diff --git a/gbm-cli/cmd/release/status.go b/gbm-cli/cmd/release/status.go
index 2f1ef95..a695b7d 100644
--- a/gbm-cli/cmd/release/status.go
+++ b/gbm-cli/cmd/release/status.go
@@ -2,6 +2,7 @@ package release
 
 import (
 	"fmt"
+	"reflect"
 	"time"
 
 	"github.com/fatih/color"
@@ -39,7 +40,7 @@ var StatusCmd = &cobra.Command{
 			// Check to see if the release has been published
 			rel, _ := release.GetGbmRelease(version)
 
-			if (rel != gh.Release{}) {
+			if (!reflect.DeepEqual(rel, gh.Release{})) {
 				console.Print(heading, "\n🎉 Release %s has been published!\n %s\n", version, rel.Url)
 			}
 
diff --git a/gbm-cli/cmd/root.go b/gbm-cli/cmd/root.go
index 97b7b9c..e921336 100644
--- a/gbm-cli/cmd/root.go
+++ b/gbm-cli/cmd/root.go
@@ -4,8 +4,8 @@ import (
 	"github.com/spf13/cobra"
 	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/cmd/release"
 	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/cmd/render"
+	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/cmd/utils"
 	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/pkg/console"
-	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/pkg/gh"
 )
 
 const Version = "v1.5.0"
@@ -20,20 +20,13 @@ var rootCmd = &cobra.Command{
 func Execute() {
 	err := rootCmd.Execute()
 	console.ExitIfError(err)
-
 }
 
 func init() {
 	// Add the render command
 	rootCmd.AddCommand(render.RenderCmd)
 	rootCmd.AddCommand(release.ReleaseCmd)
-
-	// Check to see if the user is running the latest version
-	// of the CLI. If not, let them know.
-	latestRelease, err := gh.GetLatestRelease("release-toolkit-gutenberg-mobile")
-	console.ExitIfError(err)
-
-	if latestRelease.TagName != Version {
-		console.Warn("You are running an older version of the CLI. Please update to %s", latestRelease.TagName)
+	if !utils.CheckIfTempRun() {
+		utils.CheckExeVersion(Version)
 	}
 }
diff --git a/gbm-cli/cmd/utils/utils.go b/gbm-cli/cmd/utils/utils.go
index 0db3cd5..ec3d0e2 100644
--- a/gbm-cli/cmd/utils/utils.go
+++ b/gbm-cli/cmd/utils/utils.go
@@ -2,9 +2,15 @@ package utils
 
 import (
 	"fmt"
+	"net/http"
 	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
 
+	"github.com/inconshreveable/go-update"
 	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/pkg/console"
+	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/pkg/gh"
 	"github.com/wordpress-mobile/release-toolkit-gutenberg-mobile/gbm-cli/pkg/semver"
 )
 
@@ -35,3 +41,73 @@ func Exit(code int, deferred ...func()) {
 		return code
 	}())
 }
+
+// Checks if running from a temp directory (go build)
+// Useful for checking if running via `go run main.go`
+// We ignore errors since this only relevant to local development
+func CheckIfTempRun() bool {
+	ex, _ := os.Executable()
+	dir := filepath.Dir(ex)
+	return strings.Contains(dir, "go-build")
+}
+
+// Updates the currently running executable.
+func UpdateExe(url string) error {
+	resp, err := http.Get(url)
+	if err != nil {
+		return err
+	}
+	defer resp.Body.Close()
+	if err := update.Apply(resp.Body, update.Options{}); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+// Gets the download url for the gbm-cli executable
+func exeDownloadUrl(release gh.Release) string {
+	for _, asset := range release.Assets {
+		if strings.Contains(asset.Name, "gbm-cli") {
+			return asset.DownloadUrl
+		}
+	}
+	return ""
+}
+
+// Checks if the currently running executable is the latest version
+// If not, prompts the user to update.
+// If update is confirmed, the executable is updated and the process is restarted
+func CheckExeVersion(version string) {
+	latestRelease, err := gh.GetLatestRelease("release-toolkit-gutenberg-mobile")
+	console.ExitIfError(err)
+
+	if latestRelease.TagName != version {
+		if console.Confirm("You are running an older version of the CLI. Would you like to update?") {
+
+			if url := exeDownloadUrl(latestRelease); url != "" {
+				if err := UpdateExe(url); err != nil {
+					console.ExitError("Could not update the CLI: %v", err)
+				} else {
+					console.Info("CLI updated successfully")
+					reStart()
+				}
+			} else {
+				console.ExitError("Could not find download url for latest release")
+			}
+		}
+	}
+}
+
+// Restarts the process
+func reStart() {
+	args := os.Args
+	cmd := exec.Command(args[0], args[1:]...)
+	cmd.Stdout = os.Stdout
+	cmd.Stderr = os.Stderr
+	cmd.Stdin = os.Stdin
+	if err := cmd.Run(); err != nil {
+		os.Exit(1)
+	}
+	os.Exit(0)
+}
diff --git a/gbm-cli/go.mod b/gbm-cli/go.mod
index 65eecb9..07f1d32 100644
--- a/gbm-cli/go.mod
+++ b/gbm-cli/go.mod
@@ -7,6 +7,7 @@ toolchain go1.21.2
 require (
 	github.com/davecgh/go-spew v1.1.1
 	github.com/fatih/color v1.15.0
+	github.com/inconshreveable/go-update v0.0.0-20160112193335-8152e7eb6ccf
 	github.com/kylelemons/godebug v1.1.0
 	github.com/mikefarah/yq/v4 v4.35.2
 	github.com/spf13/cobra v1.7.0
diff --git a/gbm-cli/go.sum b/gbm-cli/go.sum
index c66bef9..f0b19e7 100644
--- a/gbm-cli/go.sum
+++ b/gbm-cli/go.sum
@@ -35,6 +35,8 @@ github.com/henvic/httpretty v0.1.2 h1:EQo556sO0xeXAjP10eB+BZARMuvkdGqtfeS4Ntjvki
 github.com/henvic/httpretty v0.1.2/go.mod h1:ViEsly7wgdugYtymX54pYp6Vv2wqZmNHayJ6q8tlKCc=
 github.com/hexops/gotextdiff v1.0.3 h1:gitA9+qJrrTCsiCl7+kh75nPqQt1cx4ZkudSTLoUqJM=
 github.com/hexops/gotextdiff v1.0.3/go.mod h1:pSWU5MAI3yDq+fZBTazCSJysOMbxWL1BSow5/V2vxeg=
+github.com/inconshreveable/go-update v0.0.0-20160112193335-8152e7eb6ccf h1:WfD7VjIE6z8dIvMsI4/s+1qr5EL+zoIGev1BQj1eoJ8=
+github.com/inconshreveable/go-update v0.0.0-20160112193335-8152e7eb6ccf/go.mod h1:hyb9oH7vZsitZCiBt0ZvifOrB+qc8PS5IiilCIb87rg=
 github.com/inconshreveable/mousetrap v1.1.0 h1:wN+x4NVGpMsO7ErUn/mUI3vEoE6Jt13X2s0bqwp9tc8=
 github.com/inconshreveable/mousetrap v1.1.0/go.mod h1:vpF70FUmC8bwa3OWnCshd2FqLfsEA9PFc4w1p2J65bw=
 github.com/jinzhu/copier v0.4.0 h1:w3ciUoD19shMCRargcpm0cm91ytaBhDvuRpz1ODO/U8=
diff --git a/gbm-cli/pkg/gh/gh.go b/gbm-cli/pkg/gh/gh.go
index 31f80eb..0701776 100644
--- a/gbm-cli/pkg/gh/gh.go
+++ b/gbm-cli/pkg/gh/gh.go
@@ -102,6 +102,15 @@ type Release struct {
 	Prerelease  bool
 	Target      string `json:"target_commitish"`
 	PublishedAt string `json:"published_at"`
+	Checksum    string
+	Assets      []ReleaseAsset
+}
+
+type ReleaseAsset struct {
+	Name        string
+	ContentType string `json:"content_type"`
+	Size        int
+	DownloadUrl string `json:"browser_download_url"`
 }
 
 type Commit struct {