diff --git a/plumbum/cli/switches.py b/plumbum/cli/switches.py
index e6db1bb9..3321d778 100644
--- a/plumbum/cli/switches.py
+++ b/plumbum/cli/switches.py
@@ -464,10 +464,16 @@ class MyApp(Application):
                              comparison or not. The default is ``False``
     :param csv: splits the input as a comma-separated-value before validating and returning
                 a list. Accepts ``True``, ``False``, or a string for the separator
-    """
+    :param all_markers: when a user inputs any value from this set, it is considered that
+                        he requested iteration over all values. By default `all_markers`
+                        are {"*", "all"}."""
 
     def __init__(self, *values, **kwargs):
         self.case_sensitive = kwargs.pop("case_sensitive", False)
+        all_markers = kwargs.pop("all_markers", None)
+        if all_markers is None:
+            all_markers = {"*", "all"} - set(values)
+        self.all_markers = frozenset(all_markers)
         self.csv = kwargs.pop("csv", False)
         if self.csv is True:
             self.csv = ","
@@ -475,7 +481,30 @@ def __init__(self, *values, **kwargs):
             raise TypeError(
                 _("got unexpected keyword argument(s): {0}").format(kwargs.keys())
             )
-        self.values = values
+
+        str_values = []
+        numeric_values = []
+        non_primitive_values = []
+        for opt in values:
+            if isinstance(opt, str):
+                if not self.case_sensitive:
+                    opt = opt.lower()
+                str_values.append(opt)
+            elif isinstance(opt, (int, float)):
+                numeric_values.append(opt)
+            else:
+                non_primitive_values.append(opt)
+        self.str_values = frozenset(str_values)
+        self.numeric_values = frozenset(numeric_values)
+        self.non_primitive_values = tuple(non_primitive_values)
+
+    @property
+    def primitive_values(self):
+        return self.str_values | self.numeric_values
+
+    @property
+    def values(self):
+        return tuple(self.primitive_values) + self.non_primitive_values
 
     def __repr__(self):
         return "{{{0}}}".format(
@@ -484,16 +513,29 @@ def __repr__(self):
 
     def __call__(self, value, check_csv=True):
         if self.csv and check_csv:
-            return [self(v.strip(), check_csv=False) for v in value.split(",")]
+            vals = value.split(",")
+            res = []
+            for v in vals:
+                if v in self.all_markers:
+                    res.extend(self.primitive_values)
+                else:
+                    res.append(self(v.strip(), check_csv=False))
+
+            return res
+
         if not self.case_sensitive:
             value = value.lower()
-        for opt in self.values:
-            if isinstance(opt, str):
-                if not self.case_sensitive:
-                    opt = opt.lower()
-                if opt == value:
-                    return opt  # always return original value
-                continue
+
+        try:
+            if value in self.str_values:
+                return value
+
+            if value in self.numeric_values:
+                return value
+        except TypeError:
+            pass
+
+        for opt in self.non_primitive_values:
             try:
                 return opt(value)
             except ValueError:
@@ -503,11 +545,16 @@ def __call__(self, value, check_csv=True):
         )
 
     def choices(self, partial=""):
-        choices = {
-            opt if isinstance(opt, str) else "({})".format(opt) for opt in self.values
-        }
+        choices = (
+            self.all_markers
+            | self.str_values
+            | {"({})".format(opt) for opt in self.numeric_values}
+            | {"({})".format(opt) for opt in self.primitive_values}
+        )
+
         if partial:
             choices = {opt for opt in choices if opt.lower().startswith(partial)}
+
         return choices
 
 
diff --git a/tests/test_cli.py b/tests/test_cli.py
index bb32c5e4..e3193d50 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -197,6 +197,9 @@ def test_okay(self):
         _, rc = SimpleApp.run(["foo", "--bacon=81", "--csv=MAX,MIN,100"], exit=False)
         assert rc == 0
 
+        _, rc = SimpleApp.run(["foo", "--bacon=81", "--csv=all,100"], exit=False)
+        assert rc == 0
+
         _, rc = SimpleApp.run(["foo", "--bacon=81", "--num=100"], exit=False)
         assert rc == 0