diff --git a/src/cmd/initContainer.go b/src/cmd/initContainer.go
index 3c31d2a..03bb066 100644
--- a/src/cmd/initContainer.go
+++ b/src/cmd/initContainer.go
@@ -21,14 +21,13 @@ import (
 	"fmt"
 	"io/ioutil"
 	"os"
-	"os/exec"
 	"os/user"
 	"path/filepath"
 	"strings"
-	"syscall"
 
 	"github.com/containers/toolbox/pkg/shell"
 	"github.com/containers/toolbox/pkg/utils"
+	"github.com/fsnotify/fsnotify"
 	"github.com/sirupsen/logrus"
 	"github.com/spf13/cobra"
 )
@@ -177,6 +176,10 @@ func initContainer(cmd *cobra.Command, args []string) error {
 				}
 			}
 
+			if err := updateTimeZoneFromLocalTime(); err != nil {
+				return err
+			}
+
 			if _, err := os.Readlink("/etc/resolv.conf"); err != nil {
 				if err := redirectPath("/etc/resolv.conf",
 					"/run/host/etc/resolv.conf",
@@ -197,18 +200,6 @@ func initContainer(cmd *cobra.Command, args []string) error {
 				}
 			}
 		}
-
-		if utils.PathExists("/run/host/monitor") {
-			logrus.Debug("Path /run/host/monitor exists")
-
-			if _, err := os.Readlink("/etc/timezone"); err != nil {
-				if err := redirectPath("/etc/timezone",
-					"/run/host/monitor/timezone",
-					false); err != nil {
-					return err
-				}
-			}
-		}
 	}
 
 	if initContainerFlags.mediaLink {
@@ -267,6 +258,19 @@ func initContainer(cmd *cobra.Command, args []string) error {
 		}
 	}
 
+	logrus.Debug("Setting up watches for file system events")
+
+	watcherForHost, err := fsnotify.NewWatcher()
+	if err != nil {
+		return err
+	}
+
+	defer watcherForHost.Close()
+
+	if err := watcherForHost.Add("/run/host/etc"); err != nil {
+		return err
+	}
+
 	logrus.Debug("Finished initializing container")
 
 	toolboxRuntimeDirectory := runtimeDirectory + "/toolbox"
@@ -297,22 +301,15 @@ func initContainer(cmd *cobra.Command, args []string) error {
 		return errors.New("failed to change ownership of initialization stamp")
 	}
 
-	logrus.Debug("Going to sleep")
+	logrus.Debug("Listening to file system events")
 
-	sleepBinary, err := exec.LookPath("sleep")
-	if err != nil {
-		if errors.Is(err, exec.ErrNotFound) {
-			return errors.New("sleep(1) not found")
+	for {
+		select {
+		case event := <-watcherForHost.Events:
+			handleFileSystemEvent(event)
+		case err := <-watcherForHost.Errors:
+			logrus.Warnf("Received an error from the file system watcher: %v", err)
 		}
-
-		return errors.New("failed to lookup sleep(1)")
-	}
-
-	sleepArgs := []string{"sleep", "+Inf"}
-	env := os.Environ()
-
-	if err := syscall.Exec(sleepBinary, sleepArgs, env); err != nil {
-		return errors.New("failed to invoke sleep(1)")
 	}
 
 	return nil
@@ -410,6 +407,17 @@ func configureUsers(targetUserUid int,
 	return nil
 }
 
+func handleFileSystemEvent(event fsnotify.Event) {
+	eventOpString := event.Op.String()
+	logrus.Debugf("Handling file system event: operation %s on %s", eventOpString, event.Name)
+
+	if event.Name == "/run/host/etc/localtime" {
+		if err := updateTimeZoneFromLocalTime(); err != nil {
+			logrus.Warnf("Failed to handle changes to the host's /etc/localtime: %v", err)
+		}
+	}
+}
+
 func mountBind(containerPath, source, flags string) error {
 	fi, err := os.Stat(source)
 	if err != nil {
@@ -555,3 +563,39 @@ func sanitizeRedirectionTarget(target string) string {
 
 	return target
 }
+
+func updateTimeZoneFromLocalTime() error {
+	localTimeEvaled, err := filepath.EvalSymlinks("/etc/localtime")
+	if err != nil {
+		return fmt.Errorf("failed to resolve /etc/localtime: %w", err)
+	}
+
+	logrus.Debugf("Resolved /etc/localtime to %s", localTimeEvaled)
+
+	const zoneInfoRoot = "/run/host/usr/share/zoneinfo"
+
+	if !strings.HasPrefix(localTimeEvaled, zoneInfoRoot) {
+		return errors.New("/etc/localtime points to unknown location")
+	}
+
+	timeZone, err := filepath.Rel(zoneInfoRoot, localTimeEvaled)
+	if err != nil {
+		return fmt.Errorf("failed to extract time zone: %w", err)
+	}
+
+	const etcTimeZone = "/etc/timezone"
+
+	if err := os.Remove(etcTimeZone); err != nil {
+		if !os.IsNotExist(err) {
+			return fmt.Errorf("failed to remove old %s: %w", etcTimeZone, err)
+		}
+	}
+
+	timeZoneBytes := []byte(timeZone + "\n")
+	err = ioutil.WriteFile(etcTimeZone, timeZoneBytes, 0664)
+	if err != nil {
+		return fmt.Errorf("failed to create new %s: %w", etcTimeZone, err)
+	}
+
+	return nil
+}
diff --git a/src/go.mod b/src/go.mod
index 2b1ac30..823b8d9 100644
--- a/src/go.mod
+++ b/src/go.mod
@@ -7,6 +7,7 @@ require (
 	github.com/acobaugh/osrelease v0.0.0-20181218015638-a93a0a55a249
 	github.com/briandowns/spinner v1.10.0
 	github.com/docker/go-units v0.4.0
+	github.com/fsnotify/fsnotify v1.4.7
 	github.com/godbus/dbus/v5 v5.0.3
 	github.com/sirupsen/logrus v1.4.2
 	github.com/spf13/cobra v0.0.5
diff --git a/src/go.sum b/src/go.sum
index 4d6a003..5a03a68 100644
--- a/src/go.sum
+++ b/src/go.sum
@@ -16,6 +16,7 @@ github.com/docker/go-units v0.4.0 h1:3uh0PgVws3nIA0Q+MwDC8yjEPf9zjRfZZWXZYDct3Tw
 github.com/docker/go-units v0.4.0/go.mod h1:fgPhTUdO+D/Jk86RDLlptpiXQzgHJF7gydDDbaIK4Dk=
 github.com/fatih/color v1.7.0 h1:DkWD4oS2D8LGGgTQ6IvwJJXSL5Vp2ffcQg58nFV38Ys=
 github.com/fatih/color v1.7.0/go.mod h1:Zm6kSWBoL9eyXnKyktHP6abPY2pDugNf5KwzbycvMj4=
+github.com/fsnotify/fsnotify v1.4.7 h1:IXs+QLmnXW2CcXuY+8Mzv/fWEsPGWxqefPtCP5CnV9I=
 github.com/fsnotify/fsnotify v1.4.7/go.mod h1:jwhsz4b93w/PPRr/qN1Yymfu8t87LnFCMoQvtojpjFo=
 github.com/godbus/dbus/v5 v5.0.3 h1:ZqHaoEF7TBzh4jzPmqVhE/5A1z9of6orkAe5uHoAeME=
 github.com/godbus/dbus/v5 v5.0.3/go.mod h1:xhWf0FNVPg57R7Z0UbKHbJfkEywrmjJnf7w5xrFpKfA=
diff --git a/test/system/helpers.bash b/test/system/helpers.bash
index 497b35c..d7e5162 100644
--- a/test/system/helpers.bash
+++ b/test/system/helpers.bash
@@ -113,7 +113,7 @@ function run_toolbox() {
 
 function is_toolbox_ready() {
     toolbox_container="$1"
-    expected_string="Going to sleep"
+    expected_string="Listening to file system events"
     num_of_tries=5
     timeout=2