diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 1ad2aafe..0497589c 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -35,10 +35,10 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: cross-compiled-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
+          key: cross-compiled-v3-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
           restore-keys: |
-            cross-compiled-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
-            cross-compiled-${{ matrix.platform }}-
+            cross-compiled-v3-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
+            cross-compiled-v3-${{ matrix.platform }}-
 
       - name: Build gem
         shell: bash
@@ -351,10 +351,10 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: native-${{ hashFiles('**/.ports_versions') }}
+          key: native-v3-${{ hashFiles('**/.ports_versions') }}
           restore-keys: |
-            native-${{ hashFiles('* */.ports_versions') }}
-            native-
+            native-v3-${{ hashFiles('* */.ports_versions') }}
+            native-v3-
 
       - name: Build required libraries
         run: |
@@ -394,7 +394,7 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: native-${{ hashFiles('**/.ports_versions') }}
+          key: native-v3-${{ hashFiles('**/.ports_versions') }}
           fail-on-cache-miss: true
 
       - name: Build gem
diff --git a/CHANGELOG.md b/CHANGELOG.md
index f95deac6..9761fbbb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,7 +4,7 @@
 * Drop support for SQL Server < 2017
 * Drop support for FreeTDS < 1.0
 * Raise error if FreeTDS is unable to sent command buffer to the server
-* Use freetds v1.4.23 and libiconv v1.17 for Windows builds
+* Use freetds v1.4.23, libiconv v1.17 and OpenSSL v3.4.0 for Windows builds
 
 ## 2.1.7
 * Add Ruby 3.3 to the cross compile list
diff --git a/ext/tiny_tds/extconsts.rb b/ext/tiny_tds/extconsts.rb
index 19f9a133..64af1704 100644
--- a/ext/tiny_tds/extconsts.rb
+++ b/ext/tiny_tds/extconsts.rb
@@ -2,7 +2,7 @@
 ICONV_VERSION = ENV['TINYTDS_ICONV_VERSION'] || "1.17"
 ICONV_SOURCE_URI = "http://ftp.gnu.org/pub/gnu/libiconv/libiconv-#{ICONV_VERSION}.tar.gz"
 
-OPENSSL_VERSION = ENV['TINYTDS_OPENSSL_VERSION'] || '1.1.1s'
+OPENSSL_VERSION = ENV['TINYTDS_OPENSSL_VERSION'] || '3.4.0'
 OPENSSL_SOURCE_URI = "https://www.openssl.org/source/openssl-#{OPENSSL_VERSION}.tar.gz"
 
 FREETDS_VERSION = ENV['TINYTDS_FREETDS_VERSION'] || '1.4.23'
diff --git a/tasks/ports.rake b/tasks/ports.rake
index 451267f7..1ab6bf96 100644
--- a/tasks/ports.rake
+++ b/tasks/ports.rake
@@ -48,10 +48,10 @@ namespace :ports do
     if libraries_to_compile[:openssl]
       # freetds doesn't have an option that will provide an rpath
       # so we do it manually
-      ENV['OPENSSL_CFLAGS'] = "-Wl,-rpath -Wl,#{libraries_to_compile[:openssl].path}/lib"
+      ENV['OPENSSL_CFLAGS'] = "-Wl,-rpath -Wl,#{libraries_to_compile[:openssl].path}/lib64"
       # Add the pkgconfig file with MSYS2'ish path, to prefer our ports build
       # over MSYS2 system OpenSSL.
-      ENV['PKG_CONFIG_PATH'] = "#{libraries_to_compile[:openssl].path.gsub(/^(\w):/i) { "/" + $1.downcase }}/lib/pkgconfig:#{ENV['PKG_CONFIG_PATH']}"
+      ENV['PKG_CONFIG_PATH'] = "#{libraries_to_compile[:openssl].path.gsub(/^(\w):/i) { "/" + $1.downcase }}/lib64/pkgconfig:#{ENV['PKG_CONFIG_PATH']}"
       libraries_to_compile[:freetds].configure_options << "--with-openssl=#{libraries_to_compile[:openssl].path}"
     end