diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 83abaf89d126e6..cc79c9175b8caf 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -320,7 +320,7 @@ jobs:
         # Keep 1.1.1w in our list despite it being upstream EOL and otherwise
         # unsupported as it most resembles other 1.1.1-work-a-like ssl APIs
         # supported by important vendors such as AWS-LC.
-        openssl_ver: [1.1.1w, 3.0.17, 3.2.5, 3.3.4, 3.4.2, 3.5.2]
+        openssl_ver: [1.1.1w, 3.0.18, 3.2.6, 3.3.5, 3.4.3, 3.5.4]
         # See Tools/ssl/make_ssl_data.py for notes on adding a new version
     env:
       OPENSSL_VER: ${{ matrix.openssl_ver }}
@@ -410,7 +410,7 @@ jobs:
     needs: build-context
     if: needs.build-context.outputs.run-tests == 'true'
     env:
-      OPENSSL_VER: 3.0.16
+      OPENSSL_VER: 3.0.18
       PYTHONSTRICTEXTENSIONBUILD: 1
     steps:
     - uses: actions/checkout@v4
@@ -530,7 +530,7 @@ jobs:
       matrix:
         os: [ubuntu-24.04]
     env:
-      OPENSSL_VER: 3.0.16
+      OPENSSL_VER: 3.0.18
       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 76b19fd5d1a72e..7f8b9fdf5d6639 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: 3.0.15
+      OPENSSL_VER: 3.0.18
       PYTHONSTRICTEXTENSIONBUILD: 1
       TERM: linux
     steps:
diff --git a/Doc/using/configure.rst b/Doc/using/configure.rst
index 2cda9587975ddc..d5a329578ad833 100644
--- a/Doc/using/configure.rst
+++ b/Doc/using/configure.rst
@@ -22,7 +22,7 @@ Features and minimum versions required to build CPython:
 
 * Support for threads.
 
-* OpenSSL 1.1.1 is the minimum version and OpenSSL 3.0.16 is the recommended
+* OpenSSL 1.1.1 is the minimum version and OpenSSL 3.0.18 is the recommended
   minimum version for the :mod:`ssl` and :mod:`hashlib` extension modules.
 
 * SQLite 3.15.2 for the :mod:`sqlite3` extension module.
diff --git a/Modules/_ssl_data_35.h b/Modules/_ssl_data_35.h
index 9e69eaa910f003..e4919b550e3a89 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 2025-08-13T16:42:33.155822+00:00 */
-/* Generated from Git commit openssl-3.5.2-0-g0893a6235 */
+/* Generated on 2025-10-04T17:49:19.148321+00:00 */
+/* Generated from Git commit openssl-3.5.4-0-gc1eeb9406 */
 
 /* generated from args.lib2errnum */
 static struct py_ssl_library_code library_codes[] = {
@@ -5338,6 +5338,11 @@ static struct py_ssl_error_code error_codes[] = {
   #else
     {"FIPS_MODULE_ENTERING_ERROR_STATE", 57, 224},
   #endif
+  #ifdef PROV_R_FIPS_MODULE_IMPORT_PCT_ERROR
+    {"FIPS_MODULE_IMPORT_PCT_ERROR", ERR_LIB_PROV, PROV_R_FIPS_MODULE_IMPORT_PCT_ERROR},
+  #else
+    {"FIPS_MODULE_IMPORT_PCT_ERROR", 57, 253},
+  #endif
   #ifdef PROV_R_FIPS_MODULE_IN_ERROR_STATE
     {"FIPS_MODULE_IN_ERROR_STATE", ERR_LIB_PROV, PROV_R_FIPS_MODULE_IN_ERROR_STATE},
   #else
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index da21e7d97965d1..ab9840c1c5252d 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -48,11 +48,11 @@
 ]
 
 OPENSSL_RECENT_VERSIONS = [
-    "3.0.16",
-    "3.2.5",
-    "3.3.4",
-    "3.4.2",
-    "3.5.2",
+    "3.0.18",
+    "3.2.6",
+    "3.3.5",
+    "3.4.3",
+    "3.5.4",
     # See make_ssl_data.py for notes on adding a new version.
 ]