diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 8f71d8ed99ad4b..34060b2cd1d264 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -305,11 +305,11 @@ jobs:
           # unsupported as it most resembles other 1.1.1-work-a-like ssl APIs
           # supported by important vendors such as AWS-LC.
           - { name: openssl, version: 1.1.1w }
-          - { name: openssl, version: 3.0.19 }
-          - { name: openssl, version: 3.3.6 }
-          - { name: openssl, version: 3.4.4 }
-          - { name: openssl, version: 3.5.5 }
-          - { name: openssl, version: 3.6.1 }
+          - { name: openssl, version: 3.0.20 }
+          - { name: openssl, version: 3.3.7 }
+          - { name: openssl, version: 3.4.5 }
+          - { name: openssl, version: 3.5.6 }
+          - { name: openssl, version: 3.6.2 }
     env:
       SSLLIB_VER: ${{ matrix.ssllib.version }}
       MULTISSL_DIR: ${{ github.workspace }}/multissl
@@ -423,7 +423,7 @@ jobs:
     needs: build-context
     if: needs.build-context.outputs.run-ubuntu == 'true'
     env:
-      OPENSSL_VER: 3.0.18
+      OPENSSL_VER: 3.0.20
       PYTHONSTRICTEXTENSIONBUILD: 1
     steps:
     - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
@@ -531,7 +531,7 @@ jobs:
       matrix:
         os: [ubuntu-24.04]
     env:
-      OPENSSL_VER: 3.0.18
+      OPENSSL_VER: 3.0.20
       PYTHONSTRICTEXTENSIONBUILD: 1
       ASAN_OPTIONS: detect_leaks=0:allocator_may_return_null=1:handle_segv=0
     steps:
diff --git a/.github/workflows/reusable-ubuntu.yml b/.github/workflows/reusable-ubuntu.yml
index 40529cc86886f7..91f4ad4a40126b 100644
--- a/.github/workflows/reusable-ubuntu.yml
+++ b/.github/workflows/reusable-ubuntu.yml
@@ -30,7 +30,7 @@ jobs:
     runs-on: ${{ inputs.os }}
     timeout-minutes: 60
     env:
-      OPENSSL_VER: 3.0.18
+      OPENSSL_VER: 3.0.20
       PYTHONSTRICTEXTENSIONBUILD: 1
       TERM: linux
     steps:
diff --git a/Modules/_ssl_data_35.h b/Modules/_ssl_data_35.h
index 8a9fef87b2aec5..89c97f3be51a7f 100644
--- a/Modules/_ssl_data_35.h
+++ b/Modules/_ssl_data_35.h
@@ -1,6 +1,6 @@
 /* File generated by Tools/ssl/make_ssl_data.py */
-/* Generated on 2026-02-13T19:18:20.130102+00:00 */
-/* Generated from Git commit openssl-3.5.5-0-g67b5686b4 */
+/* Generated on 2026-05-03T20:36:01.807725+00:00 */
+/* Generated from Git commit openssl-3.5.6-0-g286ddeaac */
 
 /* generated from args.lib2errnum */
 static struct py_ssl_library_code library_codes[] = {
@@ -4248,6 +4248,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"CONNECT_FAILURE", 61, 100},
   #endif
+  #ifdef HTTP_R_CONTENT_TYPE_MISMATCH
+    {"CONTENT_TYPE_MISMATCH", ERR_LIB_HTTP, HTTP_R_CONTENT_TYPE_MISMATCH},
+  #else
+    {"CONTENT_TYPE_MISMATCH", 61, 131},
+  #endif
   #ifdef HTTP_R_ERROR_PARSING_ASN1_LENGTH
     {"ERROR_PARSING_ASN1_LENGTH", ERR_LIB_HTTP, HTTP_R_ERROR_PARSING_ASN1_LENGTH},
   #else
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index 86baf8a3a74bd4..85a8cd38f41bfa 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -49,11 +49,11 @@
 ]
 
 OPENSSL_RECENT_VERSIONS = [
-    "3.0.19",
-    "3.3.6",
-    "3.4.4",
-    "3.5.5",
-    "3.6.1",
+    "3.0.20",
+    "3.3.7",
+    "3.4.5",
+    "3.5.6",
+    "3.6.2",
     # See make_ssl_data.py for notes on adding a new version.
 ]