diff --git a/.github/CONTRIBUTING.md b/.github/CONTRIBUTING.md
index 879d1c61c..292dcd86f 100644
--- a/.github/CONTRIBUTING.md
+++ b/.github/CONTRIBUTING.md
@@ -105,6 +105,10 @@ You may have noticed we have a `Makefile` and a `make.bat` in the top-level dire
 3. `make newenv`: Set up a new virtual environment in the `.venv` subdirectory, and install Red and its dependencies. If one already exists, it is cleared out and replaced.
 4. `make syncenv`: Sync your environment with Red's latest dependencies.
 
+The other make recipes are most likely for project maintainers rather than contributors.
+
+You can specify the Python executable used in the make recipes with the `PYTHON` environment variable, e.g. `make PYTHON=/usr/bin/python3.7 newenv`.
+
 ### 4.5 Keeping your dependencies up to date
 Whenever you pull from upstream (V3/develop on the main repository) and you notice either of the files `setup.cfg` or `tools/dev-requirements.txt` have been changed, it can often mean some package dependencies have been updated, added or removed. To make sure you're testing and formatting with the most up-to-date versions of our dependencies, run `make syncenv`. You could also simply do `make newenv` to install them to a clean new virtual environment.
 
diff --git a/Makefile b/Makefile
index c6f92b713..7ae79fedd 100644
--- a/Makefile
+++ b/Makefile
@@ -1,12 +1,14 @@
+PYTHON ?= python3.7
+
 # Python Code Style
 reformat:
-	black -l 99 --target-version py37 `git ls-files "*.py"`
+	$(PYTHON) -m black -l 99 --target-version py37 `git ls-files "*.py"`
 stylecheck:
-	black --check -l 99 --target-version py37 `git ls-files "*.py"`
+	$(PYTHON) -m black --check -l 99 --target-version py37 `git ls-files "*.py"`
 
 # Translations
 gettext:
-	redgettext --command-docstrings --verbose --recursive redbot --exclude-files "redbot/pytest/**/*"
+	$(PYTHON) -m redgettext --command-docstrings --verbose --recursive redbot --exclude-files "redbot/pytest/**/*"
 upload_translations:
 	$(MAKE) gettext
 	crowdin upload sources
@@ -15,11 +17,11 @@ download_translations:
 
 # Dependencies
 bumpdeps:
-	python tools/bumpdeps.py
+	$(PYTHON) tools/bumpdeps.py
 
 # Development environment
 newenv:
-	python3.7 -m venv --clear .venv
+	$(PYTHON) -m venv --clear .venv
 	.venv/bin/pip install -U pip setuptools
 	$(MAKE) syncenv
 syncenv:
@@ -28,4 +30,4 @@ syncenv:
 # Changelog check
 checkchangelog:
 	bash tools/check_changelog_entries.sh
-	python -m towncrier --draft
+	$(PYTHON) -m towncrier --draft
diff --git a/changelog.d/2939.misc.1.rst b/changelog.d/2939.misc.1.rst
new file mode 100644
index 000000000..1fd5f21b4
--- /dev/null
+++ b/changelog.d/2939.misc.1.rst
@@ -0,0 +1 @@
+Updated dependencies, most notably PyYAML, tqdm, uvloop and pymongo.
diff --git a/changelog.d/2939.misc.2.rst b/changelog.d/2939.misc.2.rst
new file mode 100644
index 000000000..b67b15a5e
--- /dev/null
+++ b/changelog.d/2939.misc.2.rst
@@ -0,0 +1 @@
+Setting the ``PYTHON`` env var whilst running ``make`` now allows you to specify which python executable to use.
diff --git a/setup.cfg b/setup.cfg
index 3579342c5..8b653ed99 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -31,7 +31,7 @@ install_requires =
     appdirs==1.4.3
     async-timeout==3.0.1
     attrs==19.1.0
-    babel==2.7.0
+    Babel==2.7.0
     chardet==3.0.4
     Click==7.0
     colorama==0.4.1
@@ -42,31 +42,31 @@ install_requires =
     idna==2.8
     multidict==4.5.2
     python-Levenshtein-wheels==0.13.1
-    PyYAML==5.1.1
+    pytz==2019.2
+    PyYAML==5.1.2
     Red-Lavalink==0.3.0
     schema==0.7.0
-    tqdm==4.32.2
-    uvloop==0.12.2; sys_platform != "win32" and platform_python_implementation == "CPython"
+    tqdm==4.35.0
+    uvloop==0.13.0; sys_platform != "win32" and platform_python_implementation == "CPython"
     websockets==6.0
     yarl==1.3.0
 
 [options.extras_require]
 docs =
     alabaster==0.7.12
-    Babel==2.7.0
     certifi==2019.6.16
-    docutils==0.14
+    docutils==0.15.2
     imagesize==1.1.0
+    incremental==17.5.0
     Jinja2==2.10.1
     MarkupSafe==1.1.1
-    packaging==19.0
+    packaging==19.1
     Pygments==2.4.2
-    pyparsing==2.4.0
-    pytz==2019.1
+    pyparsing==2.4.2
     requests==2.22.0
     six==1.12.0
     snowballstemmer==1.9.0
-    Sphinx==2.1.2
+    Sphinx==2.2.0
     sphinx-rtd-theme==0.4.3
     sphinxcontrib-applehelp==1.0.1
     sphinxcontrib-devhelp==1.0.1
@@ -75,12 +75,13 @@ docs =
     sphinxcontrib-qthelp==1.0.2
     sphinxcontrib-serializinghtml==1.1.3
     sphinxcontrib-trio==1.1.0
+    toml==0.10.0
     towncrier==19.2.0
     urllib3==1.25.3
 mongo =
     dnspython==1.16.0
     motor==2.0.0
-    pymongo==3.8.0
+    pymongo==3.9.0
 postgres =
     asyncpg==0.18.3
 style =
@@ -89,23 +90,23 @@ style =
 test =
     astroid==2.2.5
     atomicwrites==1.3.0
-    importlib-metadata==0.18
+    importlib-metadata==0.19
     isort==4.3.21
-    lazy-object-proxy==1.4.1
+    lazy-object-proxy==1.4.2
     mccabe==0.6.1
-    more-itertools==7.1.0
-    packaging==19.0
+    more-itertools==7.2.0
+    packaging==19.1
     pluggy==0.12.0
     py==1.8.0
     pylint==2.3.1
-    pyparsing==2.4.0
-    pytest==5.0.0
+    pyparsing==2.4.2
+    pytest==5.1.2
     pytest-asyncio==0.10.0
     six==1.12.0
     typed-ast==1.4.0
     wcwidth==0.1.7
     wrapt==1.11.2
-    zipp==0.5.1
+    zipp==0.6.0
 
 [options.entry_points]
 console_scripts =