diff --git a/Userland/Libraries/LibWeb/CSS/StyleComputer.cpp b/Userland/Libraries/LibWeb/CSS/StyleComputer.cpp
index fc78d42668a..0496ee7d5c4 100644
--- a/Userland/Libraries/LibWeb/CSS/StyleComputer.cpp
+++ b/Userland/Libraries/LibWeb/CSS/StyleComputer.cpp
@@ -1410,7 +1410,11 @@ void StyleComputer::collect_animation_into(DOM::Element& element, Optional<CSS::
     }
 }
 
-static void apply_animation_properties(DOM::Document& document, StyleProperties& style, Animations::Animation& animation)
+enum class AnimationIsNew {
+    Yes,
+    No,
+};
+static void apply_animation_properties(DOM::Document& document, StyleProperties& style, Animations::Animation& animation, AnimationIsNew animation_is_new)
 {
     auto& effect = verify_cast<Animations::KeyframeEffect>(*animation.effect());
 
@@ -1468,10 +1472,12 @@ static void apply_animation_properties(DOM::Document& document, StyleProperties&
     effect.set_fill_mode(Animations::css_fill_mode_to_bindings_fill_mode(fill_mode));
     effect.set_playback_direction(Animations::css_animation_direction_to_bindings_playback_direction(direction));
 
-    HTML::TemporaryExecutionContext context(document.relevant_settings_object());
-    if (play_state == CSS::AnimationPlayState::Running && !animation.is_relevant()) {
+    // If this is a new animation, we always want to play it
+    if (play_state == CSS::AnimationPlayState::Running && (animation_is_new == AnimationIsNew::Yes || animation.play_state() == Bindings::AnimationPlayState::Paused)) {
+        HTML::TemporaryExecutionContext context(document.relevant_settings_object());
         animation.play().release_value_but_fixme_should_propagate_errors();
     } else if (play_state == CSS::AnimationPlayState::Paused && animation.play_state() != Bindings::AnimationPlayState::Paused) {
+        HTML::TemporaryExecutionContext context(document.relevant_settings_object());
         animation.pause().release_value_but_fixme_should_propagate_errors();
     }
 }
@@ -1553,7 +1559,7 @@ void StyleComputer::compute_cascaded_values(StyleProperties& style, DOM::Element
                 animation->set_timeline(m_document->timeline());
                 animation->set_owning_element(element);
                 animation->set_effect(effect);
-                apply_animation_properties(m_document, style, animation);
+                apply_animation_properties(m_document, style, animation, AnimationIsNew::Yes);
                 if (pseudo_element.has_value())
                     effect->set_pseudo_element(Selector::PseudoElement { pseudo_element.value() });
 
@@ -1565,7 +1571,7 @@ void StyleComputer::compute_cascaded_values(StyleProperties& style, DOM::Element
                 element.set_cached_animation_name_animation(animation);
             } else {
                 // The animation hasn't changed, but some properties of the animation may have
-                apply_animation_properties(m_document, style, *element.cached_animation_name_animation());
+                apply_animation_properties(m_document, style, *element.cached_animation_name_animation(), AnimationIsNew::No);
             }
         }
     } else {