diff --git a/cmd/run.go b/cmd/run.go
index d2289d97f..017308d02 100644
--- a/cmd/run.go
+++ b/cmd/run.go
@@ -220,6 +220,16 @@ func run(args []string) error {
 		logrus.Warn("Consider recreating it with Toolbox version 0.0.17 or newer")
 	}
 
+	logrus.Info("Checking if the current working directory is in the container")
+	args = []string{"exec",
+		"--user", viper.GetString("USER"),
+		containerName,
+		"sh", "-c", fmt.Sprintf("test -d %s", viper.GetString("PWD"))}
+	err = podman.CmdRun(args...)
+	if err != nil {
+		logrus.Fatalf("Directory '%s' does not exist in container '%s', try running 'cd && !!'", viper.GetString("PWD"), containerName)
+	}
+
 	logrus.Infof("Looking for program '%s' in container %s", commands[0], containerName)
 
 	args = []string{"exec",
diff --git a/toolbox.sh b/toolbox.sh
index 8726f255e..6bfb5392f 100755
--- a/toolbox.sh
+++ b/toolbox.sh
@@ -1581,6 +1581,14 @@ run()
         fi
     fi
 
+    if ! $podman_command exec \
+                 --user "$USER" \
+                 "$toolbox_container" \
+                 sh -c "test -d $PWD" >/dev/null 2>&3; then
+        echo "Directory $PWD does not exist in container $toolbox_container, try cd && !!" >&2
+        exit 127
+    fi
+
     echo "$base_toolbox_command: running in container $toolbox_container:" >&3
     echo "$base_toolbox_command: $program" >&3
     for i in "$@"; do