diff --git a/README.md b/README.md
index 3b1878d..2cdee9e 100644
--- a/README.md
+++ b/README.md
@@ -387,8 +387,8 @@ environment active when using a shell at (or below) that location.
 zcash-gitian % pip3 install --upgrade pip
 Collecting pip
 [...]
-      Successfully uninstalled pip-20.0.2
-Successfully installed pip-20.1
+      Successfully uninstalled pip-20.1
+Successfully installed pip-20.1.1
 ```
 
 
@@ -407,7 +407,7 @@ Check that you can run `ansible` from the command line:
 
 ```
 zcash-gitian % ansible --version
-ansible 2.9.7
+ansible 2.9.9
 [...]
 zcash-gitian %
 ```
diff --git a/dependency_install_steps_by_platform/macOS.md b/dependency_install_steps_by_platform/macOS.md
index 971422f..b0b8a61 100644
--- a/dependency_install_steps_by_platform/macOS.md
+++ b/dependency_install_steps_by_platform/macOS.md
@@ -2,7 +2,7 @@
 
 This document assumes you are starting from a fresh install of macOS.
 
-Most recently tested 2020-04-22 with the following macOS release:
+Most recently tested 2020-05-27 with the following macOS release:
 
 ```
 % sw_vers
@@ -46,13 +46,13 @@ $ brew upgrade <formula name>
 
 Homebrew has a search page you can use to look up formula names: http://formulae.brew.sh/
 
-Most recently tested 2020-05-06 with the following Homebrew release:
+Most recently tested 2020-05-27 with the following Homebrew release:
 
 ```
 % brew --version
-Homebrew 2.2.15
-Homebrew/homebrew-core (git revision cb163; last commit 2020-05-06)
-Homebrew/homebrew-cask (git revision 25cbd; last commit 2020-05-06)
+Homebrew 2.2.17
+Homebrew/homebrew-core (git revision 376d; last commit 2020-05-27)
+Homebrew/homebrew-cask (git revision 7605d51; last commit 2020-05-27)
 ```
 
 That last line about "homebrew-cask" refers to a subcommand 'cask' that can manage the types of
@@ -72,7 +72,7 @@ that, the second attempt should succeed.
 $ brew cask install virtualbox
 ```
 
-Most recently tested 2020-05-06 with the following Virtualbox release:
+Most recently tested 2020-05-27 with the following Virtualbox release:
 
 ```
 % VBoxManage --version
@@ -87,11 +87,11 @@ Most recently tested 2020-05-06 with the following Virtualbox release:
 $ brew cask install vagrant
 ```
 
-Most recently tested 2020-05-06 with the following Vagrant release:
+Most recently tested 2020-05-27 with the following Vagrant release:
 
 ```
 % vagrant --version
-Vagrant 2.2.8
+Vagrant 2.2.9
 ```
 
 
@@ -102,7 +102,7 @@ Vagrant 2.2.8
 $ brew install gnupg
 ```
 
-Most recently tested 2020-05-06 with the following GnuPG release:
+Most recently tested 2020-05-27 with the following GnuPG release:
 
 ```
 % gpg --version
@@ -125,7 +125,7 @@ $ brew install python
 Note that to run python 3.x you need to use the name `python3`; running `python` will run python
 2.x.
 
-Most recently tested 2020-05-06 with the following Python release:
+Most recently tested 2020-05-27 with the following Python release:
 
 ```
 % python3 --version
@@ -162,9 +162,9 @@ _direnv_hook;[...]
 direnv also supports several other shells -- zsh, fish, tcsh, and elvish as of this writing. Its
 website includes instructions for enabling each of the shells it supports.
 
-Most recently tested 2020-05-06 with the following direnv release:
+Most recently tested 2020-05-27 with the following direnv release:
 
 ```
 % direnv --version
-2.21.2
+2.21.3
 ```
diff --git a/requirements-pip.lock b/requirements-pip.lock
index c30c639..203e1e6 100644
--- a/requirements-pip.lock
+++ b/requirements-pip.lock
@@ -1,6 +1,6 @@
 # Primary Dependencies
 # (Packages we actually decided to include)
-ansible==2.9.7
+ansible==2.9.9
 # Secondary Dependencies
 # (pulled in by one or more of the above dependencies)
 cffi==1.14.0
@@ -9,4 +9,4 @@ Jinja2==2.11.2
 MarkupSafe==1.1.1
 pycparser==2.20
 PyYAML==5.3.1
-six==1.14.0
+six==1.15.0