diff --git a/clap_builder/src/builder/arg.rs b/clap_builder/src/builder/arg.rs
index f83b4642c16..1a1bdb134a3 100644
--- a/clap_builder/src/builder/arg.rs
+++ b/clap_builder/src/builder/arg.rs
@@ -4078,7 +4078,9 @@ impl Arg {
     }
 
     pub(crate) fn is_takes_value_set(&self) -> bool {
-        self.get_action().takes_values()
+        self.get_num_args()
+            .unwrap_or_else(|| 1.into())
+            .takes_values()
     }
 
     /// Report whether [`Arg::allow_hyphen_values`] is set
diff --git a/clap_builder/src/builder/debug_asserts.rs b/clap_builder/src/builder/debug_asserts.rs
index 2b633849fbe..bfb491f5475 100644
--- a/clap_builder/src/builder/debug_asserts.rs
+++ b/clap_builder/src/builder/debug_asserts.rs
@@ -704,13 +704,14 @@ fn assert_arg(arg: &Arg) {
         arg.get_id(),
     );
 
-    assert_eq!(
-        arg.get_action().takes_values(),
-        arg.is_takes_value_set(),
-        "Argument `{}`'s selected action {:?} contradicts `takes_value`",
-        arg.get_id(),
-        arg.get_action()
-    );
+    if arg.is_takes_value_set() {
+        assert!(
+            arg.get_action().takes_values(),
+            "Argument `{}`'s selected action {:?} contradicts `takes_value`",
+            arg.get_id(),
+            arg.get_action()
+        );
+    }
     if let Some(action_type_id) = arg.get_action().value_type_id() {
         assert_eq!(
             action_type_id,
@@ -774,13 +775,6 @@ fn assert_arg(arg: &Arg) {
         }
     }
 
-    assert_eq!(
-        num_vals.takes_values(),
-        arg.is_takes_value_set(),
-        "Argument {}: mismatch between `num_args` ({}) and `takes_value`",
-        arg.get_id(),
-        num_vals,
-    );
     assert_eq!(
         num_vals.is_multiple(),
         arg.is_multiple_values_set(),
diff --git a/clap_mangen/src/render.rs b/clap_mangen/src/render.rs
index ef4981d80d6..11b8c5dec41 100644
--- a/clap_mangen/src/render.rs
+++ b/clap_mangen/src/render.rs
@@ -99,7 +99,7 @@ pub(crate) fn options(roff: &mut Roff, cmd: &clap::Command) {
             (None, None) => vec![],
         };
 
-        if opt.get_action().takes_values() {
+        if opt.get_num_args().expect("built").takes_values() {
             if let Some(value) = &opt.get_value_names() {
                 header.push(roman("="));
                 header.push(italic(value.join(" ")));
@@ -288,7 +288,7 @@ fn option_environment(opt: &clap::Arg) -> Option<Vec<Inline>> {
 }
 
 fn option_default_values(opt: &clap::Arg) -> Option<String> {
-    if opt.is_hide_default_value_set() || !opt.get_action().takes_values() {
+    if opt.is_hide_default_value_set() || !opt.get_num_args().expect("built").takes_values() {
         return None;
     } else if !opt.get_default_values().is_empty() {
         let values = opt
diff --git a/examples/find.md b/examples/find.md
index e9b1a86f89a..c52cbd391ce 100644
--- a/examples/find.md
+++ b/examples/find.md
@@ -12,7 +12,7 @@ Options:
 
 TESTS:
       --empty        File is empty and is either a regular file or a directory
-      --name <NAME>  Base of file name (the path with the leading directories removed) matches shell
+      --name <name>  Base of file name (the path with the leading directories removed) matches shell
                      pattern pattern
 
 OPERATORS:
@@ -41,5 +41,39 @@ $ find --empty -o --name .keep
     ),
 ]
 
+$ find --empty -o --name .keep -o --name foo
+[
+    (
+        "empty",
+        Bool(
+            true,
+        ),
+    ),
+    (
+        "or",
+        Bool(
+            true,
+        ),
+    ),
+    (
+        "name",
+        String(
+            ".keep",
+        ),
+    ),
+    (
+        "or",
+        Bool(
+            true,
+        ),
+    ),
+    (
+        "name",
+        String(
+            "foo",
+        ),
+    ),
+]
+
 ```
 
diff --git a/examples/find.rs b/examples/find.rs
index 0b7f2c70000..61ce066f4dc 100644
--- a/examples/find.rs
+++ b/examples/find.rs
@@ -1,6 +1,6 @@
 use std::collections::BTreeMap;
 
-use clap::{arg, command, ArgGroup, ArgMatches, Command};
+use clap::{command, value_parser, Arg, ArgAction, ArgGroup, ArgMatches, Command};
 
 fn main() {
     let matches = cli().get_matches();
@@ -13,17 +13,44 @@ fn cli() -> Command {
         .group(ArgGroup::new("tests").multiple(true))
         .next_help_heading("TESTS")
         .args([
-            arg!(--empty "File is empty and is either a regular file or a directory").group("tests"),
-            arg!(--name <NAME> "Base of file name (the path with the leading directories removed) matches shell pattern pattern").group("tests"),
+            position_sensitive_flag(Arg::new("empty"))
+                .long("empty")
+                .action(ArgAction::Append)
+                .help("File is empty and is either a regular file or a directory")
+                .group("tests"),
+            Arg::new("name")
+                .long("name")
+                .action(ArgAction::Append)
+                .help("Base of file name (the path with the leading directories removed) matches shell pattern pattern")
+                .group("tests")
         ])
         .group(ArgGroup::new("operators").multiple(true))
         .next_help_heading("OPERATORS")
         .args([
-            arg!(-o - -or "expr2 is not evaluate if exp1 is true").group("operators"),
-            arg!(-a - -and "Same as `expr1 expr1`").group("operators"),
+            position_sensitive_flag(Arg::new("or"))
+                .short('o')
+                .long("or")
+                .action(ArgAction::Append)
+                .help("expr2 is not evaluate if exp1 is true")
+                .group("operators"),
+            position_sensitive_flag(Arg::new("and"))
+                .short('a')
+                .long("and")
+                .action(ArgAction::Append)
+                .help("Same as `expr1 expr1`")
+                .group("operators"),
         ])
 }
 
+fn position_sensitive_flag(arg: Arg) -> Arg {
+    // Flags don't track the position of each occurrence, so we need to emulate flags with
+    // value-less options to get the same result
+    arg.num_args(0)
+        .value_parser(value_parser!(bool))
+        .default_missing_value("true")
+        .default_value("false")
+}
+
 #[derive(Clone, PartialEq, Eq, Hash, Debug)]
 pub enum Value {
     Bool(bool),