diff --git a/cmd/server/main-server.go b/cmd/server/main-server.go
index b52d97491c..30540e351f 100644
--- a/cmd/server/main-server.go
+++ b/cmd/server/main-server.go
@@ -465,6 +465,10 @@ func main() {
 		return
 	}
 
+	err = shellutil.FixupWaveZshHistory()
+	if err != nil {
+		log.Printf("error fixing up wave zsh history: %v\n", err)
+	}
 	createMainWshClient()
 	sigutil.InstallShutdownSignalHandlers(doShutdown)
 	sigutil.InstallSIGUSR1Handler()
diff --git a/go.mod b/go.mod
index ef1927874f..6711ded66a 100644
--- a/go.mod
+++ b/go.mod
@@ -81,6 +81,7 @@ require (
 	github.com/lufia/plan9stats v0.0.0-20211012122336-39d0f177ccd0 // indirect
 	github.com/mailru/easyjson v0.7.7 // indirect
 	github.com/mattn/go-isatty v0.0.20 // indirect
+	github.com/outrigdev/goid v0.3.0 // indirect
 	github.com/power-devops/perfstat v0.0.0-20240221224432-82ca36839d55 // indirect
 	github.com/rivo/uniseg v0.4.7 // indirect
 	github.com/sirupsen/logrus v1.9.3 // indirect
diff --git a/go.sum b/go.sum
index ee73e96e87..ea416cd09a 100644
--- a/go.sum
+++ b/go.sum
@@ -146,6 +146,8 @@ github.com/mattn/go-sqlite3 v1.14.32 h1:JD12Ag3oLy1zQA+BNn74xRgaBbdhbNIDYvQUEuuE
 github.com/mattn/go-sqlite3 v1.14.32/go.mod h1:Uh1q+B4BYcTPb+yiD3kU8Ct7aC0hY9fxUwlHK0RXw+Y=
 github.com/mitchellh/mapstructure v1.5.0 h1:jeMsZIYE/09sWLaz43PL7Gy6RuMjD2eJVyuac5Z2hdY=
 github.com/mitchellh/mapstructure v1.5.0/go.mod h1:bFUtVrKA4DC2yAKiSyO/QUcy7e+RRV2QTWOzhPopBRo=
+github.com/outrigdev/goid v0.3.0 h1:t/otQD3EXc45cLtQVPUnNgEyRaTQA4cPeu3qVcrsIws=
+github.com/outrigdev/goid v0.3.0/go.mod h1:hEH7f27ypN/GHWt/7gvkRoFYR0LZizfUBIAbak4neVE=
 github.com/photostorm/pty v1.1.19-0.20230903182454-31354506054b h1:cLGKfKb1uk0hxI0Q8L83UAJPpeJ+gSpn3cCU/tjd3eg=
 github.com/photostorm/pty v1.1.19-0.20230903182454-31354506054b/go.mod h1:KO+FcPtyLAiRC0hJwreJVvfwc7vnNz77UxBTIGHdPVk=
 github.com/planetscale/vtprotobuf v0.6.1-0.20240319094008-0393e58bdf10 h1:GFCKgmp0tecUJ0sJuv4pzYCqS9+RGSn52M3FUwPs+uo=
diff --git a/pkg/telemetry/telemetry.go b/pkg/telemetry/telemetry.go
index 3a208055b9..24c7541b54 100644
--- a/pkg/telemetry/telemetry.go
+++ b/pkg/telemetry/telemetry.go
@@ -254,10 +254,13 @@ func RecordTEvent(ctx context.Context, tevent *telemetrydata.TEvent) error {
 }
 
 func CleanOldTEvents(ctx context.Context) error {
+	daysToKeep := 7
+	if !IsTelemetryEnabled() {
+		daysToKeep = 1
+	}
+	olderThan := time.Now().AddDate(0, 0, -daysToKeep).UnixMilli()
 	return wstore.WithTx(ctx, func(tx *wstore.TxWrap) error {
-		// delete events older than 28 days
 		query := `DELETE FROM db_tevent WHERE ts < ?`
-		olderThan := time.Now().AddDate(0, 0, -28).UnixMilli()
 		tx.Exec(query, olderThan)
 		return nil
 	})
diff --git a/pkg/util/envutil/envutil.go b/pkg/util/envutil/envutil.go
index c2505e7c47..dff40c1842 100644
--- a/pkg/util/envutil/envutil.go
+++ b/pkg/util/envutil/envutil.go
@@ -67,3 +67,27 @@ func RmEnv(envStr string, key string) string {
 	delete(envMap, key)
 	return MapToEnv(envMap)
 }
+
+func SliceToEnv(env []string) string {
+	var sb strings.Builder
+	for _, envVar := range env {
+		if len(envVar) == 0 {
+			continue
+		}
+		sb.WriteString(envVar)
+		sb.WriteByte('\x00')
+	}
+	return sb.String()
+}
+
+func EnvToSlice(envStr string) []string {
+	envLines := strings.Split(envStr, "\x00")
+	result := make([]string, 0, len(envLines))
+	for _, line := range envLines {
+		if len(line) == 0 {
+			continue
+		}
+		result = append(result, line)
+	}
+	return result
+}
diff --git a/pkg/util/shellutil/shellintegration/zsh_zshrc.sh b/pkg/util/shellutil/shellintegration/zsh_zshrc.sh
index f24abee181..0c0271a29d 100644
--- a/pkg/util/shellutil/shellintegration/zsh_zshrc.sh
+++ b/pkg/util/shellutil/shellintegration/zsh_zshrc.sh
@@ -18,6 +18,11 @@ if [[ -n ${_comps+x} ]]; then
   source <(wsh completion zsh)
 fi
 
+# fix history (macos)
+if [[ "$HISTFILE" == "$WAVETERM_ZDOTDIR/.zsh_history" ]]; then
+  HISTFILE="$HOME/.zsh_history"
+fi
+
 typeset -g _WAVETERM_SI_FIRSTPRECMD=1
 
 # shell integration
diff --git a/pkg/util/shellutil/shellutil.go b/pkg/util/shellutil/shellutil.go
index dd9fe697a1..a6268bf5dd 100644
--- a/pkg/util/shellutil/shellutil.go
+++ b/pkg/util/shellutil/shellutil.go
@@ -18,6 +18,7 @@ import (
 	"sync"
 	"time"
 
+	"github.com/wavetermdev/waveterm/pkg/util/envutil"
 	"github.com/wavetermdev/waveterm/pkg/util/utilfn"
 	"github.com/wavetermdev/waveterm/pkg/wavebase"
 	"github.com/wavetermdev/waveterm/pkg/waveobj"
@@ -47,6 +48,8 @@ var (
 
 	//go:embed shellintegration/pwsh_wavepwsh.sh
 	PwshStartup_wavepwsh string
+
+	ZshExtendedHistoryPattern = regexp.MustCompile(`^: [0-9]+:`)
 )
 
 const DefaultTermType = "xterm-256color"
@@ -74,6 +77,7 @@ const (
 	PwshIntegrationDir = "shell/pwsh"
 	FishIntegrationDir = "shell/fish"
 	WaveHomeBinDir     = "bin"
+	ZshHistoryFileName = ".zsh_history"
 )
 
 func DetectLocalShellPath() string {
@@ -208,6 +212,46 @@ func GetLocalZshZDotDir() string {
 	return filepath.Join(wavebase.GetWaveDataDir(), ZshIntegrationDir)
 }
 
+func HasWaveZshHistory() (bool, int64) {
+	zshDir := GetLocalZshZDotDir()
+	historyFile := filepath.Join(zshDir, ZshHistoryFileName)
+	fileInfo, err := os.Stat(historyFile)
+	if err != nil {
+		return false, 0
+	}
+	return true, fileInfo.Size()
+}
+
+func IsExtendedZshHistoryFile(fileName string) (bool, error) {
+	file, err := os.Open(fileName)
+	if err != nil {
+		if os.IsNotExist(err) {
+			return false, nil
+		}
+		return false, err
+	}
+	defer file.Close()
+
+	buf := make([]byte, 1024)
+	n, err := file.Read(buf)
+	if err != nil {
+		return false, err
+	}
+
+	content := string(buf[:n])
+	lines := strings.Split(content, "\n")
+
+	for _, line := range lines {
+		line = strings.TrimSpace(line)
+		if line == "" {
+			continue
+		}
+		return ZshExtendedHistoryPattern.MatchString(line), nil
+	}
+
+	return false, nil
+}
+
 func GetLocalWshBinaryPath(version string, goos string, goarch string) (string, error) {
 	ext := ""
 	if goarch == "amd64" {
@@ -422,6 +466,80 @@ func getShellVersion(shellPath string, shellType string) (string, error) {
 	return matches[1], nil
 }
 
+func FixupWaveZshHistory() error {
+	if runtime.GOOS != "darwin" {
+		return nil
+	}
+
+	hasHistory, size := HasWaveZshHistory()
+	if !hasHistory {
+		return nil
+	}
+
+	zshDir := GetLocalZshZDotDir()
+	waveHistFile := filepath.Join(zshDir, ZshHistoryFileName)
+
+	if size == 0 {
+		err := os.Remove(waveHistFile)
+		if err != nil {
+			log.Printf("error removing wave zsh history file %s: %v\n", waveHistFile, err)
+		}
+		return nil
+	}
+
+	log.Printf("merging wave zsh history %s into ~/.zsh_history\n", waveHistFile)
+
+	homeDir, err := os.UserHomeDir()
+	if err != nil {
+		return fmt.Errorf("error getting home directory: %w", err)
+	}
+	realHistFile := filepath.Join(homeDir, ".zsh_history")
+
+	isExtended, err := IsExtendedZshHistoryFile(realHistFile)
+	if err != nil {
+		return fmt.Errorf("error checking if history is extended: %w", err)
+	}
+
+	hasExtendedStr := "false"
+	if isExtended {
+		hasExtendedStr = "true"
+	}
+
+	quotedWaveHistFile := utilfn.ShellQuote(waveHistFile, true, -1)
+
+	script := fmt.Sprintf(`
+		HISTFILE=~/.zsh_history
+		HISTSIZE=999999
+		SAVEHIST=999999
+		has_extended_history=%s
+		[[ $has_extended_history == true ]] && setopt EXTENDED_HISTORY
+		fc -RI
+		fc -RI %s
+		fc -W
+	`, hasExtendedStr, quotedWaveHistFile)
+
+	ctx, cancelFn := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancelFn()
+
+	cmd := exec.CommandContext(ctx, "zsh", "-f", "-i", "-c", script)
+	cmd.Stdin = nil
+	envStr := envutil.SliceToEnv(os.Environ())
+	envStr = envutil.RmEnv(envStr, "ZDOTDIR")
+	cmd.Env = envutil.EnvToSlice(envStr)
+	output, err := cmd.CombinedOutput()
+	if err != nil {
+		return fmt.Errorf("error executing zsh history fixup script: %w, output: %s", err, string(output))
+	}
+
+	err = os.Remove(waveHistFile)
+	if err != nil {
+		log.Printf("error removing wave zsh history file %s: %v\n", waveHistFile, err)
+	}
+	log.Printf("successfully merged wave zsh history %s into ~/.zsh_history\n", waveHistFile)
+
+	return nil
+}
+
 func FormatOSC(oscNum int, parts ...string) string {
 	if len(parts) == 0 {
 		return fmt.Sprintf("\x1b]%d\x07", oscNum)
diff --git a/pkg/wcloud/wcloud.go b/pkg/wcloud/wcloud.go
index 9101b34469..455acd8944 100644
--- a/pkg/wcloud/wcloud.go
+++ b/pkg/wcloud/wcloud.go
@@ -214,11 +214,11 @@ func sendTEvents(clientId string) (int, error) {
 }
 
 func SendAllTelemetry(clientId string) error {
-	defer func() {
-		ctx, cancelFn := context.WithTimeout(context.Background(), 2*time.Second)
-		defer cancelFn()
-		telemetry.CleanOldTEvents(ctx)
-	}()
+	ctx, cancelFn := context.WithTimeout(context.Background(), 2*time.Second)
+	defer cancelFn()
+	if err := telemetry.CleanOldTEvents(ctx); err != nil {
+		log.Printf("error cleaning old telemetry events: %v\n", err)
+	}
 	if !telemetry.IsTelemetryEnabled() {
 		log.Printf("telemetry disabled, not sending\n")
 		return nil