diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index a7539edc..cd0c8a29 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -12,7 +12,6 @@ jobs:
       matrix:
         platform:
           - "x64-mingw32"
-          - "x86-mingw32"
           - "x64-mingw-ucrt"
     name: cross-compile-windows
     runs-on: ubuntu-22.04
@@ -35,10 +34,10 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: cross-compiled-${{ hashFiles('**/.ports_versions') }}
+          key: cross-compiled-v3-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
           restore-keys: |
-            cross-compiled-${{ hashFiles('**/.ports_versions') }}
-            cross-compiled-v2-
+            cross-compiled-v3-${{ matrix.platform }}-${{ hashFiles('**/.ports_versions') }}
+            cross-compiled-v3-${{ matrix.platform }}-
 
       - name: Build gem
         shell: bash
@@ -96,8 +95,11 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
+        force-encryption:
+          - false
+          - true
         mssql-version:
-          #- 2017
+          - 2017
           - 2019
           - 2022
         ruby-version:
@@ -138,12 +140,12 @@ jobs:
           Copy-Item -Path ".\tmp\tiny_tds-$gemVersion-$rubyArchitecture\ports" -Destination "." -Recurse
 
       - name: Setup MSSQL
-        uses: potatoqualitee/mssqlsuite@v1.7
+        uses: rails-sqlserver/setup-mssql@v1
         with:
-          install: sqlengine, sqlclient
+          components: sqlcmd,sqlengine
           version: ${{ matrix.mssql-version }}
           sa-password: c0MplicatedP@ssword
-          show-log: true
+          force-encryption: ${{ matrix.force-encryption }}
 
       - name: Setup MSSQL database
         shell: pwsh
@@ -217,8 +219,11 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
+        force-encryption:
+          - false
+          - true
         mssql-version:
-          #- 2017
+          - 2017
           - 2019
           - 2022
         ruby-version:
@@ -259,12 +264,12 @@ jobs:
           Copy-Item -Path ".\tmp\tiny_tds-$gemVersion-$rubyArchitecture\ports" -Destination "." -Recurse
 
       - name: Setup MSSQL
-        uses: potatoqualitee/mssqlsuite@v1.7
+        uses: rails-sqlserver/setup-mssql@v1
         with:
-          install: sqlengine, sqlclient
+          components: sqlcmd,sqlengine
           version: ${{ matrix.mssql-version }}
           sa-password: c0MplicatedP@ssword
-          show-log: true
+          force-encryption: ${{ matrix.force-encryption }}
 
       - name: Setup MSSQL database
         shell: pwsh
@@ -345,10 +350,10 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: native-v2-${{ hashFiles('**/.ports_versions') }}
+          key: native-v3-${{ hashFiles('**/.ports_versions') }}
           restore-keys: |
-            native-${{ hashFiles('* */.ports_versions') }}
-            native-v2-
+            native-v3-${{ hashFiles('* */.ports_versions') }}
+            native-v3-
 
       - name: Build required libraries
         run: |
@@ -388,7 +393,7 @@ jobs:
         uses: actions/cache@v4
         with:
           path: ports
-          key: native-v2-${{ hashFiles('**/.ports_versions') }}
+          key: native-v3-${{ hashFiles('**/.ports_versions') }}
           fail-on-cache-miss: true
 
       - name: Build gem
@@ -396,12 +401,11 @@ jobs:
           bundle exec rake build
 
       - name: Setup MSSQL
-        uses: potatoqualitee/mssqlsuite@v1.7
+        uses: rails-sqlserver/setup-mssql@v1
         with:
-          install: sqlengine, sqlclient
+          components: sqlcmd,sqlengine
           version: ${{ matrix.mssql-version }}
           sa-password: "c0MplicatedP@ssword"
-          show-log: true
 
       - name: Setup MSSQL database
         run: |
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0c7e7ab5..14efc701 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,7 +3,9 @@
 * Drop support for Ruby < 2.7
 * Drop support for SQL Server < 2017
 * Drop support for FreeTDS < 1.0
+* No longer provide a 32-bit Windows build
 * Raise error if FreeTDS is unable to sent command buffer to the server
+* 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/README.md b/README.md
index 4aa68e69..de93787e 100644
--- a/README.md
+++ b/README.md
@@ -34,9 +34,9 @@ $ apt-get install wget
 $ apt-get install build-essential
 $ apt-get install libc6-dev
 
-$ wget http://www.freetds.org/files/stable/freetds-1.4.10.tar.gz
-$ tar -xzf freetds-1.4.10.tar.gz
-$ cd freetds-1.4.10
+$ wget http://www.freetds.org/files/stable/freetds-1.4.23.tar.gz
+$ tar -xzf freetds-1.4.23.tar.gz
+$ cd freetds-1.4.23
 $ ./configure --prefix=/usr/local --with-tdsver=7.4
 $ make
 $ make install
diff --git a/Rakefile b/Rakefile
index be8c60e6..f7580918 100644
--- a/Rakefile
+++ b/Rakefile
@@ -11,10 +11,6 @@ ruby_cc_ucrt_versions = "3.3.0:3.2.0:3.1.0".freeze
 ruby_cc_mingw32_versions = "3.0.0:2.7.0".freeze
 
 GEM_PLATFORM_HOSTS = {
-  'x86-mingw32' => {
-    host: 'i686-w64-mingw32',
-    ruby_versions: ruby_cc_mingw32_versions
-  },
   'x64-mingw32' => {
     host: 'x86_64-w64-mingw32',
     ruby_versions: ruby_cc_mingw32_versions
diff --git a/ext/tiny_tds/extconf.rb b/ext/tiny_tds/extconf.rb
index b1beabc4..d0691792 100644
--- a/ext/tiny_tds/extconf.rb
+++ b/ext/tiny_tds/extconf.rb
@@ -22,7 +22,6 @@ def do_help
 
 # Make sure to check the ports path for the configured host
 architecture = RbConfig::CONFIG['arch']
-architecture = "x86-mingw32" if architecture == "i386-mingw32"
 
 project_dir = File.expand_path("../../..", __FILE__)
 freetds_ports_dir = File.join(project_dir, 'ports', architecture, 'freetds', FREETDS_VERSION)
diff --git a/ext/tiny_tds/extconsts.rb b/ext/tiny_tds/extconsts.rb
index 0a362fa6..64af1704 100644
--- a/ext/tiny_tds/extconsts.rb
+++ b/ext/tiny_tds/extconsts.rb
@@ -1,9 +1,9 @@
 
-ICONV_VERSION = ENV['TINYTDS_ICONV_VERSION'] || "1.15"
+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'] || '1.1.24'
+FREETDS_VERSION = ENV['TINYTDS_FREETDS_VERSION'] || '1.4.23'
 FREETDS_SOURCE_URI = "http://www.freetds.org/files/stable/freetds-#{FREETDS_VERSION}.tar.bz2"
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
 
diff --git a/test/gem_test.rb b/test/gem_test.rb
index 48b7a631..b05a8edc 100644
--- a/test/gem_test.rb
+++ b/test/gem_test.rb
@@ -158,7 +158,6 @@ class GemTest < MiniTest::Spec
       {
         'x64-mingw-ucrt' => 'x64-mingw-ucrt',
         'x64-mingw32' => 'x64-mingw32',
-        'x86-mingw32' => 'x86-mingw32',
         'x86_64-linux' => 'x86_64-linux',
       }.each do |host,expected|
         describe "on a #{host} architecture" do