diff --git a/data/pref.xml b/data/pref.xml
index 9a4212402..ae8c27c9b 100644
--- a/data/pref.xml
+++ b/data/pref.xml
@@ -46,6 +46,10 @@
       <value id="ACTIVE_LAYER" value="0" />
       <value id="ALL_LAYERS" value="1" />
     </enum>
+    <enum id="PixelConnectivity">
+      <value id="FOUR_CONNECTED" value="0" />
+      <value id="EIGHT_CONNECTED" value="1" />
+    </enum>
     <enum id="EyedropperChannel">
       <value id="COLOR_ALPHA" value="0" />
       <value id="COLOR" value="1" />
@@ -358,6 +362,7 @@
     <section id="floodfill">
       <option id="stop_at_grid" type="StopAtGrid" default="StopAtGrid::NEVER" />
       <option id="refer_to" type="FillReferTo" default="FillReferTo::ACTIVE_LAYER" />
+      <option id="pixel_connectivity" type="PixelConnectivity" default="PixelConnectivity::FOUR_CONNECTED" />
     </section>
   </tool>
 
diff --git a/src/app/script/values.cpp b/src/app/script/values.cpp
index a76836886..012275ef4 100644
--- a/src/app/script/values.cpp
+++ b/src/app/script/values.cpp
@@ -155,6 +155,7 @@ FOR_ENUM(app::gen::HueSaturationMode)
 FOR_ENUM(app::gen::OnionskinType)
 FOR_ENUM(app::gen::PaintingCursorType)
 FOR_ENUM(app::gen::PivotPosition)
+FOR_ENUM(app::gen::PixelConnectivity)
 FOR_ENUM(app::gen::RightClickMode)
 FOR_ENUM(app::gen::SelectionMode)
 FOR_ENUM(app::gen::StopAtGrid)
diff --git a/src/app/tools/point_shapes.h b/src/app/tools/point_shapes.h
index a3a5ecd7c..e45e048f6 100644
--- a/src/app/tools/point_shapes.h
+++ b/src/app/tools/point_shapes.h
@@ -103,6 +103,7 @@ public:
       get_pixel(srcImage, pt.x, pt.y),
       loop->getTolerance(),
       loop->getContiguous(),
+      loop->isPixelConnectivityEightConnected(),
       loop, (AlgoHLine)doInkHline);
   }
 
diff --git a/src/app/tools/tool_loop.h b/src/app/tools/tool_loop.h
index eb6726ac8..9c6a2ea37 100644
--- a/src/app/tools/tool_loop.h
+++ b/src/app/tools/tool_loop.h
@@ -182,6 +182,7 @@ namespace app {
       virtual bool getSnapToGrid() = 0;
       virtual bool getStopAtGrid() = 0; // For floodfill-like tools
       virtual gfx::Rect getGridBounds() = 0;
+      virtual bool isPixelConnectivityEightConnected() = 0;
 
       // Returns true if the figure must be filled when we release the
       // mouse (e.g. a filled rectangle, etc.)
diff --git a/src/app/ui/context_bar.cpp b/src/app/ui/context_bar.cpp
index f76ab8bcc..d365d541f 100644
--- a/src/app/ui/context_bar.cpp
+++ b/src/app/ui/context_bar.cpp
@@ -383,6 +383,16 @@ protected:
     menu.addChild(&activeLayer);
     menu.addChild(&allLayers);
 
+    menu.addChild(new MenuSeparator);
+    menu.addChild(new Label("Pixel Connectivity:"));
+
+    HBox box;
+    ButtonSet buttonset(2);
+    buttonset.addItem("4-Connected");
+    buttonset.addItem("8-connected");
+    box.addChild(&buttonset);
+    menu.addChild(&box);
+
     stopAtGrid.setSelected(
       toolPref.floodfill.stopAtGrid() == app::gen::StopAtGrid::IF_VISIBLE);
     activeLayer.setSelected(
@@ -390,6 +400,15 @@ protected:
     allLayers.setSelected(
       toolPref.floodfill.referTo() == app::gen::FillReferTo::ALL_LAYERS);
 
+    int index = 0;
+
+    switch (toolPref.floodfill.pixelConnectivity()) {
+      case app::gen::PixelConnectivity::FOUR_CONNECTED: index = 0; break;
+      case app::gen::PixelConnectivity::EIGHT_CONNECTED: index = 1; break;
+    }
+
+    buttonset.setSelectedItem(index);
+
     stopAtGrid.Click.connect(
       [&]{
         toolPref.floodfill.stopAtGrid(
@@ -405,6 +424,18 @@ protected:
         toolPref.floodfill.referTo(app::gen::FillReferTo::ALL_LAYERS);
       });
 
+    buttonset.ItemChange.connect(
+      [&buttonset, &toolPref](ButtonSet::Item* item){
+        switch (buttonset.selectedItem()) {
+          case 0:
+            toolPref.floodfill.pixelConnectivity(app::gen::PixelConnectivity::FOUR_CONNECTED);
+            break;
+          case 1:
+            toolPref.floodfill.pixelConnectivity(app::gen::PixelConnectivity::EIGHT_CONNECTED);
+            break;
+        }
+      });
+
     menu.showPopup(gfx::Point(bounds.x, bounds.y+bounds.h));
     deselectItems();
   }
diff --git a/src/app/ui/editor/tool_loop_impl.cpp b/src/app/ui/editor/tool_loop_impl.cpp
index cb8169b2f..0f4f39a0f 100644
--- a/src/app/ui/editor/tool_loop_impl.cpp
+++ b/src/app/ui/editor/tool_loop_impl.cpp
@@ -246,6 +246,12 @@ public:
     }
     return false;
   }
+
+  bool isPixelConnectivityEightConnected() override {
+    return (m_toolPref.floodfill.pixelConnectivity()
+            == app::gen::PixelConnectivity::EIGHT_CONNECTED);
+  }
+
   gfx::Rect getGridBounds() override { return m_docPref.grid.bounds(); }
   gfx::Point getCelOrigin() override { return m_celOrigin; }
   void setSpeed(const gfx::Point& speed) override { m_speed = speed; }
diff --git a/src/doc/algorithm/floodfill.cpp b/src/doc/algorithm/floodfill.cpp
index 87c07b63c..c3116e0f2 100644
--- a/src/doc/algorithm/floodfill.cpp
+++ b/src/doc/algorithm/floodfill.cpp
@@ -346,6 +346,7 @@ void floodfill(const Image* image,
                const doc::color_t src_color,
                const int tolerance,
                const bool contiguous,
+               const bool isEightConnected,
                void* data,
                AlgoHLine proc)
 {
@@ -398,8 +399,39 @@ void floodfill(const Image* image,
       // Check below the segment?
       if (p->flags & FLOOD_TODO_BELOW) {
         p->flags &= ~FLOOD_TODO_BELOW;
+
+        if (isEightConnected) {
+          if (p->lpos+1 < bounds.x2() &&
+              check_flood_line(image, mask, p->y+1, p->lpos+1, p->rpos, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+            p = FLOOD_LINE(c);
+          }
+
+          if (p->lpos-1 >= 0 &&
+              check_flood_line(image, mask, p->y+1, p->lpos-1, p->rpos, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+            p = FLOOD_LINE(c);
+          }
+
+          if (p->rpos+1 < bounds.x2() &&
+              check_flood_line(image, mask, p->y+1, p->lpos, p->rpos+1, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+            p = FLOOD_LINE(c);
+          }
+
+          if (p->rpos-1 >= 0 &&
+              check_flood_line(image, mask, p->y+1, p->lpos, p->rpos-1, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+            p = FLOOD_LINE(c);
+          }
+        }
+
         if (check_flood_line(image, mask, p->y+1, p->lpos, p->rpos, bounds,
-            src_color, tolerance, data, proc)) {
+                             src_color, tolerance, data, proc)) {
           done = false;
           p = FLOOD_LINE(c);
         }
@@ -408,6 +440,31 @@ void floodfill(const Image* image,
       // Check above the segment?
       if (p->flags & FLOOD_TODO_ABOVE) {
         p->flags &= ~FLOOD_TODO_ABOVE;
+
+        if (isEightConnected) {
+          if (p->lpos+1 < bounds.x2() &&
+              check_flood_line(image, mask, p->y-1, p->lpos+1, p->rpos, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+          }
+          if (p->lpos-1 >= 0 &&
+              check_flood_line(image, mask, p->y-1, p->lpos-1, p->rpos, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+          }
+
+          if (p->rpos+1 < bounds.x2() &&
+              check_flood_line(image, mask, p->y-1, p->lpos, p->rpos+1, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+          }
+          if (p->rpos-1 >= 0 &&
+              check_flood_line(image, mask, p->y-1, p->lpos, p->rpos-1, bounds,
+                               src_color, tolerance, data, proc)) {
+            done = false;
+          }
+        }
+
         if (check_flood_line(image, mask, p->y-1, p->lpos, p->rpos, bounds,
                              src_color, tolerance, data, proc)) {
           done = false;
diff --git a/src/doc/algorithm/floodfill.h b/src/doc/algorithm/floodfill.h
index 5bed5f767..e4fd37a08 100644
--- a/src/doc/algorithm/floodfill.h
+++ b/src/doc/algorithm/floodfill.h
@@ -26,6 +26,7 @@ namespace doc {
                    const doc::color_t srcColor,
                    const int tolerance,
                    const bool contiguous,
+                   const bool isEightConnected,
                    void* data,
                    AlgoHLine proc);