diff --git a/Makefile b/Makefile
index b369bf7a545..a8fa273b29c 100644
--- a/Makefile
+++ b/Makefile
@@ -8,8 +8,9 @@ BUILD_CHANNEL ?= local
 PATH_WITH_TOOLS="`pwd`/$(TOOL_BIN):`pwd`/node_modules/.bin:${PATH}"
 
 GIT_REVISION = $(shell git rev-parse HEAD | tr -d '\n')
-TAG_VERSION?=$(shell git tag --points-at | sort -Vr | head -n1)
-LDFLAGS = -ldflags "-s -w -extld="$(shell pwd)/etc/ld_wrapper.sh" -X 'go.viam.com/rdk/config.Version=${TAG_VERSION}' -X 'go.viam.com/rdk/config.GitRevision=${GIT_REVISION}'"
+TAG_VERSION?=$(shell git tag --points-at | sort -Vr | head -n1 | grep . || echo "(dev)")
+DATE_COMPILED?=$(shell date +'%Y-%m-%d')
+LDFLAGS = -ldflags "-s -w -extld="$(shell pwd)/etc/ld_wrapper.sh" -X 'go.viam.com/rdk/config.Version=${TAG_VERSION}' -X 'go.viam.com/rdk/config.GitRevision=${GIT_REVISION}' -X 'go.viam.com/rdk/config.DateCompiled=${DATE_COMPILED}'"
 ifeq ($(shell command -v dpkg >/dev/null && dpkg --print-architecture),armhf)
 GOFLAGS += -tags=no_tflite
 endif
diff --git a/cli/app.go b/cli/app.go
index 767dfd19235..b35b5f5cbdc 100644
--- a/cli/app.go
+++ b/cli/app.go
@@ -19,6 +19,9 @@ const (
 	aliasRobotFlag   = "robot"
 	partFlag         = "part"
 
+	// TODO: RSDK-6683.
+	quietFlag = "quiet"
+
 	logsFlagErrors = "errors"
 	logsFlagTail   = "tail"
 
@@ -109,6 +112,12 @@ var app = &cli.App{
 			Aliases: []string{"vvv"},
 			Usage:   "enable debug logging",
 		},
+		&cli.BoolFlag{
+			Name:    quietFlag,
+			Value:   false,
+			Aliases: []string{"q"},
+			Usage:   "suppress warnings",
+		},
 	},
 	Commands: []*cli.Command{
 		{
@@ -124,6 +133,7 @@ var app = &cli.App{
 				},
 			},
 			Action: LoginAction,
+			After:  CheckUpdateAction,
 			Subcommands: []*cli.Command{
 				{
 					Name:   "print-access-token",
diff --git a/cli/client.go b/cli/client.go
index ee2f0e1d39f..5b45e7f0037 100644
--- a/cli/client.go
+++ b/cli/client.go
@@ -3,9 +3,11 @@ package cli
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
 	"io"
 	"net"
+	"net/http"
 	"net/url"
 	"os"
 	"os/exec"
@@ -13,6 +15,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/Masterminds/semver/v3"
 	"github.com/fullstorydev/grpcurl"
 	"github.com/google/uuid"
 	"github.com/jhump/protoreflect/grpcreflect"
@@ -40,6 +43,10 @@ import (
 	"go.viam.com/rdk/services/shell"
 )
 
+const (
+	rdkReleaseURL = "https://api.github.com/repos/viamrobotics/rdk/releases/latest"
+)
+
 // viamClient wraps a cli.Context and provides all the CLI command functionality
 // needed to talk to the app and data services but not directly to robot parts.
 type viamClient struct {
@@ -380,6 +387,129 @@ func RobotsPartShellAction(c *cli.Context) error {
 	)
 }
 
+// checkUpdateResponse holds the values used to hold release information.
+type getLatestReleaseResponse struct {
+	Name       string `json:"name"`
+	TagName    string `json:"tag_name"`
+	TarballURL string `json:"tarball_url"`
+}
+
+func getLatestReleaseVersion() (string, error) {
+	ctx, cancel := context.WithTimeout(context.Background(), time.Second)
+	defer cancel()
+
+	resp := getLatestReleaseResponse{}
+
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, rdkReleaseURL, nil)
+	if err != nil {
+		return "", err
+	}
+
+	client := http.DefaultClient
+	res, err := client.Do(req)
+	if err != nil {
+		return "", err
+	}
+
+	err = json.NewDecoder(res.Body).Decode(&resp)
+	if err != nil {
+		return "", err
+	}
+
+	defer utils.UncheckedError(res.Body.Close())
+	return resp.TagName, err
+}
+
+// CheckUpdateAction is the corresponding Action for 'check-update'.
+func CheckUpdateAction(c *cli.Context) error {
+	if c.Bool(quietFlag) {
+		return nil
+	}
+
+	dateCompiledRaw := rconfig.DateCompiled
+
+	// `go build` will not set the compilation flags needed for this check
+	if dateCompiledRaw == "" {
+		return nil
+	}
+
+	dateCompiled, err := time.Parse("2006-01-02", dateCompiledRaw)
+	if err != nil {
+		warningf(c.App.ErrWriter, "CLI Update Check: failed to parse compilation date: %w", err)
+		return nil
+	}
+
+	// install is less than six weeks old
+	if time.Since(dateCompiled) < time.Hour*24*7*6 {
+		return nil
+	}
+
+	conf, err := configFromCache()
+	if err != nil {
+		if !os.IsNotExist(err) {
+			utils.UncheckedError(err)
+			return nil
+		}
+		conf = &config{}
+	}
+
+	var lastCheck time.Time
+	if conf.LastUpdateCheck == "" {
+		conf.LastUpdateCheck = time.Now().Format("2006-01-02")
+	} else {
+		lastCheck, err = time.Parse("2006-01-02", conf.LastUpdateCheck)
+		if err != nil {
+			warningf(c.App.ErrWriter, "CLI Update Check: failed to parse date of last check: %w", err)
+			return nil
+		}
+	}
+
+	// The latest version info is cached to limit api calls to once every three days
+	if time.Since(lastCheck) < time.Hour*24*3 && conf.LatestVersion != "" {
+		warningf(c.App.ErrWriter, "CLI Update Check: Your CLI is more than 6 weeks old. "+
+			"Consider updating to version: %s", conf.LatestVersion)
+		return nil
+	}
+
+	latestRelease, err := getLatestReleaseVersion()
+	if err != nil {
+		warningf(c.App.ErrWriter, "CLI Update Check: failed to get latest release information: %w", err)
+		return nil
+	}
+
+	latestVersion, err := semver.NewVersion(latestRelease)
+	if err != nil {
+		warningf(c.App.ErrWriter, "CLI Update Check: failed to parse latest version: %w", err)
+		return nil
+	}
+
+	conf.LatestVersion = latestVersion.String()
+
+	err = storeConfigToCache(conf)
+	if err != nil {
+		utils.UncheckedError(err)
+	}
+
+	appVersion := rconfig.Version
+	if appVersion == "(dev)" {
+		warningf(c.App.ErrWriter, "CLI Update Check: Your CLI is more than 6 weeks old. "+
+			"Consider updating to version: %s", latestVersion.Original())
+		return nil
+	}
+
+	localVersion, err := semver.NewVersion(appVersion)
+	if err != nil {
+		warningf(c.App.ErrWriter, "CLI Update Check: failed to parse compiled version: %w", err)
+		return nil
+	}
+
+	if localVersion.LessThan(latestVersion) {
+		warningf(c.App.ErrWriter, "CLI Update Check: Your CLI is out of date. Consider updating to version %s", latestVersion.Original())
+	}
+
+	return nil
+}
+
 // VersionAction is the corresponding Action for 'version'.
 func VersionAction(c *cli.Context) error {
 	info, ok := debug.ReadBuildInfo()
@@ -408,10 +538,8 @@ func VersionAction(c *cli.Context) error {
 	if dep, ok := deps["go.viam.com/api"]; ok {
 		apiVersion = dep.Version
 	}
+
 	appVersion := rconfig.Version
-	if appVersion == "" {
-		appVersion = "(dev)"
-	}
 	printf(c.App.Writer, "Version %s Git=%s API=%s", appVersion, version, apiVersion)
 	return nil
 }
diff --git a/cli/config.go b/cli/config.go
index c5222876831..592b2b48bb5 100644
--- a/cli/config.go
+++ b/cli/config.go
@@ -51,8 +51,10 @@ func storeConfigToCache(cfg *config) error {
 }
 
 type config struct {
-	BaseURL string     `json:"base_url"`
-	Auth    authMethod `json:"auth"`
+	BaseURL         string     `json:"base_url"`
+	Auth            authMethod `json:"auth"`
+	LastUpdateCheck string     `json:"last_update_check"`
+	LatestVersion   string     `json:"latest_version"`
 }
 
 func (conf *config) tryUnmarshallWithToken(configBytes []byte) error {
diff --git a/cli/print.go b/cli/print.go
index e4dcfd119cb..10bf467236f 100644
--- a/cli/print.go
+++ b/cli/print.go
@@ -38,12 +38,6 @@ func infof(w io.Writer, format string, a ...interface{}) {
 }
 
 // warningf prints a message prefixed with a bold yellow "Warning: ".
-//
-// NOTE(benjirewis): we disable the unparam linter here. Our usages of warningf
-// do not currently make use of the variadic `a` parameter but may in the
-// future. unparam will complain until it does.
-//
-//nolint:unparam
 func warningf(w io.Writer, format string, a ...interface{}) {
 	if _, err := color.New(color.Bold, color.FgYellow).Fprint(w, "Warning: "); err != nil {
 		log.Fatal(err)
diff --git a/config/reader.go b/config/reader.go
index e33fbd8c770..36bccce3924 100644
--- a/config/reader.go
+++ b/config/reader.go
@@ -26,8 +26,9 @@ import (
 
 // RDK versioning variables which are replaced by LD flags.
 var (
-	Version     = ""
-	GitRevision = ""
+	Version      = ""
+	GitRevision  = ""
+	DateCompiled = ""
 )
 
 func getAgentInfo() (*apppb.AgentInfo, error) {
diff --git a/go.mod b/go.mod
index 3f96fa14b33..8193d8c9367 100644
--- a/go.mod
+++ b/go.mod
@@ -5,6 +5,7 @@ go 1.19
 require (
 	github.com/AlekSi/gocov-xml v1.0.0
 	github.com/CPRT/roboclaw v0.0.0-20190825181223-76871438befc
+	github.com/Masterminds/semver/v3 v3.2.1
 	github.com/Masterminds/sprig v2.22.0+incompatible
 	github.com/NYTimes/gziphandler v1.1.1
 	github.com/a8m/envsubst v1.4.2
diff --git a/go.sum b/go.sum
index 5e21c720eae..3729a648ff9 100644
--- a/go.sum
+++ b/go.sum
@@ -91,6 +91,8 @@ github.com/Masterminds/goutils v1.1.1/go.mod h1:8cTjp+g8YejhMuvIA5y2vz3BpJxksy86
 github.com/Masterminds/semver v1.4.2/go.mod h1:MB6lktGJrhw8PrUyiEoblNEGEQ+RzHPF078ddwwvV3Y=
 github.com/Masterminds/semver v1.5.0 h1:H65muMkzWKEuNDnfl9d70GUjFniHKHRbFPGBuZ3QEww=
 github.com/Masterminds/semver v1.5.0/go.mod h1:MB6lktGJrhw8PrUyiEoblNEGEQ+RzHPF078ddwwvV3Y=
+github.com/Masterminds/semver/v3 v3.2.1 h1:RN9w6+7QoMeJVGyfmbcgs28Br8cvmnucEXnY0rYXWg0=
+github.com/Masterminds/semver/v3 v3.2.1/go.mod h1:qvl/7zhW3nngYb5+80sSMF+FG2BjYrf8m9wsX0PNOMQ=
 github.com/Masterminds/sprig v2.15.0+incompatible/go.mod h1:y6hNFY5UBTIWBxnzTeuNhlNS5hqE0NB0E6fgfo2Br3o=
 github.com/Masterminds/sprig v2.22.0+incompatible h1:z4yfnGrZ7netVz+0EDJ0Wi+5VZCSYp4Z0m2dk6cEM60=
 github.com/Masterminds/sprig v2.22.0+incompatible/go.mod h1:y6hNFY5UBTIWBxnzTeuNhlNS5hqE0NB0E6fgfo2Br3o=