diff --git a/.azure-pipelines/ci.yml b/.azure-pipelines/ci.yml
index 12ff7d4c55c..fe10e45b679 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: 1.1.1c
+    openssl_version: 1.1.1d
 
   steps:
   - template: ./posix-steps.yml
@@ -116,7 +116,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1c
+    openssl_version: 1.1.1d
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.azure-pipelines/pr.yml b/.azure-pipelines/pr.yml
index e3e24ae2a4b..09209fc0c95 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: 1.1.1c
+    openssl_version: 1.1.1d
 
   steps:
   - template: ./posix-steps.yml
@@ -116,7 +116,7 @@ jobs:
   variables:
     testRunTitle: '$(Build.SourceBranchName)-linux-coverage'
     testRunPlatform: linux-coverage
-    openssl_version: 1.1.1c
+    openssl_version: 1.1.1d
 
   steps:
   - template: ./posix-steps.yml
diff --git a/.travis.yml b/.travis.yml
index 519dd9c6527..8a960c53426 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -11,7 +11,7 @@ cache:
 
 env:
   global:
-    - OPENSSL=1.1.1c
+    - OPENSSL=1.1.1d
     - OPENSSL_DIR="$HOME/multissl/openssl/${OPENSSL}"
     - PATH="${OPENSSL_DIR}/bin:$PATH"
     - CFLAGS="-I${OPENSSL_DIR}/include"
diff --git a/Misc/NEWS.d/next/Tests/2019-09-11-17-22-32.bpo-38117.X7LgGY.rst b/Misc/NEWS.d/next/Tests/2019-09-11-17-22-32.bpo-38117.X7LgGY.rst
new file mode 100644
index 00000000000..d3280375516
--- /dev/null
+++ b/Misc/NEWS.d/next/Tests/2019-09-11-17-22-32.bpo-38117.X7LgGY.rst
@@ -0,0 +1 @@
+Test with OpenSSL 1.1.1d
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index 7fda4df55a6..d816810d570 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -45,17 +45,16 @@ OPENSSL_OLD_VERSIONS = [
 ]
 
 OPENSSL_RECENT_VERSIONS = [
-    "1.0.2s",
-    "1.1.0k",
-    "1.1.1c",
+    "1.0.2t",
+    "1.1.0l",
+    "1.1.1d",
 ]
 
 LIBRESSL_OLD_VERSIONS = [
-    "2.9.2",
 ]
 
 LIBRESSL_RECENT_VERSIONS = [
-    "2.8.3",
+    "2.9.2",
 ]
 
 # store files in ../multissl