diff --git a/build-support-windows/Dockerfile-consul-dev-windows b/build-support-windows/Dockerfile-consul-dev-windows
index b97f630856ec..6f5489240826 100644
--- a/build-support-windows/Dockerfile-consul-dev-windows
+++ b/build-support-windows/Dockerfile-consul-dev-windows
@@ -17,9 +17,9 @@ COPY --from=envoy ["C:/Program Files/envoy/", "C:/envoy/"]
 RUN choco install openssl -yf
 RUN choco install jq -yf
 
+# Install Bats
 ENV BATS_URL=https://github.com/bats-core/bats-core/archive/refs/tags/v1.7.0.zip
 RUN curl %BATS_URL% -L -o bats.zip
-
 RUN mkdir bats-core
 RUN tar -xf bats.zip -C bats-core --strip-components=1
 RUN cd "C:\\Program Files\\Git\\bin" && bash.exe -c "/c/bats-core/install.sh /c/bats"
@@ -30,6 +30,9 @@ RUN curl %JAEGER_URL% -L -o jaeger.tar.gz
 RUN mkdir jaeger
 RUN tar -xf jaeger.tar.gz -C jaeger --strip-components=1
 
+# Copy test-sds-server binary and certs
+COPY --from=test-sds-server ["C:/go/src/", "C:/test-sds-server/"]
+
 EXPOSE 8300
 EXPOSE 8301 8301/udp 8302 8302/udp
 EXPOSE 8500 8600 8600/udp
diff --git a/test/integration/connect/envoy/Dockerfile-test-sds-server-windows b/test/integration/connect/envoy/Dockerfile-test-sds-server-windows
index a9328a26108b..5973757530d1 100644
--- a/test/integration/connect/envoy/Dockerfile-test-sds-server-windows
+++ b/test/integration/connect/envoy/Dockerfile-test-sds-server-windows
@@ -3,6 +3,6 @@ FROM golang:1.18.1-nanoserver-1809
 WORKDIR /go/src
 COPY ./ .
 
-RUN go build -v -o test-sds-server sds.go
+RUN go build -v -o test-sds-server.exe sds.go
 
-CMD ["/go/src/test-sds-server"]
+CMD ["test-sds-server.exe"]
diff --git a/test/integration/connect/envoy/helpers.windows.bash b/test/integration/connect/envoy/helpers.windows.bash
index ef2200c9e29b..ee3725efc4e2 100644
--- a/test/integration/connect/envoy/helpers.windows.bash
+++ b/test/integration/connect/envoy/helpers.windows.bash
@@ -155,7 +155,9 @@ function assert_cert_signed_by_ca {
   if [ -n "$SERVER_NAME" ]; then
     SNI_FLAG="-servername $SERVER_NAME"
   fi
-  CERT=$(openssl s_client -connect $HOSTPORT $SNI_FLAG -CAfile $CA_FILE -showcerts </dev/null)
+
+  # Fix in the CA_FILE parameter: for Windows environments, the root path starts with "/c"
+  CERT=$(openssl s_client -connect $HOSTPORT $SNI_FLAG -CAfile "/c/$CA_FILE" -showcerts </dev/null)
 
   echo "GOT CERT:"
   echo "$CERT"
@@ -255,7 +257,7 @@ function assert_envoy_network_rbac_policy_count {
 }
 
 function get_envoy_network_rbac_once {
-  local HOSTPORT=$1  
+  local HOSTPORT=$1
   run curl -s -f $HOSTPORT/config_dump
   [ "$status" -eq 0 ]
   echo "$output" | jq --raw-output '.configs[2].dynamic_listeners[].active_state.listener.filter_chains[0].filters[] | select(.name == "envoy.filters.network.rbac") | .typed_config'
@@ -887,7 +889,8 @@ function get_upstream_fortio_name {
   if [ "${HOST:0:8}" = "https://" ]; then
     HOST="${HOST:8}"
     PROTO="https://"
-    extra_args="${extra_args} --cacert /workdir/test-sds-server/certs/ca-root.crt"
+    # Fix in the CA_FILE parameter: for Windows environments, the root path starts with "/c"
+    extra_args="${extra_args} --cacert /c/workdir/test-sds-server/certs/ca-root.crt"
   fi
   # We use --resolve instead of setting a Host header since we need the right
   # name to be sent for SNI in some cases too.
@@ -905,7 +908,7 @@ function get_upstream_fortio_name {
 
 function assert_expected_fortio_name {
   local EXPECT_NAME=$1
-  local HOST=${2:-"localhost"} $2
+  local HOST=${2:-"localhost"}
   local PORT=${3:-5000}
   local URL_PREFIX=${4:-""}
   local DEBUG_HEADER_VALUE="${5:-""}"
diff --git a/test/integration/connect/envoy/run-tests.windows.sh b/test/integration/connect/envoy/run-tests.windows.sh
index 0db80b31d573..c7f5739f8f8f 100644
--- a/test/integration/connect/envoy/run-tests.windows.sh
+++ b/test/integration/connect/envoy/run-tests.windows.sh
@@ -557,10 +557,6 @@ function suite_setup {
         --net=none \
         "${HASHICORP_DOCKER_PROXY}/windows/kubernetes/pause" &>/dev/null
     # TODO(rb): switch back to "${HASHICORP_DOCKER_PROXY}/google/pause" once that is cached
-
-    # pre-build the test-sds-server container
-    echo "Rebuilding 'test-sds-server' image..."
-    docker.exe build -t test-sds-server -f Dockerfile-test-sds-server-windows test-sds-server
 }
 
 function suite_teardown {
@@ -811,6 +807,8 @@ function run_container_zipkin {
 }
 
 function run_container_jaeger {
+  echo "Starting Jaeger service..."
+
   local DC=${1:-primary}
   local CONTAINER_NAME="$SINGLE_CONTAINER_BASE_NAME"-"$DC"_1
 
@@ -819,10 +817,13 @@ function run_container_jaeger {
 }
 
 function run_container_test-sds-server {
-  docker.exe run -d --name $(container_name) \
-    $WORKDIR_SNIPPET \
-    $(network_snippet primary) \
-    "test-sds-server"
+  echo "Starting test-sds-server"
+  
+  local DC=${1:-primary}
+  local CONTAINER_NAME="$SINGLE_CONTAINER_BASE_NAME"-"$DC"_1
+
+  docker.exe exec -d $CONTAINER_NAME bash -c "cd /c/test-sds-server &&
+                                              ./test-sds-server.exe"
 }
 
 function container_name {