diff --git a/crates/bevy_ecs/src/schedule/executor/mod.rs b/crates/bevy_ecs/src/schedule/executor/mod.rs
index 710b88db6c23f..9e22de29f3f62 100644
--- a/crates/bevy_ecs/src/schedule/executor/mod.rs
+++ b/crates/bevy_ecs/src/schedule/executor/mod.rs
@@ -304,7 +304,7 @@ mod tests {
     use crate::{
         prelude::{Component, In, IntoSystem, Resource, Schedule},
         schedule::ExecutorKind,
-        system::{Populated, Res, ResMut, Single},
+        system::{Populated, Res, ResMut, Single, When},
         world::World,
     };
 
@@ -327,12 +327,12 @@ mod tests {
     #[derive(Resource, Default)]
     struct Counter(u8);
 
-    fn set_single_state(mut _single: Single<&TestComponent>, mut state: ResMut<TestState>) {
+    fn set_single_state(mut _single: When<Single<&TestComponent>>, mut state: ResMut<TestState>) {
         state.single_ran = true;
     }
 
     fn set_populated_state(
-        mut _populated: Populated<&TestComponent>,
+        mut _populated: When<Populated<&TestComponent>>,
         mut state: ResMut<TestState>,
     ) {
         state.populated_ran = true;
@@ -404,7 +404,7 @@ mod tests {
     #[test]
     fn piped_systems_first_system_skipped() {
         // This system should be skipped when run due to no matching entity
-        fn pipe_out(_single: Single<&TestComponent>) -> u8 {
+        fn pipe_out(_single: When<Single<&TestComponent>>) -> u8 {
             42
         }
 
@@ -431,7 +431,7 @@ mod tests {
         }
 
         // This system should be skipped when run due to no matching entity
-        fn pipe_in(_input: In<u8>, _single: Single<&TestComponent>) {}
+        fn pipe_in(_input: In<u8>, _single: When<Single<&TestComponent>>) {}
 
         let mut world = World::new();
         world.init_resource::<Counter>();
@@ -482,7 +482,7 @@ mod tests {
     #[test]
     fn piped_system_skip_and_panic() {
         // This system should be skipped when run due to no matching entity
-        fn pipe_out(_single: Single<&TestComponent>) -> u8 {
+        fn pipe_out(_single: When<Single<&TestComponent>>) -> u8 {
             42
         }
 
@@ -506,7 +506,7 @@ mod tests {
         }
 
         // This system should be skipped when run due to no matching entity
-        fn pipe_in(_input: In<u8>, _single: Single<&TestComponent>) {}
+        fn pipe_in(_input: In<u8>, _single: When<Single<&TestComponent>>) {}
 
         let mut world = World::new();
         let mut schedule = Schedule::default();
@@ -538,13 +538,17 @@ mod tests {
     fn piped_system_skip_and_skip() {
         // This system should be skipped when run due to no matching entity
 
-        fn pipe_out(_single: Single<&TestComponent>, mut counter: ResMut<Counter>) -> u8 {
+        fn pipe_out(_single: When<Single<&TestComponent>>, mut counter: ResMut<Counter>) -> u8 {
             counter.0 += 1;
             42
         }
 
         // This system should be skipped when run due to no matching entity
-        fn pipe_in(_input: In<u8>, _single: Single<&TestComponent>, mut counter: ResMut<Counter>) {
+        fn pipe_in(
+            _input: In<u8>,
+            _single: When<Single<&TestComponent>>,
+            mut counter: ResMut<Counter>,
+        ) {
             counter.0 += 1;
         }
 
diff --git a/crates/bevy_ecs/src/system/query.rs b/crates/bevy_ecs/src/system/query.rs
index dfc07d23f1bb0..31cbc40578a43 100644
--- a/crates/bevy_ecs/src/system/query.rs
+++ b/crates/bevy_ecs/src/system/query.rs
@@ -2566,9 +2566,11 @@ impl<'w, 'q, Q: QueryData, F: QueryFilter> From<&'q mut Query<'w, '_, Q, F>>
 /// [System parameter] that provides access to single entity's components, much like [`Query::single`]/[`Query::single_mut`].
 ///
 /// This [`SystemParam`](crate::system::SystemParam) fails validation if zero or more than one matching entity exists.
-/// This will cause the system to be skipped, according to the rules laid out in [`SystemParamValidationError`](crate::system::SystemParamValidationError).
+/// This will cause the system to fail, according to the rules laid out in [`SystemParamValidationError`](crate::system::SystemParamValidationError).
 ///
-/// Use [`Option<Single<D, F>>`] instead if zero or one matching entities can exist.
+/// Use [`Option<Single<D, F>>`] instead to run the system but get `None` when there are zero or multiple matching entities.
+///
+/// Use [`When<Single<D, F>>`](crate::system::When) instead to skip the system when there are zero or multiple matching entities.
 ///
 /// See [`Query`] for more details.
 ///
@@ -2617,7 +2619,9 @@ impl<'w, D: QueryData, F: QueryFilter> Single<'w, D, F> {
 /// [System parameter] that works very much like [`Query`] except it always contains at least one matching entity.
 ///
 /// This [`SystemParam`](crate::system::SystemParam) fails validation if no matching entities exist.
-/// This will cause the system to be skipped, according to the rules laid out in [`SystemParamValidationError`](crate::system::SystemParamValidationError).
+/// This will cause the system to fail, according to the rules laid out in [`SystemParamValidationError`](crate::system::SystemParamValidationError).
+///
+/// Use [`When<Populated<D, F>>`](crate::system::When) instead to skip the system when there are zero matching entities.
 ///
 /// Much like [`Query::is_empty`] the worst case runtime will be `O(n)` where `n` is the number of *potential* matches.
 /// This can be notably expensive for queries that rely on non-archetypal filters such as [`Added`](crate::query::Added),
diff --git a/crates/bevy_ecs/src/system/system_param.rs b/crates/bevy_ecs/src/system/system_param.rs
index 8f36e6a8c28b9..93ad51aa156e9 100644
--- a/crates/bevy_ecs/src/system/system_param.rs
+++ b/crates/bevy_ecs/src/system/system_param.rs
@@ -441,10 +441,10 @@ unsafe impl<'a, D: QueryData + 'static, F: QueryFilter + 'static> SystemParam fo
         match query.single_inner() {
             Ok(_) => Ok(()),
             Err(QuerySingleError::NoEntities(_)) => Err(
-                SystemParamValidationError::skipped::<Self>("No matching entities"),
+                SystemParamValidationError::invalid::<Self>("No matching entities"),
             ),
             Err(QuerySingleError::MultipleEntities(_)) => Err(
-                SystemParamValidationError::skipped::<Self>("Multiple matching entities"),
+                SystemParamValidationError::invalid::<Self>("Multiple matching entities"),
             ),
         }
     }
@@ -502,7 +502,7 @@ unsafe impl<D: QueryData + 'static, F: QueryFilter + 'static> SystemParam
             state.query_unchecked_with_ticks(world, system_meta.last_run, world.change_tick())
         };
         if query.is_empty() {
-            Err(SystemParamValidationError::skipped::<Self>(
+            Err(SystemParamValidationError::invalid::<Self>(
                 "No matching entities",
             ))
         } else {
@@ -1827,6 +1827,8 @@ unsafe impl<T: ReadOnlySystemParam> ReadOnlySystemParam for Result<T, SystemPara
 
 /// A [`SystemParam`] that wraps another parameter and causes its system to skip instead of failing when the parameter is invalid.
 ///
+/// This is especially useful with [`Single`] and [`Populated`].
+///
 /// # Example
 ///
 /// ```
@@ -2794,12 +2796,6 @@ pub struct SystemParamValidationError {
 }
 
 impl SystemParamValidationError {
-    /// Constructs a `SystemParamValidationError` that skips the system.
-    /// The parameter name is initialized to the type name of `T`, so a `SystemParam` should usually pass `Self`.
-    pub fn skipped<T>(message: impl Into<Cow<'static, str>>) -> Self {
-        Self::new::<T>(true, message, Cow::Borrowed(""))
-    }
-
     /// Constructs a `SystemParamValidationError` for an invalid parameter that should be treated as an error.
     /// The parameter name is initialized to the type name of `T`, so a `SystemParam` should usually pass `Self`.
     pub fn invalid<T>(message: impl Into<Cow<'static, str>>) -> Self {
diff --git a/crates/bevy_input_focus/src/lib.rs b/crates/bevy_input_focus/src/lib.rs
index d146b1cc56264..9235ae56ff6b0 100644
--- a/crates/bevy_input_focus/src/lib.rs
+++ b/crates/bevy_input_focus/src/lib.rs
@@ -221,10 +221,10 @@ pub type InputFocusSet = InputFocusSystems;
 /// If no entity is focused, sets the focus to the primary window, if any.
 pub fn set_initial_focus(
     mut input_focus: ResMut<InputFocus>,
-    window: Single<Entity, With<PrimaryWindow>>,
+    window: When<Single<Entity, With<PrimaryWindow>>>,
 ) {
     if input_focus.0.is_none() {
-        input_focus.0 = Some(*window);
+        input_focus.0 = Some(**window);
     }
 }
 
diff --git a/examples/ecs/fallible_params.rs b/examples/ecs/fallible_params.rs
index 94a8007aec090..6a32e66c500b9 100644
--- a/examples/ecs/fallible_params.rs
+++ b/examples/ecs/fallible_params.rs
@@ -119,8 +119,8 @@ fn user_input(
 
 // System that moves the enemies in a circle.
 // Only runs if there are enemies, due to the `Populated` parameter.
-fn move_targets(mut enemies: Populated<(&mut Transform, &mut Enemy)>, time: Res<Time>) {
-    for (mut transform, mut target) in &mut *enemies {
+fn move_targets(mut enemies: When<Populated<(&mut Transform, &mut Enemy)>>, time: Res<Time>) {
+    for (mut transform, mut target) in &mut **enemies {
         target.rotation += target.rotation_speed * time.delta_secs();
         transform.rotation = Quat::from_rotation_z(target.rotation);
         let offset = transform.right() * target.radius;
@@ -160,4 +160,4 @@ fn track_targets(
 
 /// This system always fails param validation, because we never
 /// create an entity with both [`Player`] and [`Enemy`] components.
-fn do_nothing_fail_validation(_: Single<(), (With<Player>, With<Enemy>)>) {}
+fn do_nothing_fail_validation(_: When<Single<(), (With<Player>, With<Enemy>)>>) {}
diff --git a/release-content/migration-guides/single_and_populated_fail.md b/release-content/migration-guides/single_and_populated_fail.md
new file mode 100644
index 0000000000000..a19ef763370b6
--- /dev/null
+++ b/release-content/migration-guides/single_and_populated_fail.md
@@ -0,0 +1,14 @@
+---
+title: "`Single` and `Populated` now fail instead of skipping"
+pull_requests: [19489, 18765]
+---
+
+`Single<D, F>` and `Populated<D, F>` now cause systems to fail instead of skip.
+
+The introduction of `When` makes it possible to skip systems for any invalid parameter, such as `When<Res<R>>`.
+The change to the behavior of `Single` and `Populated` keeps them consistent with other parameters,
+and makes it possible to use them as assertions instead of only as run conditions.
+
+Replace `Single<D, F>` with `When<Single<D, F>>`
+and `Populated<D, F>` with `When<Populated<D, F>>`
+to restore the old behavior.