diff --git a/Libraries/LibWeb/Layout/LineBuilder.cpp b/Libraries/LibWeb/Layout/LineBuilder.cpp
index 60d53e4d98b..89f16e12bf3 100644
--- a/Libraries/LibWeb/Layout/LineBuilder.cpp
+++ b/Libraries/LibWeb/Layout/LineBuilder.cpp
@@ -129,23 +129,44 @@ CSSPixels LineBuilder::y_for_float_to_be_inserted_here(Box const& box)
 
     // Then, look for the next Y position where we can fit the new float.
     auto box_in_root_rect = m_context.parent().content_box_rect_in_ancestor_coordinate_space(box_state, m_context.parent().root());
-    m_context.parent().for_each_floating_box([&](auto const& float_box) {
-        auto candidate_block_offset_in_root = box_in_root_rect.y() + candidate_block_offset;
-        if (float_box.margin_box_rect_in_root_coordinate_space.bottom() < candidate_block_offset_in_root)
+
+    HashMap<CSSPixels, AvailableSize> available_space_cache;
+    for (;;) {
+        Optional<CSSPixels> highest_intersection_bottom;
+
+        auto candidate_block_top_in_root = box_in_root_rect.y() + candidate_block_offset;
+        auto candidate_block_bottom_in_root = candidate_block_top_in_root + height;
+
+        m_context.parent().for_each_floating_box([&](auto const& float_box) {
+            auto float_box_top = float_box.margin_box_rect_in_root_coordinate_space.top();
+            auto float_box_bottom = float_box.margin_box_rect_in_root_coordinate_space.bottom();
+            if (float_box_bottom <= candidate_block_top_in_root)
+                return IterationDecision::Continue;
+
+            auto intersection_test = [&](auto y_coordinate, auto top, auto bottom) {
+                if (y_coordinate < top || y_coordinate > bottom)
+                    return;
+                auto available_space = available_space_cache.ensure(y_coordinate, [&]() {
+                    return m_context.available_space_for_line(y_coordinate);
+                });
+                if (width > available_space) {
+                    auto bottom_relative = float_box_bottom - box_in_root_rect.y();
+                    highest_intersection_bottom = min(highest_intersection_bottom.value_or(bottom_relative), bottom_relative);
+                }
+            };
+
+            intersection_test(float_box_top, candidate_block_top_in_root, candidate_block_bottom_in_root);
+            intersection_test(float_box_bottom, candidate_block_top_in_root, candidate_block_bottom_in_root);
+            intersection_test(candidate_block_top_in_root, float_box_top, float_box_bottom);
+            intersection_test(candidate_block_bottom_in_root, float_box_top, float_box_bottom);
+
             return IterationDecision::Continue;
-        auto space_at_y_top = m_context.available_space_for_line(candidate_block_offset);
-        auto space_at_y_bottom = m_context.available_space_for_line(candidate_block_offset + height);
-        if (width > space_at_y_top || width > space_at_y_bottom) {
-            if (!m_context.any_floats_intrude_at_block_offset(candidate_block_offset) && !m_context.any_floats_intrude_at_block_offset(candidate_block_offset + height)) {
-                return IterationDecision::Break;
-            }
-        } else {
-            return IterationDecision::Break;
-        }
-        // candidate_block_offset needs to stay relative to the current box
-        candidate_block_offset = float_box.margin_box_rect_in_root_coordinate_space.bottom() - box_in_root_rect.y();
-        return IterationDecision::Continue;
-    });
+        });
+        if (!highest_intersection_bottom.has_value() || highest_intersection_bottom.value() == candidate_block_offset)
+            break;
+        candidate_block_offset = highest_intersection_bottom.value();
+    }
+
     return candidate_block_offset;
 }
 
diff --git a/Tests/LibWeb/Layout/expected/block-and-inline/float-initial-available-space-vs-height.txt b/Tests/LibWeb/Layout/expected/block-and-inline/float-initial-available-space-vs-height.txt
new file mode 100644
index 00000000000..4f66fd80532
--- /dev/null
+++ b/Tests/LibWeb/Layout/expected/block-and-inline/float-initial-available-space-vs-height.txt
@@ -0,0 +1,25 @@
+Viewport <#document> at (0,0) content-size 800x600 children: not-inline
+  BlockContainer <html> at (0,0) content-size 800x413 [BFC] children: not-inline
+    BlockContainer <body> at (8,8) content-size 784x5 children: not-inline
+      BlockContainer <div.a> at (8,8) content-size 100x5 children: inline
+        frag 0 from TextNode start: 1, length: 1, rect: [8,8 4.328125x5] baseline: 4
+            "H"
+        TextNode <#text>
+        BlockContainer <div.b.l> at (8,13) content-size 100x100 floating [BFC] children: not-inline
+        TextNode <#text>
+        BlockContainer <div.c.l> at (8,113) content-size 30x300 floating [BFC] children: not-inline
+        TextNode <#text>
+        BlockContainer <div.c.r> at (78,113) content-size 30x300 floating [BFC] children: not-inline
+        TextNode <#text>
+      BlockContainer <(anonymous)> at (8,13) content-size 784x0 children: inline
+        TextNode <#text>
+
+ViewportPaintable (Viewport<#document>) [0,0 800x600]
+  PaintableWithLines (BlockContainer<HTML>) [0,0 800x413]
+    PaintableWithLines (BlockContainer<BODY>) [8,8 784x5]
+      PaintableWithLines (BlockContainer<DIV>.a) [8,8 100x5]
+        TextPaintable (TextNode<#text>)
+        PaintableWithLines (BlockContainer<DIV>.b.l) [8,13 100x100]
+        PaintableWithLines (BlockContainer<DIV>.c.l) [8,113 30x300]
+        PaintableWithLines (BlockContainer<DIV>.c.r) [78,113 30x300]
+      PaintableWithLines (BlockContainer(anonymous)) [8,13 784x0]
diff --git a/Tests/LibWeb/Layout/expected/block-and-inline/float-vertical-clearance-ignores-opposite-side.txt b/Tests/LibWeb/Layout/expected/block-and-inline/float-vertical-clearance-ignores-opposite-side.txt
new file mode 100644
index 00000000000..36b6ae487f2
--- /dev/null
+++ b/Tests/LibWeb/Layout/expected/block-and-inline/float-vertical-clearance-ignores-opposite-side.txt
@@ -0,0 +1,22 @@
+Viewport <#document> at (0,0) content-size 800x600 children: not-inline
+  BlockContainer <html> at (0,0) content-size 800x216 [BFC] children: not-inline
+    BlockContainer <body> at (8,8) content-size 784x200 children: not-inline
+      BlockContainer <div.a> at (8,8) content-size 500x200 children: inline
+        TextNode <#text>
+        BlockContainer <div.b> at (8,8) content-size 200x150 floating [BFC] children: not-inline
+        TextNode <#text>
+        BlockContainer <div.c> at (308,8) content-size 200x100 floating [BFC] children: not-inline
+        TextNode <#text>
+        BlockContainer <div.d> at (308,108) content-size 200x100 floating [BFC] children: not-inline
+        TextNode <#text>
+      BlockContainer <(anonymous)> at (8,208) content-size 784x0 children: inline
+        TextNode <#text>
+
+ViewportPaintable (Viewport<#document>) [0,0 800x600]
+  PaintableWithLines (BlockContainer<HTML>) [0,0 800x216]
+    PaintableWithLines (BlockContainer<BODY>) [8,8 784x200]
+      PaintableWithLines (BlockContainer<DIV>.a) [8,8 500x200]
+        PaintableWithLines (BlockContainer<DIV>.b) [8,8 200x150]
+        PaintableWithLines (BlockContainer<DIV>.c) [308,8 200x100]
+        PaintableWithLines (BlockContainer<DIV>.d) [308,108 200x100]
+      PaintableWithLines (BlockContainer(anonymous)) [8,208 784x0]
diff --git a/Tests/LibWeb/Layout/input/block-and-inline/float-initial-available-space-vs-height.html b/Tests/LibWeb/Layout/input/block-and-inline/float-initial-available-space-vs-height.html
new file mode 100644
index 00000000000..2d3433d52db
--- /dev/null
+++ b/Tests/LibWeb/Layout/input/block-and-inline/float-initial-available-space-vs-height.html
@@ -0,0 +1,29 @@
+<!DOCTYPE html>
+<style>
+.a {
+    font-size: 5px;
+    width: 100px;
+}
+.b {
+    background-color: blue;
+    height: 100px;
+    width: 100px;
+}
+.c {
+    background-color: yellow;
+    height: 300px;
+    width: 30px;
+}
+.l {
+    float: left;
+}
+.r {
+    float: right;
+}
+</style>
+<div class="a">
+    H
+    <div class="b l"></div>
+    <div class="c l"></div>
+    <div class="c r"></div>
+</div>
diff --git a/Tests/LibWeb/Layout/input/block-and-inline/float-vertical-clearance-ignores-opposite-side.html b/Tests/LibWeb/Layout/input/block-and-inline/float-vertical-clearance-ignores-opposite-side.html
new file mode 100644
index 00000000000..4760e5c46fe
--- /dev/null
+++ b/Tests/LibWeb/Layout/input/block-and-inline/float-vertical-clearance-ignores-opposite-side.html
@@ -0,0 +1,30 @@
+<!DOCTYPE html>
+<style>
+.a {
+    height: 200px;
+    width: 500px;
+}
+.b {
+    float: left;
+    background: red;
+    height: 150px;
+    width: 200px;
+}
+.c {
+    float: right;
+    background: green;
+    height: 100px;
+    width: 200px;
+}
+.d {
+    float: right;
+    background: blue;
+    height: 100px;
+    width: 200px;
+}
+</style>
+<div class="a">
+    <div class="b"></div>
+    <div class="c"></div>
+    <div class="d"></div>
+</div>