diff --git a/Vagrantfile b/Vagrantfile
index 4659429e7..1427ccbba 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -97,13 +97,13 @@ def packages_darwin
     brew update > /dev/null
     brew install pkg-config
     brew install readline
-    brew install openssl
+    brew install openssl@1.1
     brew install zstd
     brew install lz4
     brew install xz  # required for python lzma module
     brew install fakeroot
     brew install git
-    echo 'export PKG_CONFIG_PATH=/usr/local/opt/openssl/lib/pkgconfig' >> ~vagrant/.bash_profile
+    echo 'export PKG_CONFIG_PATH=/usr/local/opt/openssl@1.1/lib/pkgconfig' >> ~vagrant/.bash_profile
   EOF
 end
 
@@ -126,10 +126,9 @@ end
 def install_pythons(boxname)
   return <<-EOF
     . ~/.bash_profile
-    pyenv install 3.7.0  # tests
-    pyenv install 3.6.0  # tests
-    pyenv install 3.5.3  # tests, 3.5.3 is first to support openssl 1.1<k
-    pyenv install 3.6.8  # binary build, use latest 3.6.x release
+    pyenv install 3.7.0  # tests, version supporting openssl 1.1
+    pyenv install 3.6.8  # binary build, tests, version supporting openssl 1.1
+    pyenv install 3.5.3  # tests, 3.5.3 is first to support openssl 1.1
     pyenv rehash
   EOF
 end
@@ -208,8 +207,8 @@ def run_tests(boxname)
     . ../borg-env/bin/activate
     if which pyenv 2> /dev/null; then
       # for testing, use the earliest point releases of the supported python versions:
-      pyenv global 3.5.3 3.6.0 3.7.0
-      pyenv local 3.5.3 3.6.0 3.7.0
+      pyenv global 3.5.3 3.6.8 3.7.0
+      pyenv local 3.5.3 3.6.8 3.7.0
     fi
     # otherwise: just use the system python
     if which fakeroot 2> /dev/null; then