diff --git a/docs/changes/4.1.4.md b/docs/changes/4.1.4.md
index a3f7a68c4d..60ff28796a 100644
--- a/docs/changes/4.1.4.md
+++ b/docs/changes/4.1.4.md
@@ -33,7 +33,7 @@ Release date: `2019-xx-xx`
 
 ## Packaging / Build
 
-- [NXDRIVE-](https://jira.nuxeo.com/browse/NXDRIVE-): ...
+- [NXDRIVE-1224](https://jira.nuxeo.com/browse/NXDRIVE-1224): Upgrade from Python 3.6.8 to 3.7.3
 
 ## Tests
 
@@ -46,6 +46,8 @@ Release date: `2019-xx-xx`
 ## Minor Changes
 
 - Packaging: Added `junitparser` 1.3.2
+- Packaging: Added `requests` 2.2.0
+- Packaging: Removed `dataclasses` 0.6
 - Packaging: Updated `markdown` from 3.1 to 3.1.1
 - Packaging: Updated `nuxeo` from 2.0.5 to 2.1.1
 - Packaging: Updated `pre-commit` from 1.16.1 to 1.17.0
diff --git a/docs/support.md b/docs/support.md
index 2daa8bfaef..9d27c76ce5 100644
--- a/docs/support.md
+++ b/docs/support.md
@@ -60,10 +60,13 @@ If you want to use the module version as a basic module for your own software, p
 
 It may evolve quickly without notification as we are following the Python development cycle.
 
-As of now, we are using the __Python 3.6.8__.
+[//]: # (XXX_PYTHON)
+
+As of now, we are using the __Python 3.7.3__.
 
 History:
 
+- `2019-06-17` (v4.1.4): dropped support for Python 3.6
 - `2018-10-30` (v4.0.0): dropped support for Python 2.7
 - `2014-??-??`: dropped support for Python 2.6
 
diff --git a/requirements.txt b/requirements.txt
index fadb2e2a16..81780fa13d 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,5 +1,4 @@
 appdirs==1.4.3
-dataclasses==0.6
 distro==1.4.0; sys_platform == 'linux'
 https://github.com/GoodRx/universal-analytics-python/archive/77ce628c56de1ba51a9bf0774794fd687f785803.zip
 https://github.com/gorakhargosh/watchdog/archive/8b94506c3156a3b66faef7aac9a139f603772506.zip
@@ -16,8 +15,10 @@ pypac==0.12.0
 pypiwin32==223; sys_platform == 'win32'
 # Ignore PyQt5 updates until NXDRIVE-1391 is done
 PyQt5==5.11.2  # pyup: ignore
+# NXDRIVE-1560: issue with codesign on macOS and sip > 4.19.13
 PyQt5-sip==4.19.13
 python-dateutil==2.8.0
+requests==2.22.0
 rfc3987==1.3.8
 Send2Trash==1.5.0
 sentry-sdk==0.9.0
diff --git a/tests/__init__.py b/tests/__init__.py
index 975fb696c3..4f9e35fd18 100644
--- a/tests/__init__.py
+++ b/tests/__init__.py
@@ -18,7 +18,7 @@
 def _basename(path: str) -> str:
     """
     Patch shutil._basename for pathlib compatibility.
-    TODO: remove when https://bugs.python.org/issue32689 is fixed (Python 3.7.3 or newer)
+    TODO: remove when https://bugs.python.org/issue32689 is fixed (Python 3.7.4 or newer)
     """
     if isinstance(path, os.PathLike):
         return path.name
diff --git a/tools/posix/deploy_jenkins_slave.sh b/tools/posix/deploy_jenkins_slave.sh
index 6cb656191d..0a0a8a0032 100755
--- a/tools/posix/deploy_jenkins_slave.sh
+++ b/tools/posix/deploy_jenkins_slave.sh
@@ -87,7 +87,7 @@ check_import() {
 check_vars() {
     # Check required variables
     if [ "${PYTHON_DRIVE_VERSION:=unset}" = "unset" ]; then
-        export PYTHON_DRIVE_VERSION="3.6.8"  # XXX_PYTHON
+        export PYTHON_DRIVE_VERSION="3.7.3"  # XXX_PYTHON
     fi
     if [ "${WORKSPACE:=unset}" = "unset" ]; then
         echo "WORKSPACE not defined. Aborting."
@@ -131,9 +131,7 @@ check_vars() {
 install_deps() {
     echo ">>> Installing requirements"
     # Do not delete, it fixes "Could not import setuptools which is required to install from a source distribution."
-    ${PIP} setuptools
-    # NXDRIVE-1521: pip 19.0.1 prevents PyInstaller installation
-    ${PIP} pip==18.1
+    ${PIP} setuptools pip
     ${PIP} -r requirements.txt
     ${PIP} -r requirements-dev.txt
     if [ "${INSTALL_RELEASE_ARG:=0}" != "1" ]; then
diff --git a/tools/windows/deploy_jenkins_slave.ps1 b/tools/windows/deploy_jenkins_slave.ps1
index 3aca272bb8..edfeff6a73 100644
--- a/tools/windows/deploy_jenkins_slave.ps1
+++ b/tools/windows/deploy_jenkins_slave.ps1
@@ -173,7 +173,7 @@ function check_import($import) {
 function check_vars {
 	# Check required variables
 	if (-Not ($Env:PYTHON_DRIVE_VERSION)) {
-		$Env:PYTHON_DRIVE_VERSION = '3.6.8'  # XXX_PYTHON
+		$Env:PYTHON_DRIVE_VERSION = '3.7.3'  # XXX_PYTHON
 	} elseif (-Not ($Env:WORKSPACE)) {
 		Write-Output ">>> WORKSPACE not defined. Aborting."
 		ExitWithCode 1