diff --git a/.travis.yml b/.travis.yml
index 52131e8..2c120d2 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -1,5 +1,5 @@
-dist: trusty
-sudo: false
+dist: xenial
+sudo: true
 language: python
 
 cache:
@@ -15,13 +15,12 @@
   - language: generic
     os: osx
     osx_image: xcode10.1
-    env: TOXENV=py27
-  - language: generic
-    os: osx
-    osx_image: xcode10.1
-    env: TOXENV=py27 OPENSSL=1.1.0
+    env: TOXENV=py27 OPENSSL=1.1.1
   - python: "2.7" # these are just to make travis's UI a bit prettier
     env: TOXENV=py27
+    dist: trusty # For OpenSSL 1.0.1 coverage
+  - python: "2.7"
+    env: TOXENV=py27
   - python: "3.4"
     env: TOXENV=py34
   - python: "3.5"
@@ -30,11 +29,9 @@
     env: TOXENV=py36
   - python: "3.7"
     env: TOXENV=py37
-    dist: xenial
-    sudo: true
-  - python: "pypy"
+  - python: "pypy2.7-5.10.0"
     env: TOXENV=pypy
-  - python: "pypy3"
+  - python: "pypy3.5-5.10.1"
     env: TOXENV=pypy3
 
   # Also run the tests against cryptography master.
@@ -48,11 +45,9 @@
     env: TOXENV=py36-cryptographyMaster
   - python: "3.7"
     env: TOXENV=py37-cryptographyMaster
-    dist: xenial
-    sudo: true
-  - python: "pypy"
+  - python: "pypy2.7-5.10.0"
     env: TOXENV=pypy-cryptographyMaster
-  - python: "pypy3"
+  - python: "pypy3.5-5.10.1"
     env: TOXENV=pypy3-cryptographyMaster
 
   # And current minimum cryptography version.
@@ -66,11 +61,9 @@
     env: TOXENV=py36-cryptographyMinimum
   - python: "3.7"
     env: TOXENV=py37-cryptographyMinimum
-    dist: xenial
-    sudo: true
-  - python: "pypy"
+  - python: "pypy2.7-5.10.0"
     env: TOXENV=pypy-cryptographyMinimum
-  - python: "pypy3"
+  - python: "pypy3.5-5.10.1"
     env: TOXENV=pypy3-cryptographyMinimum
 
 
@@ -110,7 +103,7 @@
   - |
     if [[ "$(uname -s)" == 'Darwin' ]]; then
       brew update
-      if [[ "${OPENSSL}" == "1.1.0" ]]; then
+      if [[ "${OPENSSL}" == "1.1.1" ]]; then
         brew upgrade openssl@1.1
       else
         brew upgrade openssl
@@ -128,7 +121,7 @@
   - |
     if [[ "$(uname -s)" == 'Darwin' ]]; then
       # set our flags to use homebrew openssl
-      if [[ "${OPENSSL}"  == "1.1.0" ]]; then
+      if [[ "${OPENSSL}"  == "1.1.1" ]]; then
         export LDFLAGS="-L/usr/local/opt/openssl@1.1/lib"
         export CFLAGS="-I/usr/local/opt/openssl@1.1/include"
         export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"