diff --git a/test/integration/connect/envoy/helpers.windows.bash b/test/integration/connect/envoy/helpers.windows.bash
index 76934cb5bd5d..3d78c2bbcf2b 100644
--- a/test/integration/connect/envoy/helpers.windows.bash
+++ b/test/integration/connect/envoy/helpers.windows.bash
@@ -610,10 +610,9 @@ function kill_envoy {
   local BOOTSTRAP_NAME=$1
   local DC=${2:-primary}
 
-
   PORT=$( cat /c/workdir/$DC/envoy/${BOOTSTRAP_NAME}-bootstrap.json | jq .admin.address.socket_address.port_value )
   PID=$( netstat -qo | grep "127.0.0.1:$PORT" | sed -r "s/.* //g" )
-  KILL=$( tskill $PID )
+  tskill $PID
 }
 
 function must_match_in_statsd_logs {
@@ -853,7 +852,8 @@ function get_ca_root {
 function wait_for_agent_service_register {
   local SERVICE_ID=$1
   local DC=${2:-primary}
-  retry_default docker_curl "$DC" -sLf "http://consul-${DC}:8500/v1/agent/service/${SERVICE_ID}" >/dev/null
+
+  retry_default docker_consul_exec "$DC" bash -c "curl -sLf 'http://consul-${DC}:8500/v1/agent/service/${SERVICE_ID}' >/dev/null"
 }
 
 function set_ttl_check_state {
@@ -873,7 +873,7 @@ function set_ttl_check_state {
       return 1
   esac
 
-  retry_default docker_curl "${DC}" -sL -XPUT "http://consul-${DC}:8500/v1/agent/check/warn/${CHECK_ID}"
+  retry_default docker_consul_exec "$DC" bash -c "curl -sL -XPUT 'http://consul-${DC}:8500/v1/agent/check/warn/${CHECK_ID}' >/dev/null"
 }
 
 function get_upstream_fortio_name {
diff --git a/test/integration/connect/envoy/run-tests.windows.sh b/test/integration/connect/envoy/run-tests.windows.sh
index 1dd1fa71ef5c..45fd7086bb49 100644
--- a/test/integration/connect/envoy/run-tests.windows.sh
+++ b/test/integration/connect/envoy/run-tests.windows.sh
@@ -77,6 +77,7 @@ function init_workdir {
   # don't wipe logs between runs as they are already split and we need them to
   # upload as artifacts later.
   rm -rf workdir/${CLUSTER}
+  rm -rf workdir/logs
   mkdir -p workdir/${CLUSTER}/{consul,consul-server,register,envoy,bats,statsd,data}
 
   # Reload consul config from defaults
@@ -451,12 +452,12 @@ function stop_and_copy_files {
     # Create CMD file to execute within the container
     echo "XCOPY C:\workdir_bak C:\workdir /e /h /c /i /y" > copy.cmd
     # Stop dummy container to copy local workdir to container's workdir_bak
-    docker.exe stop envoy_workdir_1
+    docker.exe stop envoy_workdir_1 > /dev/null
     docker.exe cp workdir/. envoy_workdir_1:/workdir_bak
     # Copy CMD file into container
     docker.exe cp copy.cmd envoy_workdir_1:/
     # Start dummy container and execute the CMD file
-    docker.exe start envoy_workdir_1
+    docker.exe start envoy_workdir_1 > /dev/null
     docker.exe exec envoy_workdir_1 copy.cmd
     # Delete local CMD file after execution
     rm copy.cmd
@@ -470,7 +471,7 @@ function run_tests {
 
   init_vars
 
-  # Initialize the workdir
+  echo "Initialize the workdir"
   init_workdir primary
 
   if is_set $REQUIRE_SECONDARY
@@ -494,12 +495,13 @@ function run_tests {
     return 0
   fi
 
-  # Wipe state
+  echo "Wipe volumes"
   wipe_volumes
 
-  # Use this function to populate the shared volume
+  echo "Copying base files to shared volume"
   stop_and_copy_files
 
+  echo "Starting Consul primary cluster"
   start_consul primary
 
   if is_set $REQUIRE_SECONDARY; then