diff --git a/test/images/echoserver/Dockerfile_windows b/test/images/echoserver/Dockerfile_windows
index 2b1ba96259a..708a59ce6a9 100644
--- a/test/images/echoserver/Dockerfile_windows
+++ b/test/images/echoserver/Dockerfile_windows
@@ -19,21 +19,24 @@ ARG REGISTRY
 FROM --platform=linux/amd64 alpine:3.6 as prep
 
 ADD https://openresty.org/download/openresty-1.13.6.2-win64.zip /openresty-win64.zip
+ADD http://wiki.overbyte.eu/arch/openssl-1.1.1i-win64.zip /openssl.zip
 RUN mkdir /openresty &&\
-    unzip /openresty-win64.zip -d /openresty
+    unzip /openresty-win64.zip -d /openresty &&\
+    mkdir /openssl &&\
+    unzip /openssl.zip -d /openssl
 
-FROM $REGISTRY/windows-image-builder-helper:1.1-windows-amd64-1809 as helper
 FROM $BASEIMAGE
 
 COPY --from=prep /openresty/openresty-1.13.6.2-win64 /openresty
-COPY --from=helper /Windows/System32/vcruntime140.dll /Windows/System32/
-COPY --from=helper ["/Program Files/OpenSSL", "/Program Files/OpenSSL"]
+COPY --from=prep /openssl /openssl
 
-ENV PATH="C:\openresty\;C:\bin\;C:\curl\;C:\Windows\system32;C:\Windows;C:\Program Files\PowerShell;"
+ADD ["https://raw.githubusercontent.com/openssl/openssl/OpenSSL_1_1_1i/apps/openssl.cnf", "/Program Files/Common Files/SSL/openssl.cnf"]
+
+ENV PATH="C:\openssl\;C:\openresty\;C:\bin\;C:\curl\;C:\Windows\system32;C:\Windows;C:\Program Files\PowerShell;"
 
 ADD run.sh /openresty/run.sh
 ADD nginx.conf /openresty/conf/nginx.conf
 ADD template.lua /openresty/lua/template.lua
 
 EXPOSE 80 443 8080 8443
-ENTRYPOINT ["/bin/sh", "/openresty/run.sh"]
+ENTRYPOINT ["/bin/sh", "-c", " cd /openresty && ./run.sh"]
diff --git a/test/images/echoserver/run.sh b/test/images/echoserver/run.sh
index 1f023cb98c8..1383b711f7b 100644
--- a/test/images/echoserver/run.sh
+++ b/test/images/echoserver/run.sh
@@ -21,5 +21,15 @@ openssl req -x509 -sha256 -nodes -days 365 -newkey rsa:2048 \
 -out /certs/certificate.crt \
 -subj "/C=UK/ST=Warwickshire/L=Leamington/O=OrgName/OU=IT Department/CN=example.com"
 
+# If we're running on Windows, skip loading the Linux .so modules.
+if [ "$(uname)" = "Windows_NT" ]; then
+	sed -i -E "s/^(load_module modules\/ndk_http_module.so;)$/#\1/" conf/nginx.conf
+	sed -i -E "s/^(load_module modules\/ngx_http_lua_module.so;)$/#\1/" conf/nginx.conf
+	sed -i -E "s/^(load_module modules\/ngx_http_lua_upstream_module.so;)$/#\1/" conf/nginx.conf
+
+	# NOTE(claudiub): on Windows, nginx will take the paths in the nginx.conf file as relative paths.
+	cmd /S /C "mklink /D C:\\openresty\\certs C:\\certs"
+fi
+
 echo "Starting nginx"
 nginx -g "daemon off;"