diff --git a/components/style/dom.rs b/components/style/dom.rs
index 9a81e2ec774..633dce83655 100644
--- a/components/style/dom.rs
+++ b/components/style/dom.rs
@@ -801,24 +801,29 @@ pub trait TElement:
     {
         use rule_collector::containing_shadow_ignoring_svg_use;
 
-        let mut doc_rules_apply = self.matches_user_and_author_rules();
+        let target = self.rule_hash_target();
+        if !target.matches_user_and_author_rules() {
+            return false;
+        }
+
+        let mut doc_rules_apply = true;
 
         // Use the same rules to look for the containing host as we do for rule
         // collection.
-        if let Some(shadow) = containing_shadow_ignoring_svg_use(*self) {
+        if let Some(shadow) = containing_shadow_ignoring_svg_use(target) {
             doc_rules_apply = false;
             if let Some(data) = shadow.style_data() {
                 f(data, shadow.host());
             }
         }
 
-        if let Some(shadow) = self.shadow_root() {
+        if let Some(shadow) = target.shadow_root() {
             if let Some(data) = shadow.style_data() {
                 f(data, shadow.host());
             }
         }
 
-        let mut current = self.assigned_slot();
+        let mut current = target.assigned_slot();
         while let Some(slot) = current {
             // Slots can only have assigned nodes when in a shadow tree.
             let shadow = slot.containing_shadow().unwrap();
diff --git a/components/style/gecko/wrapper.rs b/components/style/gecko/wrapper.rs
index 9d987c56308..cec55130c4a 100644
--- a/components/style/gecko/wrapper.rs
+++ b/components/style/gecko/wrapper.rs
@@ -1405,7 +1405,7 @@ impl<'le> TElement for GeckoElement<'le> {
 
     #[inline]
     fn matches_user_and_author_rules(&self) -> bool {
-        !self.rule_hash_target().is_in_native_anonymous_subtree()
+        !self.is_in_native_anonymous_subtree()
     }
 
     #[inline]
diff --git a/components/style/rule_collector.rs b/components/style/rule_collector.rs
index e87a86c5e47..2e8ffe5d858 100644
--- a/components/style/rule_collector.rs
+++ b/components/style/rule_collector.rs
@@ -13,7 +13,7 @@ use crate::selector_parser::PseudoElement;
 use crate::shared_lock::Locked;
 use crate::stylesheets::Origin;
 use crate::stylist::{AuthorStylesEnabled, Rule, RuleInclusion, Stylist};
-use selectors::matching::{ElementSelectorFlags, MatchingContext};
+use selectors::matching::{ElementSelectorFlags, MatchingContext, MatchingMode};
 use servo_arc::ArcBorrow;
 use smallvec::SmallVec;
 
@@ -97,8 +97,16 @@ where
         context: &'a mut MatchingContext<'b, E::Impl>,
         flags_setter: &'a mut F,
     ) -> Self {
-        let rule_hash_target = element.rule_hash_target();
-        let matches_user_and_author_rules = element.matches_user_and_author_rules();
+        // When we're matching with matching_mode =
+        // `ForStatelessPseudoeElement`, the "target" for the rule hash is the
+        // element itself, since it's what's generating the pseudo-element.
+        let rule_hash_target = match context.matching_mode() {
+            MatchingMode::ForStatelessPseudoElement => element,
+            MatchingMode::Normal => element.rule_hash_target(),
+        };
+
+        let matches_user_and_author_rules =
+            rule_hash_target.matches_user_and_author_rules();
 
         // Gecko definitely has pseudo-elements with style attributes, like
         // ::-moz-color-swatch.
@@ -120,8 +128,8 @@ where
             context,
             flags_setter,
             rules,
-            matches_user_and_author_rules,
             shadow_cascade_order: 0,
+            matches_user_and_author_rules,
             matches_document_author_rules: matches_user_and_author_rules,
         }
     }
diff --git a/components/style/stylist.rs b/components/style/stylist.rs
index 2953e3f0671..cba1cbac524 100644
--- a/components/style/stylist.rs
+++ b/components/style/stylist.rs
@@ -1195,6 +1195,10 @@ impl Stylist {
         // See [3] for the bug to implement whatever gets resolved, and related
         // bugs for a bit more context.
         //
+        // FIXME(emilio): This should probably work for pseudo-elements (i.e.,
+        // use rule_hash_target().shadow_root() instead of
+        // element.shadow_root()).
+        //
         // [1]: https://cs.chromium.org/chromium/src/third_party/blink/renderer/
         //        core/css/resolver/style_resolver.cc?l=1267&rcl=90f9f8680ebb4a87d177f3b0833372ae4e0c88d8
         // [2]: https://github.com/w3c/csswg-drafts/issues/1995