diff --git a/.builders/images/windows-x86_64/Dockerfile b/.builders/images/windows-x86_64/Dockerfile
index 68dcd5e044e479..705a5f358617a6 100644
--- a/.builders/images/windows-x86_64/Dockerfile
+++ b/.builders/images/windows-x86_64/Dockerfile
@@ -95,6 +95,35 @@ RUN Get-RemoteFile `
     Remove-Item $Env:IBM_MQ_VERSION-IBM-MQC-Redist-Win64.zip; `
     setx /M MQ_FILE_PATH 'C:\ibm_mq'
 
+# Perl (to build OpenSSL)
+ENV PERL_VERSION="5.40.0.1"
+# RUN Get-RemoteFile `
+#       -Uri https://github.com/StrawberryPerl/Perl-Dist-Strawberry/releases/download/SP_54001_64bit_UCRT/strawberry-perl-$Env:PERL_VERSION-64bit.msi `
+#       -Path "C:\strawberry-perl-$Env:PERL_VERSION-64bit.msi" `
+#       -Hash '29f72c3403d316b5ec48204546a7aad6b5567ff9a346cacd94af81fe0ffdc83e' && `
+#     Get-ChildItem && `
+#     msiexec /i "C:\strawberry-perl-$Env:PERL_VERSION-64bit.msi" /quiet /qn /norestart && `
+#     Remove-Item "C:\strawberry-perl-$Env:PERL_VERSION-64bit.msi"
+RUN Get-RemoteFile `
+      -Uri https://github.com/StrawberryPerl/Perl-Dist-Strawberry/releases/download/SP_54001_64bit_UCRT/strawberry-perl-$Env:PERL_VERSION-64bit-portable.zip `
+      -Path "strawberry-perl-$Env:PERL_VERSION-64bit.zip" `
+    -Hash '754f3e2a8e473dc68d1540c7802fb166a025f35ef18960c4564a31f8b5933907' && `
+    7z x "strawberry-perl-$Env:PERL_VERSION-64bit.zip" -o "C:\perl" `
+    Remove-Item "strawberry-perl-$Env:PERL_VERSION-64bit.zip"
+
+# openssl
+ENV OPENSSL_VERSION="3.3.2"
+RUN Get-RemoteFile `
+      -Uri https://www.openssl.org/source/openssl-$Env:OPENSSL_VERSION.tar.gz `
+      -Path openssl-$Env:OPENSSL_VERSION.tar.gz `
+      -Hash '2e8a40b01979afe8be0bbfb3de5dc1c6709fedb46d6c89c10da114ab5fc3d281'; `
+    7z x openssl-$Env:OPENSSL_VERSION.tar.gz -r -y && `
+    7z x openssl-$Env:OPENSSL_VERSION.tar -oC:\openssl_3 && `
+    "C:\perl\perl\bin\perl.exe ./Configure" && `
+    make depend && `
+    make -j 4 && `
+    make install_sw
+
 # Set up runner
 COPY runner_dependencies.txt C:\runner_dependencies.txt
 RUN python -m pip install --no-warn-script-location -r C:\runner_dependencies.txt