diff --git a/commands/cloud_deploy.go b/commands/cloud_deploy.go
index 1693827..753a76b 100644
--- a/commands/cloud_deploy.go
+++ b/commands/cloud_deploy.go
@@ -75,6 +75,7 @@ func (d *KoolDeploy) Execute(args []string) (err error) {
 	var (
 		filename      string
 		deployCreated *api.DeployCreateResponse
+		isVerbose     = d.env.IsTrue("KOOL_VERBOSE")
 
 		deployer = cloud.NewDeployer()
 	)
@@ -97,10 +98,30 @@ func (d *KoolDeploy) Execute(args []string) (err error) {
 	}
 	s.Stop()
 
+	var chPingDone = make(chan bool)
+	go func() {
+		for {
+			select {
+			case <-chPingDone:
+				if isVerbose {
+					fmt.Println(" - ending deploy ping routine")
+				}
+				return
+			case <-time.After(30 * time.Second):
+				if isVerbose {
+					fmt.Println(" - going to ping API while local build runs")
+				}
+				if _, err = deployer.PingDeploy(deployCreated); err != nil {
+					d.Shell().Error(err)
+				}
+			}
+		}
+	}()
+
 	d.Shell().Info("Building images...")
 	for svcName, svc := range d.cloudConfig.Cloud.Services {
 		if svc.Build != nil {
-			d.Shell().Info("  > Build deploy image for service: ", svcName)
+			d.Shell().Info("  > Build deploy image for service '", svcName, "'")
 
 			if err = cloud.BuildPushImageForDeploy(svcName, svc, deployCreated); err != nil {
 				if reportErr := deployer.BuildError(deployCreated, err); reportErr != nil {
@@ -110,10 +131,13 @@ func (d *KoolDeploy) Execute(args []string) (err error) {
 				return
 			}
 
-			d.Shell().Info("  > Image for service: ", svcName, " built & pushed successfully.")
+			d.Shell().Info("  > Image for service '", svcName, "' built & pushed successfully.")
 		}
 	}
 
+	// ends ping
+	chPingDone <- true
+
 	if deployCreated.LogsUrl != "" {
 		d.Shell().Info(strings.Repeat("-", 40))
 		d.Shell().Info("Logs available at: ", deployCreated.LogsUrl)
diff --git a/commands/root.go b/commands/root.go
index 3c078e1..7cbd52a 100644
--- a/commands/root.go
+++ b/commands/root.go
@@ -6,6 +6,7 @@ import (
 	"kool-dev/kool/core/environment"
 	"kool-dev/kool/core/parser"
 	"kool-dev/kool/core/shell"
+	"kool-dev/kool/services/cloud/api"
 	"os"
 	"path"
 	"path/filepath"
@@ -52,6 +53,9 @@ var originalWorkingDir = ""
 
 func init() {
 	AddCommands(rootCmd)
+
+	// pass in the version
+	api.SetCliVersion(version)
 }
 
 // NewRootCmd creates the root command
diff --git a/services/cloud/api/api.go b/services/cloud/api/api.go
index e500410..9ffeb90 100644
--- a/services/cloud/api/api.go
+++ b/services/cloud/api/api.go
@@ -2,6 +2,8 @@ package api
 
 var (
 	apiBaseURL string = "https://kool.dev/api"
+
+	cliVersion string
 )
 
 // SetBaseURL defines the target Kool API URL to be used
@@ -9,3 +11,8 @@ var (
 func SetBaseURL(url string) {
 	apiBaseURL = url
 }
+
+// SetCliVersion injects version to this package
+func SetCliVersion(v string) {
+	cliVersion = v
+}
diff --git a/services/cloud/api/deploy_ping.go b/services/cloud/api/deploy_ping.go
new file mode 100644
index 0000000..d99449c
--- /dev/null
+++ b/services/cloud/api/deploy_ping.go
@@ -0,0 +1,34 @@
+package api
+
+import "fmt"
+
+// DeployPingResponse holds data returned from the deploy endpoint
+type DeployPingResponse struct {
+	ID     int    `json:"id"`
+	Status string `json:"status"`
+}
+
+// DeployPing consumes the API endpoint to create a new deployment
+type DeployPing struct {
+	Endpoint
+}
+
+// NewDeployPing creates a new DeployStart instance
+func NewDeployPing(created *DeployCreateResponse) (c *DeployPing) {
+	c = &DeployPing{
+		Endpoint: NewDefaultEndpoint("POST"),
+	}
+
+	c.SetPath("deploy/ping")
+	c.Body().Set("id", fmt.Sprintf("%d", created.Deploy.ID))
+
+	return
+}
+
+// Run calls deploy/ping in the Kool Dev API
+func (c *DeployPing) Run() (resp *DeployPingResponse, err error) {
+	resp = &DeployPingResponse{}
+	c.SetResponseReceiver(resp)
+	err = c.DoCall()
+	return
+}
diff --git a/services/cloud/api/endpoint.go b/services/cloud/api/endpoint.go
index 75601d1..bf73c65 100644
--- a/services/cloud/api/endpoint.go
+++ b/services/cloud/api/endpoint.go
@@ -189,6 +189,8 @@ func (e *DefaultEndpoint) DoCall() (err error) {
 		return
 	}
 
+	request.Header.Add("x-kool-cli-version", cliVersion)
+
 	if e.contentType != "" {
 		request.Header.Add("Content-type", e.contentType)
 	}
diff --git a/services/cloud/deployer.go b/services/cloud/deployer.go
index 28c2d14..367e37e 100644
--- a/services/cloud/deployer.go
+++ b/services/cloud/deployer.go
@@ -46,6 +46,13 @@ func (d *Deployer) StartDeploy(created *api.DeployCreateResponse) (started *api.
 	return
 }
 
+func (d *Deployer) PingDeploy(created *api.DeployCreateResponse) (pinged *api.DeployPingResponse, err error) {
+	var ping = api.NewDeployPing(created)
+
+	pinged, err = ping.Run()
+	return
+}
+
 func (d *Deployer) BuildError(created *api.DeployCreateResponse, gotErr error) (err error) {
 	var buildErr = api.NewDeployError(created, gotErr)