diff --git a/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.cpp b/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.cpp
index 812039770e..eb500e4621 100644
--- a/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.cpp
+++ b/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.cpp
@@ -297,4 +297,12 @@ void InlineFormattingContext::generate_line_boxes(LayoutMode layout_mode)
     }
 }
 
+bool InlineFormattingContext::any_floats_intrude_at_y(float y) const
+{
+    auto box_in_root_rect = content_box_rect_in_ancestor_coordinate_space(containing_block(), parent().root(), m_state);
+    float y_in_root = box_in_root_rect.y() + y;
+    auto space = parent().space_used_by_floats(y_in_root);
+    return space.left > 0 || space.right > 0;
+}
+
 }
diff --git a/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.h b/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.h
index a164a96b2a..525f968144 100644
--- a/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.h
+++ b/Userland/Libraries/LibWeb/Layout/InlineFormattingContext.h
@@ -29,6 +29,7 @@ public:
 
     float leftmost_x_offset_at(float y) const;
     float available_space_for_line(float y) const;
+    bool any_floats_intrude_at_y(float y) const;
 
     float effective_containing_block_width() const { return m_effective_containing_block_width; }
 
diff --git a/Userland/Libraries/LibWeb/Layout/LineBuilder.cpp b/Userland/Libraries/LibWeb/Layout/LineBuilder.cpp
index 8167527490..e1176ecc99 100644
--- a/Userland/Libraries/LibWeb/Layout/LineBuilder.cpp
+++ b/Userland/Libraries/LibWeb/Layout/LineBuilder.cpp
@@ -4,6 +4,7 @@
  * SPDX-License-Identifier: BSD-2-Clause
  */
 
+#include <LibWeb/Layout/BlockFormattingContext.h>
 #include <LibWeb/Layout/LineBuilder.h>
 #include <LibWeb/Layout/TextNode.h>
 
@@ -23,11 +24,15 @@ LineBuilder::~LineBuilder()
         update_last_line();
 }
 
-void LineBuilder::break_line()
+void LineBuilder::break_line(Optional<float> next_item_width)
 {
     update_last_line();
-    m_containing_block_state.line_boxes.append(LineBox());
-    begin_new_line(true);
+    do {
+        m_containing_block_state.line_boxes.append(LineBox());
+        begin_new_line(true);
+    } while (next_item_width.has_value()
+        && next_item_width.value() > m_available_width_for_current_line
+        && m_context.any_floats_intrude_at_y(m_current_y));
 }
 
 void LineBuilder::begin_new_line(bool increment_y)
@@ -68,11 +73,18 @@ void LineBuilder::append_text_chunk(TextNode const& text_node, size_t offset_in_
 
 bool LineBuilder::should_break(float next_item_width)
 {
-    auto const& line_boxes = m_containing_block_state.line_boxes;
-    if (line_boxes.is_empty() || line_boxes.last().is_empty())
+    if (!isfinite(m_available_width_for_current_line))
         return false;
-    auto current_line_width = line_boxes.last().width();
-    return (current_line_width + next_item_width) > m_available_width_for_current_line;
+
+    auto const& line_boxes = m_containing_block_state.line_boxes;
+    if (line_boxes.is_empty() || line_boxes.last().is_empty()) {
+        // If we don't have a single line box yet *and* there are no floats intruding
+        // at this Y coordinate, we don't need to break before inserting anything.
+        if (!m_context.any_floats_intrude_at_y(m_current_y))
+            return false;
+    }
+    auto current_line_width = ensure_last_line_box().width();
+    return roundf(current_line_width + next_item_width) > m_available_width_for_current_line;
 }
 
 static float box_baseline(LayoutState const& state, Box const& box)
@@ -255,7 +267,6 @@ void LineBuilder::adjust_last_line_after_inserting_floating_box(Badge<BlockForma
     if (float_ == CSS::Float::Left && !m_containing_block_state.line_boxes.is_empty()) {
         for (auto& fragment : m_containing_block_state.line_boxes.last().fragments())
             fragment.set_offset(fragment.offset().translated(space_used_by_float, 0));
-        m_containing_block_state.line_boxes.last().m_width += space_used_by_float;
     }
 
     m_available_width_for_current_line -= space_used_by_float;
diff --git a/Userland/Libraries/LibWeb/Layout/LineBuilder.h b/Userland/Libraries/LibWeb/Layout/LineBuilder.h
index e666e841c0..b240612d64 100644
--- a/Userland/Libraries/LibWeb/Layout/LineBuilder.h
+++ b/Userland/Libraries/LibWeb/Layout/LineBuilder.h
@@ -18,7 +18,7 @@ public:
     LineBuilder(InlineFormattingContext&, LayoutState&);
     ~LineBuilder();
 
-    void break_line();
+    void break_line(Optional<float> next_item_width = {});
     void append_box(Box const&, float leading_size, float trailing_size, float leading_margin, float trailing_margin);
     void append_text_chunk(TextNode const&, size_t offset_in_node, size_t length_in_node, float leading_size, float trailing_size, float leading_margin, float trailing_margin, float content_width, float content_height);
 
@@ -26,7 +26,7 @@ public:
     bool break_if_needed(float next_item_width)
     {
         if (should_break(next_item_width)) {
-            break_line();
+            break_line(next_item_width);
             return true;
         }
         return false;