diff --git a/cmd/humanlog/main.go b/cmd/humanlog/main.go
index c3ac341..5253cf5 100644
--- a/cmd/humanlog/main.go
+++ b/cmd/humanlog/main.go
@@ -11,7 +11,6 @@ import (
 
 	"github.com/aybabtme/rgbterm"
 	"github.com/blang/semver"
-	"github.com/fatih/color"
 	types "github.com/humanlogio/api/go/types/v1"
 	"github.com/humanlogio/humanlog"
 	"github.com/humanlogio/humanlog/internal/pkg/config"
@@ -165,11 +164,12 @@ func newApp() *cli.App {
 	app.Usage = "reads structured logs from stdin, makes them pretty on stdout!"
 
 	var (
-		ctx       context.Context
-		cancel    context.CancelFunc
-		cfg       *config.Config
-		statefile *state.State
-		updateRes <-chan *checkForUpdateRes
+		ctx              context.Context
+		cancel           context.CancelFunc
+		cfg              *config.Config
+		statefile        *state.State
+		promptedToUpdate *semver.Version
+		updateRes        <-chan *checkForUpdateRes
 	)
 
 	app.Before = func(c *cli.Context) error {
@@ -205,6 +205,11 @@ func newApp() *cli.App {
 			return fmt.Errorf("reading default config file: %v", err)
 		}
 
+		if statefile.LatestKnownVersion != nil && statefile.LatestKnownVersion.GT(semverVersion) {
+			promptToUpdate(semverVersion, *statefile.LatestKnownVersion)
+			promptedToUpdate = statefile.LatestKnownVersion
+		}
+
 		if shouldCheckForUpdate(c, cfg, statefile) {
 			req := &checkForUpdateReq{
 				arch:    runtime.GOARCH,
@@ -222,14 +227,11 @@ func newApp() *cli.App {
 			if !ok {
 				return nil
 			}
-
-			if res.hasUpdate {
-				log.Print(
-					color.YellowString("Update available %s -> %s.", semverVersion, res.sem),
-				)
-				log.Print(
-					color.YellowString("Run %s to upgrade.", color.New(color.Bold).Sprint("humanlog version update")),
-				)
+			if res.hasUpdate && promptedToUpdate == nil && promptedToUpdate.LT(res.sem) {
+				alreadyPromptedForSameUpdate := promptedToUpdate != nil && promptedToUpdate.GTE(res.sem)
+				if !alreadyPromptedForSameUpdate {
+					promptToUpdate(semverVersion, res.sem)
+				}
 			}
 		default:
 		}
diff --git a/cmd/humanlog/versions.go b/cmd/humanlog/versions.go
index 8b6c4e0..07eb7f6 100644
--- a/cmd/humanlog/versions.go
+++ b/cmd/humanlog/versions.go
@@ -58,7 +58,7 @@ func reqMeta(st *state.State) *types.ReqMeta {
 	return req
 }
 
-func updateFromResMeta(st *state.State, res *types.ResMeta, lastUpdateCheck *time.Time) error {
+func updateFromResMeta(st *state.State, res *types.ResMeta, latestKnownVersion *semver.Version, latestKnownVersionUpdatedAt *time.Time) error {
 	changed := false
 	if st.AccountID == nil || res.AccountId != *st.AccountID {
 		st.AccountID = &res.AccountId
@@ -68,8 +68,18 @@ func updateFromResMeta(st *state.State, res *types.ResMeta, lastUpdateCheck *tim
 		st.MachineID = &res.MachineId
 		changed = true
 	}
-	if st.LastUpdateCheckAt == nil && lastUpdateCheck != nil {
-		st.LastUpdateCheckAt = lastUpdateCheck
+	if st.LatestKnownVersion == nil && latestKnownVersion != nil {
+		st.LatestKnownVersion = latestKnownVersion
+		changed = true
+	} else if st.LatestKnownVersion != nil && latestKnownVersion != nil && !st.LatestKnownVersion.EQ(*latestKnownVersion) {
+		st.LatestKnownVersion = latestKnownVersion
+		changed = true
+	}
+	if st.LastestKnownVersionUpdatedAt == nil && latestKnownVersionUpdatedAt != nil {
+		st.LastestKnownVersionUpdatedAt = latestKnownVersionUpdatedAt
+		changed = true
+	} else if st.LastestKnownVersionUpdatedAt != nil && latestKnownVersionUpdatedAt != nil && !st.LastestKnownVersionUpdatedAt.Equal(*latestKnownVersionUpdatedAt) {
+		st.LastestKnownVersionUpdatedAt = latestKnownVersionUpdatedAt
 		changed = true
 	}
 	if !changed {
@@ -106,12 +116,7 @@ func versionCmd(
 					if err != nil {
 						return fmt.Errorf("invalid semver received: %w", err)
 					}
-					log.Print(
-						color.YellowString("Update available %s -> %s.", semverVersion, nextSV),
-					)
-					log.Print(
-						color.YellowString("Run %s to upgrade.", color.New(color.Bold).Sprint("humanlog version update")),
-					)
+					promptToUpdate(semverVersion, nextSV)
 					log.Printf("- url: %s", nextArtifact.Url)
 					log.Printf("- sha256: %s", nextArtifact.Sha256)
 					log.Printf("- sig: %s", nextArtifact.Signature)
@@ -173,14 +178,14 @@ func checkForUpdate(ctx context.Context, cfg *config.Config, state *state.State)
 	msg := res.Msg
 
 	lastCheckAt := time.Now()
-	if err := updateFromResMeta(state, msg.Meta, &lastCheckAt); err != nil {
-		log.Printf("failed to persist internal state: %v", err)
-	}
-
 	nextSV, err := msg.NextVersion.AsSemver()
 	if err != nil {
 		return nil, nil, false, err
 	}
+	if err := updateFromResMeta(state, msg.Meta, &nextSV, &lastCheckAt); err != nil {
+		log.Printf("failed to persist internal state: %v", err)
+	}
+
 	return msg.NextVersion, msg.NextArtifact, currentSV.LT(nextSV), nil
 }
 
@@ -207,3 +212,12 @@ func asyncCheckForUpdate(ctx context.Context, req *checkForUpdateReq, cfg *confi
 	}()
 	return out
 }
+
+func promptToUpdate(from, to semver.Version) {
+	log.Print(
+		color.YellowString("Update available %s -> %s.", from, to),
+	)
+	log.Print(
+		color.YellowString("Run `%s` to upgrade.", color.New(color.Bold).Sprint("humanlog version update")),
+	)
+}
diff --git a/internal/pkg/state/state.go b/internal/pkg/state/state.go
index 8dad345..653dbe6 100644
--- a/internal/pkg/state/state.go
+++ b/internal/pkg/state/state.go
@@ -7,6 +7,8 @@ import (
 	"os"
 	"path/filepath"
 	"time"
+
+	"github.com/blang/semver"
 )
 
 var DefaultState = State{
@@ -93,10 +95,11 @@ func WriteStateFile(path string, state *State) error {
 }
 
 type State struct {
-	Version           int        `json:"version"`
-	AccountID         *int64     `json:"account_id"`
-	MachineID         *int64     `json:"machine_id"`
-	LastUpdateCheckAt *time.Time `json:"last_update_check_at"`
+	Version                      int             `json:"version"`
+	AccountID                    *int64          `json:"account_id"`
+	MachineID                    *int64          `json:"machine_id"`
+	LatestKnownVersion           *semver.Version `json:"latest_known_version,omitempty"`
+	LastestKnownVersionUpdatedAt *time.Time      `json:"latest_known_version_updated_at"`
 
 	// unexported
 	path string