diff --git a/clap_generate/examples/value_hints.rs b/clap_generate/examples/value_hints.rs
index e475d2c7a0c3..5389a913c673 100644
--- a/clap_generate/examples/value_hints.rs
+++ b/clap_generate/examples/value_hints.rs
@@ -69,7 +69,9 @@ fn build_cli() -> App<'static> {
                 .value_hint(ValueHint::CommandString),
         )
         .arg(
-            Arg::with_name("command_with_args").multiple(true), // .value_hint(ValueHint::CommandWithArguments),
+            Arg::with_name("command_with_args")
+                .multiple_values(true)
+                .value_hint(ValueHint::CommandWithArguments),
         )
         .arg(
             Arg::with_name("user")
diff --git a/src/build/app/mod.rs b/src/build/app/mod.rs
index 76d2aabc48dd..f496e1196ce3 100644
--- a/src/build/app/mod.rs
+++ b/src/build/app/mod.rs
@@ -25,7 +25,7 @@ use crate::output::{Help, Usage};
 use crate::parse::errors::Result as ClapResult;
 use crate::parse::{ArgMatcher, ArgMatches, Input, Parser};
 use crate::util::{Id, Key};
-use crate::INTERNAL_ERROR_MSG;
+use crate::{ValueHint, INTERNAL_ERROR_MSG};
 
 // FIXME (@CreepySkeleton): some of this variants are never constructed
 #[derive(Clone, Debug, PartialEq, Eq)]
@@ -1665,6 +1665,20 @@ impl<'b> App<'b> {
                 "Global arguments cannot be required.\n\n\t'{}' is marked as global and required",
                 arg.name
             );
+
+            if arg.value_hint == ValueHint::CommandWithArguments {
+                assert!(
+                    arg.short.is_none() && arg.long.is_none(),
+                    "Argument '{}' has hint CommandWithArguments and must be positional.",
+                    arg.name
+                );
+
+                assert!(
+                    self.is_set(AppSettings::TrailingVarArg),
+                    "Positional argument '{}' has hint CommandWithArguments, so App must have TrailingVarArg set.",
+                    arg.name
+                );
+            }
         }
 
         for group in &self.groups {
diff --git a/src/build/arg/mod.rs b/src/build/arg/mod.rs
index 64aa781f310e..209eb26f4311 100644
--- a/src/build/arg/mod.rs
+++ b/src/build/arg/mod.rs
@@ -4208,6 +4208,21 @@ impl<'a> Arg<'a> {
                 self.name,
             );
         }
+
+        if self.value_hint != ValueHint::Unknown {
+            assert!(
+                self.is_set(ArgSettings::TakesValue),
+                "Argument '{}' has value hint but takes no value",
+                self.name
+            );
+
+            if self.value_hint == ValueHint::CommandWithArguments {
+                assert!(
+                    self.is_set(ArgSettings::MultipleValues),
+                    "Argument '{}' uses hint CommandWithArguments and must accept multiple values",
+                )
+            }
+        }
     }
 }