/compile.py \
+		test/lib/ansible_test/_data/sanity/validate-modules/main.py
+
 SUB_FILES=	pkg-message
 SUB_LIST+=	PYTHON_CMD=${PYTHON_CMD}
 
@@ -79,6 +111,8 @@ post-install-EXAMPLES-on:
 post-stage:
 	${FIND} ${STAGEDIR}${PREFIX}/bin -type l -name ansible-\* -lname ansible \
 		-execdir ${RLN} ansible-${PYTHON_VER} {} \;
+	# python autoplist doesn't add this file in plist
+	${RM} ${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}/ansible_test/_data/injector/ansible-inventory
 
 TEST_WRKSRC=${WRKSRC}/test
 
diff --git a/sysutils/ansible/distinfo b/sysutils/ansible/distinfo
index cbedf70bc368..42376a66557d 100644
--- a/sysutils/ansible/distinfo
+++ b/sysutils/ansible/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1587131533
-SHA256 (ansible-2.8.11.tar.gz) = 156caa8b6c60b9f0d5c7d57ee0f4e46d8e226147b58546be6a8ac52925a9c191
-SIZE (ansible-2.8.11.tar.gz) = 12712657
+TIMESTAMP = 1588106713
+SHA256 (ansible-2.9.7.tar.gz) = 7222ce925536a25b2912364e13b03a3e21dbf2f96799ebff304f48509324de7b
+SIZE (ansible-2.9.7.tar.gz) = 14215538
diff --git a/sysutils/ansible23/Makefile b/sysutils/ansible23/Makefile
index 60856f7c481e..8c5e2fbce443 100644
--- a/sysutils/ansible23/Makefile
+++ b/sysutils/ansible23/Makefile
@@ -1,7 +1,7 @@
 # $FreeBSD$
 
 PORTVERSION=	2.3.3.0
-PORTREVISION=	4
+PORTREVISION=	5
 PKGNAMESUFFIX=	23
 
 CONFLICTS=	ansible-* \
@@ -9,12 +9,14 @@ CONFLICTS=	ansible-* \
 		ansible24-* \
 		ansible25-* \
 		ansible26-* \
-		ansible27-*
+		ansible27-* \
+		ansible28-*
 
 MASTERDIR=	${.CURDIR}/../ansible
 DISTINFO_FILE=	${.CURDIR}/distinfo
 
 DEPRECATED=	Upstream support ended. Consider upgrading to sysutils/ansible
+EXPIRATION_DATE=2020-05-31
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}Jinja2>0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jmespath>0:devel/py-jmespath@${PY_FLAVOR} \
@@ -31,6 +33,7 @@ PLIST_FILES=	man/man1/ansible-console.1.gz \
 		man/man1/ansible-vault.1.gz \
 		man/man1/ansible.1.gz
 
+USES=		cpe python
 EXTRA_PATCHES=
 
 .include "${MASTERDIR}/Makefile"
diff --git a/sysutils/ansible24/Makefile b/sysutils/ansible24/Makefile
index fb572498e1cd..23b832e46f0e 100644
--- a/sysutils/ansible24/Makefile
+++ b/sysutils/ansible24/Makefile
@@ -1,7 +1,7 @@
 # $FreeBSD$
 
 PORTVERSION=	2.4.6.0
-PORTREVISION=	3
+PORTREVISION=	4
 PKGNAMESUFFIX=	24
 
 CONFLICTS=	ansible-* \
@@ -9,13 +9,16 @@ CONFLICTS=	ansible-* \
 		ansible23-* \
 		ansible25-* \
 		ansible26-* \
-		ansible27-*
+		ansible27-* \
+		ansible28-*
 
 MASTERDIR=	${.CURDIR}/../ansible
 DISTINFO_FILE=	${.CURDIR}/distinfo
 
 DEPRECATED=	Upstream support ended. Consider upgrading to sysutils/ansible
+EXPIRATION_DATE=2020-05-31
 
+USES=		cpe python
 EXTRA_PATCHES=
 
 .include "${MASTERDIR}/Makefile"
diff --git a/sysutils/ansible25/Makefile b/sysutils/ansible25/Makefile
index 91ab5468614d..c898414c79c0 100644
--- a/sysutils/ansible25/Makefile
+++ b/sysutils/ansible25/Makefile
@@ -1,7 +1,7 @@
 # $FreeBSD$
 
 PORTVERSION=	2.5.15
-PORTREVISION=	2
+PORTREVISION=	3
 PKGNAMESUFFIX=	25
 
 CONFLICTS=	ansible-* \
@@ -9,13 +9,16 @@ CONFLICTS=	ansible-* \
 		ansible23-* \
 		ansible24-* \
 		ansible26-* \
-		ansible27-*
+		ansible27-* \
+		ansible28-*
 
 MASTERDIR=	${.CURDIR}/../ansible
 DISTINFO_FILE=	${.CURDIR}/distinfo
 
 DEPRECATED=	Upstream support ended. Consider upgrading to sysutils/ansible
+EXPIRATION_DATE=2020-05-31
 
+USES=		cpe python
 EXTRA_PATCHES=
 
 .include "${MASTERDIR}/Makefile"
diff --git a/sysutils/ansible26/Makefile b/sysutils/ansible26/Makefile
index 90fb80318c7b..4971afc525fe 100644
--- a/sysutils/ansible26/Makefile
+++ b/sysutils/ansible26/Makefile
@@ -1,6 +1,7 @@
 # $FreeBSD$
 
 PORTVERSION=	2.6.20
+PORTREVISION=	1
 PKGNAMESUFFIX=	26
 
 CONFLICTS=	ansible-* \
@@ -8,13 +9,16 @@ CONFLICTS=	ansible-* \
 		ansible23-* \
 		ansible24-* \
 		ansible25-* \
-		ansible27-*
+		ansible27-* \
+		ansible28-*
 
 MASTERDIR=	${.CURDIR}/../ansible
 DISTINFO_FILE=	${.CURDIR}/distinfo
 
 DEPRECATED=	Upstream support ended. Consider upgrading to sysutils/ansible
+EXPIRATION_DATE=2020-05-31
 
+USES=		cpe python
 EXTRA_PATCHES=	${FILESDIR}/extra-patch-sesu
 
 .include "${MASTERDIR}/Makefile"
diff --git a/sysutils/ansible27/Makefile b/sysutils/ansible27/Makefile
index 93b3295fe7fc..73128123d341 100644
--- a/sysutils/ansible27/Makefile
+++ b/sysutils/ansible27/Makefile
@@ -1,6 +1,7 @@
 # $FreeBSD$
 
 PORTVERSION=	2.7.17
+PORTREVISION=	1
 PKGNAMESUFFIX=	27
 
 CONFLICTS=	ansible-* \
@@ -8,11 +9,13 @@ CONFLICTS=	ansible-* \
 		ansible23-* \
 		ansible24-* \
 		ansible25-* \
-		ansible26-*
+		ansible26-* \
+		ansible28-*
 
 MASTERDIR=	${.CURDIR}/../ansible
 DISTINFO_FILE=	${.CURDIR}/distinfo
 
+USES=		cpe python
 EXTRA_PATCHES=	${FILESDIR}/extra-patch-sesu \
 		${FILESDIR}/extra-patch-27
 
diff --git a/sysutils/ansible28/Makefile b/sysutils/ansible28/Makefile
new file mode 100644
index 000000000000..7467f8ecead2
--- /dev/null
+++ b/sysutils/ansible28/Makefile
@@ -0,0 +1,20 @@
+# $FreeBSD$
+
+PORTVERSION=	2.8.11
+PKGNAMESUFFIX=	28
+
+CONFLICTS=	ansible-* \
+		ansible1-* \
+		ansible23-* \
+		ansible24-* \
+		ansible25-* \
+		ansible26-* \
+		ansible27-*
+
+MASTERDIR=	${.CURDIR}/../ansible
+DISTINFO_FILE=	${.CURDIR}/distinfo
+
+USES=		cpe python
+EXTRA_PATCHES=
+
+.include "${MASTERDIR}/Makefile"
diff --git a/sysutils/ansible28/distinfo b/sysutils/ansible28/distinfo
new file mode 100644
index 000000000000..0d8078ab01ea
--- /dev/null
+++ b/sysutils/ansible28/distinfo
@@ -0,0 +1,3 @@
+TIMESTAMP = 1588106665
+SHA256 (ansible-2.8.11.tar.gz) = 156caa8b6c60b9f0d5c7d57ee0f4e46d8e226147b58546be6a8ac52925a9c191
+SIZE (ansible-2.8.11.tar.gz) = 12712657