diff --git a/.azure-pipelines/ci.yml b/.azure-pipelines/ci.yml
index 15a83dd0370e19..1576599379c489 100644
--- a/.azure-pipelines/ci.yml
+++ b/.azure-pipelines/ci.yml
@@ -59,7 +59,7 @@ jobs:
   variables:
     testRunTitle: '$(build.sourceBranchName)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.0j
+    openssl_version: 1.1.1b
 
   steps:
   - template: ./posix-steps.yml
@@ -116,7 +116,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.0j
+    openssl_version: 1.1.1b
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.azure-pipelines/pr.yml b/.azure-pipelines/pr.yml
index 0bd7921bcbefcc..a95d60e4ba9a9a 100644
--- a/.azure-pipelines/pr.yml
+++ b/.azure-pipelines/pr.yml
@@ -59,7 +59,7 @@ jobs:
   variables:
     testRunTitle: '$(system.pullRequest.TargetBranch)-linux'
     testRunPlatform: linux
-    openssl_version: 1.1.0j
+    openssl_version: 1.1.1b
 
   steps:
   - template: ./posix-steps.yml
@@ -116,7 +116,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.0j
+    openssl_version: 1.1.1b
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.travis.yml b/.travis.yml
index c6e009291a2d9a..516fc98a4d7416 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -12,7 +12,7 @@ cache:
 
 env:
   global:
-    - OPENSSL=1.1.0i
+    - OPENSSL=1.1.1b
     - OPENSSL_DIR="$HOME/multissl/openssl/${OPENSSL}"
     - PATH="${OPENSSL_DIR}/bin:$PATH"
     # Use -O3 because we don't use debugger on Travis-CI
diff --git a/Misc/NEWS.d/next/Library/2019-02-28-17-08-47.bpo-34631.KgLT8q.rst b/Misc/NEWS.d/next/Library/2019-02-28-17-08-47.bpo-34631.KgLT8q.rst
new file mode 100644
index 00000000000000..43aaa2b4975387
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2019-02-28-17-08-47.bpo-34631.KgLT8q.rst
@@ -0,0 +1 @@
+Update test infrastructure to use OpenSSL 1.1.1b