diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index 4e4f6c0b07..ec135060be 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -92,7 +92,7 @@ jobs:
           # TODO: maybe make the virtualenv a partial cache to exclude st2*?
           # !virtualenv/lib/python*/site-packages/st2*
           # !virtualenv/bin/st2*
-          key: ${{ runner.os }}-v2-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
+          key: ${{ runner.os }}-v3-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
           restore-keys: |
             ${{ runner.os }}-v2-python-${{ matrix.python }}-
       - name: Cache APT Dependencies
@@ -233,7 +233,7 @@ jobs:
           # TODO: maybe make the virtualenv a partial cache to exclude st2*?
           # !virtualenv/lib/python*/site-packages/st2*
           # !virtualenv/bin/st2*
-          key: ${{ runner.os }}-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
+          key: ${{ runner.os }}-v3-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
           restore-keys: |
             ${{ runner.os }}-python-${{ matrix.python }}-
       - name: Cache APT Dependencies
@@ -448,7 +448,7 @@ jobs:
           # TODO: maybe make the virtualenv a partial cache to exclude st2*?
           # !virtualenv/lib/python*/site-packages/st2*
           # !virtualenv/bin/st2*
-          key: ${{ runner.os }}-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
+          key: ${{ runner.os }}-v3-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
           restore-keys: |
             ${{ runner.os }}-python-${{ matrix.python }}-
       - name: Cache APT Dependencies
diff --git a/.github/workflows/orquesta-integration-tests.yaml b/.github/workflows/orquesta-integration-tests.yaml
index 98159afe8f..a7733b6512 100644
--- a/.github/workflows/orquesta-integration-tests.yaml
+++ b/.github/workflows/orquesta-integration-tests.yaml
@@ -139,7 +139,7 @@ jobs:
           # TODO: maybe make the virtualenv a partial cache to exclude st2*?
           # !virtualenv/lib/python*/site-packages/st2*
           # !virtualenv/bin/st2*
-          key: ${{ runner.os }}-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
+          key: ${{ runner.os }}-v3-python-${{ matrix.python-version }}-${{ hashFiles('requirements.txt', 'test-requirements.txt') }}
           restore-keys: |
             ${{ runner.os }}-python-${{ matrix.python }}-
       - name: Cache APT Dependencies
diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index 676df63b7d..8e07295e6d 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -45,6 +45,11 @@ Changed
 
   Contributed by Amanda McGuinness (@amanda11 Ammeon Solutions)
 
+* Pinned python module `networkx` to versions between 2.5.1(included) and 2.6(excluded) because Python v3.6 support was dropped in v2.6.
+  Also pinned `decorator==4.4.2` (dependency of `networkx<2.6`) to work around missing python 3.8 classifiers on `decorator`'s wheel. #5376
+
+  Contributed by @nzlosh
+
 Fixed
 ~~~~~
 
diff --git a/Makefile b/Makefile
index 018641bffd..e15bb11277 100644
--- a/Makefile
+++ b/Makefile
@@ -252,7 +252,7 @@ check-python-packages:
 	@echo ""
 	@echo "================== CHECK PYTHON PACKAGES ===================="
 	@echo ""
-	test -f $(VIRTUALENV_COMPONENTS_DIR)/bin/activate || virtualenv --python=$(PYTHON_VERSION) $(VIRTUALENV_COMPONENTS_DIR) --system-site-packages
+	test -f $(VIRTUALENV_COMPONENTS_DIR)/bin/activate || $(PYTHON_VERSION) -m venv $(VIRTUALENV_COMPONENTS_DIR) --system-site-packages
 	@for component in $(COMPONENTS_WITHOUT_ST2TESTS); do \
 		echo "==========================================================="; \
 		echo "Checking component:" $$component; \
@@ -268,7 +268,7 @@ check-python-packages-nightly:
 	@echo "================== CHECK PYTHON PACKAGES ===================="
 	@echo ""
 
-	test -f $(VIRTUALENV_COMPONENTS_DIR)/bin/activate || virtualenv --python=$(PYTHON_VERSION) $(VIRTUALENV_COMPONENTS_DIR) --no-download
+	test -f $(VIRTUALENV_COMPONENTS_DIR)/bin/activate || $(PYTHON_VERSION) -m venv $(VIRTUALENV_COMPONENTS_DIR)
 	@for component in $(COMPONENTS_WITHOUT_ST2TESTS); do \
 		echo "==========================================================="; \
 		echo "Checking component:" $$component; \
@@ -392,7 +392,7 @@ black: requirements .black-check
 	. $(VIRTUALENV_DIR)/bin/activate; black --check --config pyproject.toml pylint_plugins/*.py || exit 1;
 
 # Black task which reformats the code using black
-.PHONY: black-format
+.PHONY: black
 black: requirements .black-format
 
 .PHONY: .black-format
@@ -406,7 +406,7 @@ black: requirements .black-format
 		echo "Running black on" $$component; \
 		echo "==========================================================="; \
 		. $(VIRTUALENV_DIR)/bin/activate ; black --config pyproject.toml $$component/ || exit 1; \
-		. $(VIRTUALENV_DIR)/bin/activate ; black $$(grep -rl '^#!/.*python' $$component/bin) || exit 1; \
+		. $(VIRTUALENV_DIR)/bin/activate ; black --config pyproject.toml $$(grep -rl '^#!/.*python' $$component/bin) || exit 1; \
 	done
 	# runner modules and packages
 	@for component in $(COMPONENTS_RUNNERS); do\
@@ -414,7 +414,7 @@ black: requirements .black-format
 		echo "Running black on" $$component; \
 		echo "==========================================================="; \
 		. $(VIRTUALENV_DIR)/bin/activate ; black --config pyproject.toml  $$component/ || exit 1; \
-		. $(VIRTUALENV_DIR)/bin/activate ; black $$(grep -rl '^#!/.*python' $$component/bin) || exit 1; \
+		. $(VIRTUALENV_DIR)/bin/activate ; black --config pyproject.toml $$(grep -rl '^#!/.*python' $$component/bin) || exit 1; \
 	done
 	. $(VIRTUALENV_DIR)/bin/activate; black --config pyproject.toml contrib/ || exit 1;
 	. $(VIRTUALENV_DIR)/bin/activate; black --config pyproject.toml scripts/*.py || exit 1;
@@ -486,7 +486,7 @@ flake8: requirements .flake8
 	@echo
 	@echo "==================== st2client pypi check ===================="
 	@echo
-	test -f $(VIRTUALENV_ST2CLIENT_PYPI_DIR)/bin/activate || virtualenv --python=python3 $(VIRTUALENV_ST2CLIENT_PYPI_DIR) --no-download
+	test -f $(VIRTUALENV_ST2CLIENT_PYPI_DIR)/bin/activate || $(PYTHON_VERSION) -m venv $(VIRTUALENV_ST2CLIENT_PYPI_DIR)
 
 	# Setup PYTHONPATH in bash activate script...
 	# Delete existing entries (if any)
@@ -514,7 +514,7 @@ flake8: requirements .flake8
 	@echo
 	@echo "==================== st2client install check ===================="
 	@echo
-	test -f $(VIRTUALENV_ST2CLIENT_DIR)/bin/activate || virtualenv --python=$(PYTHON_VERSION) $(VIRTUALENV_ST2CLIENT_DIR) --no-download
+	test -f $(VIRTUALENV_ST2CLIENT_DIR)/bin/activate || $(PYTHON_VERSION) -m venv $(VIRTUALENV_ST2CLIENT_DIR)
 
 	# Setup PYTHONPATH in bash activate script...
 	# Delete existing entries (if any)
@@ -740,7 +740,7 @@ virtualenv:
 	@echo
 	@echo "==================== virtualenv ===================="
 	@echo
-	test -f $(VIRTUALENV_DIR)/bin/activate || virtualenv --python=$(PYTHON_VERSION) $(VIRTUALENV_DIR) --no-download
+	test -f $(VIRTUALENV_DIR)/bin/activate || $(PYTHON_VERSION) -m venv $(VIRTUALENV_DIR)
 
 	# Setup PYTHONPATH in bash activate script...
 	# Delete existing entries (if any)
diff --git a/OWNERS.md b/OWNERS.md
index 6ccccc305c..52431bf0fc 100644
--- a/OWNERS.md
+++ b/OWNERS.md
@@ -19,8 +19,6 @@ Senior [@StackStorm/maintainers](https://github.com/orgs/StackStorm/teams/mainta
 Have deep platform knowledge & experience and demonstrate technical leadership as well as driving the project forward.
 * Amanda McGuinness ([@amanda11](https://github.com/amanda11)), _Ammeon Solutions_ <<amanda.mcguinness@ammeonsolutions.com>>
   - Ansible, Core, deb/rpm packages, CI/CD, Deployments, Release Engineering, Infrastructure, Documentation.
-* blag ([@blag](https://github.com/blag)) <<blag@users.noreply.github.com>>
-  - ChatOps, StackStorm Exchange, Community, Documentation, CI/CD.
 * Eugen Cusmaunsa ([@armab](https://github.com/armab)) <<armab@stackstorm.com>>
   - Systems, Deployments, Docker, K8s, HA, Ansible, Chef, Vagrant, deb/rpm, CI/CD, Infrastructure, Release Engineering, Community.
 * Nick Maludy ([@nmaludy](https://github.com/nmaludy)) <<nmaludy@gmail.com>>
@@ -67,6 +65,8 @@ Thank you, Friends!
 * Anthony Shaw ([@tonybaloney](https://github.com/tonybaloney)) - Contribution via Ideas, Feedback, ChatOps improvements, core Architecture, Community and even [Marketing](https://news.ycombinator.com/item?id=14368748). [Case Study](https://stackstorm.com/case-study-dimension-data/).
 * Andy Moore ([@AndyMoore](https://github.com/AndyMoore)) - Community, StackStorm Exchange packs, Kubernetes.
 * Anirudh Rekhi ([@humblearner](https://github.com/humblearner)) - ex Stormer. Systems, CI/CD, DevOps, Infrastructure.
+* blag ([@blag](https://github.com/blag))
+  - ChatOps, StackStorm Exchange, Community, Documentation, CI/CD.
 * Denis Barishev ([@dennybaa](https://github.com/dennybaa)) - ex Stormer. Re-architeced StackStorm installer via deb/rpm packages, made it stable, repeatable, fixed first platform pain points.
 * Ed Medvedev ([@emedvedev](https://github.com/emedvedev)) - ex Stormer. Made WebUI slick and ChatOps awesome, discovered and implemented today's [StackStorm Exchange](https://exchange.stackstorm.org/).
 * Evan Powell ([@epowell101](https://github.com/epowell101)) - StackStorm co-founder, first CEO, Stormer forever.
diff --git a/contrib/runners/orquesta_runner/in-requirements.txt b/contrib/runners/orquesta_runner/in-requirements.txt
index 77570be456..770d7eaa07 100644
--- a/contrib/runners/orquesta_runner/in-requirements.txt
+++ b/contrib/runners/orquesta_runner/in-requirements.txt
@@ -1 +1 @@
-git+https://github.com/StackStorm/orquesta.git@219f00db5192321af9d29b4c51ec748846ab90c6#egg=orquesta
+git+https://github.com/StackStorm/orquesta.git@c971b94d5c3dc065ee18386bdf3609a3d2de4a2c#egg=orquesta
diff --git a/contrib/runners/orquesta_runner/requirements.txt b/contrib/runners/orquesta_runner/requirements.txt
index 03b03964bd..22ce5138bc 100644
--- a/contrib/runners/orquesta_runner/requirements.txt
+++ b/contrib/runners/orquesta_runner/requirements.txt
@@ -5,4 +5,4 @@
 # If you want to update depdencies for a single component, modify the
 # in-requirements.txt for that component and then run 'make requirements' to
 # update the component requirements.txt
-git+https://github.com/StackStorm/orquesta.git@219f00db5192321af9d29b4c51ec748846ab90c6#egg=orquesta
+git+https://github.com/StackStorm/orquesta.git@c971b94d5c3dc065ee18386bdf3609a3d2de4a2c#egg=orquesta
diff --git a/fixed-requirements.txt b/fixed-requirements.txt
index 2155f566fd..11648b1c10 100644
--- a/fixed-requirements.txt
+++ b/fixed-requirements.txt
@@ -22,8 +22,12 @@ jsonschema==2.6.0
 kombu==5.0.2
 lockfile==0.12.2
 mongoengine==0.23.0
-#Update networkx to match orquesta
-networkx>=2.5.1,<3.0
+# networkx v2.6 does not support Python3.6.  Update networkx to match orquesta
+networkx>=2.5.1,<2.6
+# networkx requires decorator>=4.3,<5 which should resolve to version 4.4.2
+# but the wheel on pypi does not say it supports python3.8, so pip gets
+# confused. For now, pin decorator to work around pip's confusion.
+decorator==4.4.2
 # NOTE: Recent version substantially affect the performance and add big import time overhead
 # See https://github.com/StackStorm/st2/issues/4160#issuecomment-394386433 for details
 oslo.config>=1.12.1,<1.13
diff --git a/requirements.txt b/requirements.txt
index 0c2438e1ca..c0693bb05f 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -12,11 +12,12 @@ argcomplete==1.12.2
 bcrypt==3.2.0
 chardet<3.1.0
 cryptography==3.4.7
+decorator==4.4.2
 dnspython>=1.16.0,<2.0.0
 eventlet==0.30.2
 flex==6.14.1
 git+https://github.com/StackStorm/logshipper.git@stackstorm_patched#egg=logshipper
-git+https://github.com/StackStorm/orquesta.git@219f00db5192321af9d29b4c51ec748846ab90c6#egg=orquesta
+git+https://github.com/StackStorm/orquesta.git@c971b94d5c3dc065ee18386bdf3609a3d2de4a2c#egg=orquesta
 git+https://github.com/StackStorm/st2-auth-backend-flat-file.git@master#egg=st2-auth-backend-flat-file
 git+https://github.com/StackStorm/st2-auth-ldap.git@master#egg=st2-auth-ldap
 git+https://github.com/StackStorm/st2-rbac-backend.git@master#egg=st2-rbac-backend
@@ -32,7 +33,7 @@ kombu==5.0.2
 lockfile==0.12.2
 mock==4.0.3
 mongoengine==0.23.0
-networkx>=2.5.1,<3.0
+networkx>=2.5.1,<2.6
 nose
 nose-parallel==0.4.0
 nose-timer==1.0.1
diff --git a/st2common/bin/st2ctl b/st2common/bin/st2ctl
index 9584efb4a7..4e2ff9a295 100755
--- a/st2common/bin/st2ctl
+++ b/st2common/bin/st2ctl
@@ -16,6 +16,7 @@
 
 COMPONENTS="st2actionrunner st2api st2stream st2auth st2garbagecollector st2notifier st2rulesengine st2sensorcontainer st2chatops st2timersengine st2workflowengine st2scheduler"
 ST2_CONF="/etc/st2/st2.conf"
+SYSTEMD_RELOADED=""
 
 # Ensure global environment is sourced if exists
 # Does not happen consistently with all OSes we support.
@@ -108,6 +109,11 @@ function service_manager() {
   local svcname=$1 action=$2
   if [ -d /run/systemd/system ]; then
     # systemd is running
+    if [ -z $SYSTEMD_RELOADED ]; then
+      #Reload systemd to regenerate socket files from st2.conf
+      systemctl daemon-reload
+      SYSTEMD_RELOADED="yes"
+    fi
     systemctl $action $svcname
   elif [ $(cat /proc/1/comm) = init ] && (/sbin/initctl version 2>/dev/null | grep -q upstart) &&
           [ -f /etc/init/${svcname}.conf ]; then
diff --git a/st2common/in-requirements.txt b/st2common/in-requirements.txt
index e32d20a07b..4e3579d1ed 100644
--- a/st2common/in-requirements.txt
+++ b/st2common/in-requirements.txt
@@ -10,7 +10,9 @@ jsonschema
 kombu
 mongoengine
 networkx
-git+https://github.com/StackStorm/orquesta.git@219f00db5192321af9d29b4c51ec748846ab90c6#egg=orquesta
+# used by networkx
+decorator
+git+https://github.com/StackStorm/orquesta.git@c971b94d5c3dc065ee18386bdf3609a3d2de4a2c#egg=orquesta
 git+https://github.com/StackStorm/st2-rbac-backend.git@master#egg=st2-rbac-backend
 oslo.config
 paramiko
diff --git a/st2common/requirements.txt b/st2common/requirements.txt
index 33ea04318a..b5d2745364 100644
--- a/st2common/requirements.txt
+++ b/st2common/requirements.txt
@@ -9,10 +9,11 @@ amqp==5.0.6
 apscheduler==3.7.0
 chardet<3.1.0
 cryptography==3.4.7
+decorator==4.4.2
 dnspython>=1.16.0,<2.0.0
 eventlet==0.30.2
 flex==6.14.1
-git+https://github.com/StackStorm/orquesta.git@219f00db5192321af9d29b4c51ec748846ab90c6#egg=orquesta
+git+https://github.com/StackStorm/orquesta.git@c971b94d5c3dc065ee18386bdf3609a3d2de4a2c#egg=orquesta
 git+https://github.com/StackStorm/st2-rbac-backend.git@master#egg=st2-rbac-backend
 gitdb==4.0.2
 gitpython==3.1.15
@@ -23,7 +24,7 @@ jsonschema==2.6.0
 kombu==5.0.2
 lockfile==0.12.2
 mongoengine==0.23.0
-networkx>=2.5.1,<3.0
+networkx>=2.5.1,<2.6
 orjson==3.5.2
 oslo.config>=1.12.1,<1.13
 paramiko==2.7.2