diff --git a/src/display/draw_layer.js b/src/display/draw_layer.js
index 4ef018a676dae2..3d4fa72d623582 100644
--- a/src/display/draw_layer.js
+++ b/src/display/draw_layer.js
@@ -135,9 +135,33 @@ class DrawLayer {
     path.setAttribute("d", outlines.toSVGPath());
     path.setAttribute("vector-effect", "non-scaling-stroke");
 
+    let maskId;
+    if (outlines.free) {
+      root.classList.add("free");
+      const mask = DrawLayer._svgFactory.createElement("mask");
+      defs.append(mask);
+      maskId = `mask_p${this.pageIndex}_${id}`;
+      mask.setAttribute("id", maskId);
+      mask.setAttribute("maskUnits", "objectBoundingBox");
+      const rect = DrawLayer._svgFactory.createElement("rect");
+      mask.append(rect);
+      rect.setAttribute("width", "1");
+      rect.setAttribute("height", "1");
+      rect.setAttribute("fill", "white");
+      const use = DrawLayer._svgFactory.createElement("use");
+      mask.append(use);
+      use.setAttribute("href", `#${pathId}`);
+      use.setAttribute("stroke", "none");
+      use.setAttribute("fill", "black");
+      use.setAttribute("fill-rule", "nonzero");
+    }
+
     const use1 = DrawLayer._svgFactory.createElement("use");
     root.append(use1);
     use1.setAttribute("href", `#${pathId}`);
+    if (maskId) {
+      use1.setAttribute("mask", `url(#${maskId})`);
+    }
     const use2 = use1.cloneNode();
     root.append(use2);
     use1.classList.add("mainOutline");
diff --git a/web/draw_layer_builder.css b/web/draw_layer_builder.css
index b5bffec78c5739..1cfe86f91efb02 100644
--- a/web/draw_layer_builder.css
+++ b/web/draw_layer_builder.css
@@ -56,22 +56,52 @@
       fill-rule: evenodd;
       fill: none;
 
-      &.hovered {
-        stroke: var(--hover-outline-color);
-        stroke-width: var(--outline-width);
+      &:not(.free) {
+        &.hovered:not(.selected) {
+          stroke: var(--hover-outline-color);
+          stroke-width: var(--outline-width);
+        }
+
+        &.selected {
+          .mainOutline {
+            stroke: var(--outline-around-color);
+            stroke-width: calc(
+              var(--outline-width) + 2 * var(--outline-around-width)
+            );
+          }
+
+          .secondaryOutline {
+            stroke: var(--outline-color);
+            stroke-width: var(--outline-width);
+          }
+        }
       }
 
-      &.selected {
-        .mainOutline {
-          stroke: var(--outline-around-color);
-          stroke-width: calc(
-            var(--outline-width) + 2 * var(--outline-around-width)
-          );
+      &.free {
+        /*
+          When drawing the outline we use a mask in order to remove the parts
+          that are inside the shape. Unfortunately, this removes the part of the
+          outline that is inside the shape. To "fix" this we draw the outline
+          we increase the width to have what we want to be visible outside the
+          shape. This is not a perfect solution, but it works well enough.
+        */
+        &.hovered:not(.selected) {
+          stroke: var(--hover-outline-color);
+          stroke-width: calc(2 * var(--outline-width));
         }
 
-        .secondaryOutline {
-          stroke: var(--outline-color);
-          stroke-width: var(--outline-width);
+        &.selected {
+          .mainOutline {
+            stroke: var(--outline-around-color);
+            stroke-width: calc(
+              2 * (2 * var(--outline-width) + var(--outline-around-width))
+            );
+          }
+
+          .secondaryOutline {
+            stroke: var(--outline-color);
+            stroke-width: calc(2 * var(--outline-width));
+          }
         }
       }
     }