diff --git a/checkpoint.go b/checkpoint.go
new file mode 100644
index 000000000..ebe592b32
--- /dev/null
+++ b/checkpoint.go
@@ -0,0 +1,81 @@
+package main
+
+import (
+	"fmt"
+	"log"
+	"path/filepath"
+
+	"github.com/hashicorp/go-checkpoint"
+	"github.com/hashicorp/terraform/command"
+)
+
+func init() {
+	checkpointResult = make(chan *checkpoint.CheckResponse, 1)
+}
+
+var checkpointResult chan *checkpoint.CheckResponse
+
+// runCheckpoint runs a HashiCorp Checkpoint request. You can read about
+// Checkpoint here: https://github.com/hashicorp/go-checkpoint.
+func runCheckpoint(c *Config) {
+	// If the user doesn't want checkpoint at all, then return.
+	if c.DisableCheckpoint {
+		log.Printf("[INFO] Checkpoint disabled. Not running.")
+		checkpointResult <- nil
+		return
+	}
+
+	configDir, err := ConfigDir()
+	if err != nil {
+		log.Printf("[ERR] Checkpoint setup error: %s", err)
+		checkpointResult <- nil
+		return
+	}
+
+	version := Version
+	if VersionPrerelease != "" {
+		version += fmt.Sprintf(".%s", VersionPrerelease)
+	}
+
+	signaturePath := filepath.Join(configDir, "checkpoint_signature")
+	if c.DisableCheckpointSignature {
+		log.Printf("[INFO] Checkpoint signature disabled")
+		signaturePath = ""
+	}
+
+	resp, err := checkpoint.Check(&checkpoint.CheckParams{
+		Product:       "terraform",
+		Version:       version,
+		SignatureFile: signaturePath,
+		CacheFile:     filepath.Join(configDir, "checkpoint_cache"),
+	})
+	if err != nil {
+		log.Printf("[ERR] Checkpoint error: %s", err)
+		resp = nil
+	}
+
+	checkpointResult <- resp
+}
+
+// commandVersionCheck implements command.VersionCheckFunc and is used
+// as the version checker.
+func commandVersionCheck() (command.VersionCheckInfo, error) {
+	// Wait for the result to come through
+	info := <-checkpointResult
+	if info == nil {
+		var zero command.VersionCheckInfo
+		return zero, nil
+	}
+
+	// Build the alerts that we may have received about our version
+	alerts := make([]string, len(info.Alerts))
+	for i, a := range info.Alerts {
+		alerts[i] = a.Message
+	}
+
+	return command.VersionCheckInfo{
+		Outdated: info.Outdated,
+		Latest:   info.CurrentVersion,
+		Alerts:   alerts,
+	}, nil
+}
diff --git a/command/version.go b/command/version.go
index 17015e604..729f55aa7 100644
--- a/command/version.go
+++ b/command/version.go
@@ -12,6 +12,20 @@ type VersionCommand struct {
 	Revision          string
 	Version           string
 	VersionPrerelease string
+	CheckFunc         VersionCheckFunc
+}
+
+// VersionCheckFunc is the callback called by the Version command to
+// check if there is a new version of Terraform.
+type VersionCheckFunc func() (VersionCheckInfo, error)
+
+// VersionCheckInfo is the return value for the VersionCheckFunc callback
+// and tells the Version command information about the latest version
+// of Terraform.
+type VersionCheckInfo struct {
+	Outdated bool
+	Latest   string
+	Alerts   []string
 }
 
 func (c *VersionCommand) Help() string {
@@ -20,7 +34,6 @@ func (c *VersionCommand) Help() string {
 
 func (c *VersionCommand) Run(args []string) int {
 	var versionString bytes.Buffer
-
 	args = c.Meta.process(args, false)
 
 	fmt.Fprintf(&versionString, "Terraform v%s", c.Version)
@@ -33,6 +46,27 @@ func (c *VersionCommand) Run(args []string) int {
 	}
 
 	c.Ui.Output(versionString.String())
+
+	// If we have a version check function, then let's check for
+	// the latest version as well.
+	if c.CheckFunc != nil {
+		// Separate the prior output with a newline
+		c.Ui.Output("")
+
+		// Check the latest version
+		info, err := c.CheckFunc()
+		if err != nil {
+			c.Ui.Error(fmt.Sprintf(
+				"Error checking latest version: %s", err))
+		}
+		if info.Outdated {
+			c.Ui.Output(fmt.Sprintf(
+				"Your version of Terraform is out of date! The latest version\n"+
+					"is %s. You can update by downloading from www.terraform.io",
+				info.Latest))
+		}
+	}
+
 	return 0
 }
 
diff --git a/commands.go b/commands.go
index b58011f1f..7c8a06eb2 100644
--- a/commands.go
+++ b/commands.go
@@ -96,6 +96,7 @@ func init() {
 				Revision:          GitCommit,
 				Version:           Version,
 				VersionPrerelease: VersionPrerelease,
+				CheckFunc:         commandVersionCheck,
 			}, nil
 		},
 	}
diff --git a/config.go b/config.go
index 7260f05a2..583d7ddb2 100644
--- a/config.go
+++ b/config.go
@@ -22,6 +22,9 @@ import (
 type Config struct {
 	Providers    map[string]string
 	Provisioners map[string]string
+
+	DisableCheckpoint          bool `hcl:"disable_checkpoint"`
+	DisableCheckpointSignature bool `hcl:"disable_checkpoint_signature"`
 }
 
 // BuiltinConfig is the built-in defaults for the configuration. These
diff --git a/main.go b/main.go
index 95eaab560..46f143ba5 100644
--- a/main.go
+++ b/main.go
@@ -92,6 +92,9 @@ func wrappedMain() int {
 		return 1
 	}
 
+	// Run checkpoint
+	go runCheckpoint(&config)
+
 	// Make sure we clean up any managed plugins at the end of this
 	defer plugin.CleanupClients()