diff --git a/build/configure/src/web.rs b/build/configure/src/web.rs
index f02bd7a47..4d7b744a7 100644
--- a/build/configure/src/web.rs
+++ b/build/configure/src/web.rs
@@ -292,7 +292,7 @@ fn build_and_check_reviewer(build: &mut Build) -> Result<()> {
 fn check_web(build: &mut Build) -> Result<()> {
     let dprint_files = inputs![glob![
         "**/*.{ts,mjs,js,md,json,toml,svelte,scss}",
-        "{target,ts/.svelte-kit}/**"
+        "{target,ts/.svelte-kit,node_modules}/**"
     ]];
     build.add_action(
         "check:format:dprint",
diff --git a/ts/routes/image-occlusion/Toolbar.svelte b/ts/routes/image-occlusion/Toolbar.svelte
index 2e00f64b9..8941ab39a 100644
--- a/ts/routes/image-occlusion/Toolbar.svelte
+++ b/ts/routes/image-occlusion/Toolbar.svelte
@@ -471,6 +471,10 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
         font-size: 16px !important;
     }
 
+    :global(.top-tool-icon-button:active) {
+        background: var(--highlight-bg) !important;
+    }
+
     .dropdown-content {
         display: none;
         position: absolute;
@@ -480,7 +484,7 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
     }
 
     .show {
-        display: flex;
+        display: table;
     }
 
     ::-webkit-scrollbar {
diff --git a/ts/routes/image-occlusion/shapes/to-cloze.ts b/ts/routes/image-occlusion/shapes/to-cloze.ts
index ce4dfacbb..521666f60 100644
--- a/ts/routes/image-occlusion/shapes/to-cloze.ts
+++ b/ts/routes/image-occlusion/shapes/to-cloze.ts
@@ -19,23 +19,71 @@ export function exportShapesToClozeDeletions(occludeInactive: boolean): {
     const shapes = baseShapesFromFabric();
 
     let clozes = "";
-    let index = 0;
-    shapes.forEach((shapeOrShapes) => {
-        // shapes with width or height less than 5 are not valid
-        if (shapeOrShapes === null) {
-            return;
-        }
-        // if shape is Rect and fill is transparent, skip it
-        if (shapeOrShapes instanceof Rectangle && shapeOrShapes.fill === "transparent") {
-            return;
-        }
-        clozes += shapeOrShapesToCloze(shapeOrShapes, index, occludeInactive);
-        if (!(shapeOrShapes instanceof Text)) {
-            index++;
+    let noteCount = 0;
+
+    // take out all ordinal values from shapes
+    const ordinalList = shapes.map((shape) => {
+        if (Array.isArray(shape)) {
+            return shape[0].ordinal;
+        } else {
+            return shape.ordinal;
         }
     });
 
-    return { clozes, noteCount: index };
+    const filterOrdinalList: number[] = ordinalList.flatMap(v => typeof v === "number" ? [v] : []);
+    const maxOrdinal = Math.max(...filterOrdinalList, 0);
+
+    const missingOrdinals: number[] = [];
+    for (let i = 1; i <= maxOrdinal; i++) {
+        if (!ordinalList.includes(i)) {
+            missingOrdinals.push(i);
+        }
+    }
+
+    let nextOrdinal = maxOrdinal + 1;
+
+    shapes.map((shapeOrShapes) => {
+        if (shapeOrShapes === null) {
+            return;
+        }
+
+        // Maintain existing ordinal in editing mode
+        let ordinal: number | undefined;
+        if (Array.isArray(shapeOrShapes)) {
+            ordinal = shapeOrShapes[0].ordinal;
+        } else {
+            ordinal = shapeOrShapes.ordinal;
+        }
+
+        if (ordinal === undefined) {
+            // if ordinal is undefined, assign a missing ordinal if available
+            if (shapeOrShapes instanceof Text) {
+                ordinal = 0;
+            } else if (missingOrdinals.length > 0) {
+                ordinal = missingOrdinals.shift() as number;
+            } else {
+                ordinal = nextOrdinal;
+                nextOrdinal++;
+            }
+
+            if (Array.isArray(shapeOrShapes)) {
+                shapeOrShapes.forEach((shape) => (shape.ordinal = ordinal));
+            } else {
+                shapeOrShapes.ordinal = ordinal;
+            }
+        }
+
+        clozes += shapeOrShapesToCloze(
+            shapeOrShapes,
+            ordinal,
+            occludeInactive,
+        );
+
+        if (!(shapeOrShapes instanceof Text)) {
+            noteCount++;
+        }
+    });
+    return { clozes, noteCount };
 }
 
 /** Gather all Fabric shapes, and convert them into BaseShapes or
@@ -50,6 +98,7 @@ export function baseShapesFromFabric(): ShapeOrShapes[] {
         : null;
     const objects = canvas.getObjects() as fabric.Object[];
     const boundingBox = getBoundingBox();
+    // filter transparent rectangles
     return objects
         .map((object) => {
             // If the object is in the active selection containing multiple objects,
@@ -57,7 +106,9 @@ export function baseShapesFromFabric(): ShapeOrShapes[] {
             const parent = selectionContainingMultipleObjects?.contains(object)
                 ? selectionContainingMultipleObjects
                 : undefined;
-            if (object.width! < 5 || object.height! < 5) {
+            // shapes with width or height less than 5 are not valid
+            // if shape is Rect and fill is transparent, skip it
+            if (object.width! < 5 || object.height! < 5 || object.fill == "transparent") {
                 return null;
             }
             return fabricObjectToBaseShapeOrShapes(
@@ -131,7 +182,7 @@ function fabricObjectToBaseShapeOrShapes(
  {{c1::image-occlusion:rect:top=.1:left=.23:width=.4:height=.5}} */
 function shapeOrShapesToCloze(
     shapeOrShapes: ShapeOrShapes,
-    index: number,
+    ordinal: number,
     occludeInactive: boolean,
 ): string {
     let text = "";
@@ -143,7 +194,7 @@ function shapeOrShapesToCloze(
     let type: string;
     if (Array.isArray(shapeOrShapes)) {
         return shapeOrShapes
-            .map((shape) => shapeOrShapesToCloze(shape, index, occludeInactive))
+            .map((shape) => shapeOrShapesToCloze(shape, ordinal, occludeInactive))
             .join("");
     } else if (shapeOrShapes instanceof Rectangle) {
         type = "rect";
@@ -164,16 +215,6 @@ function shapeOrShapesToCloze(
         addKeyValue("oi", "1");
     }
 
-    // Maintain existing ordinal in editing mode
-    let ordinal = shapeOrShapes.ordinal;
-    if (ordinal === undefined) {
-        if (type === "text") {
-            ordinal = 0;
-        } else {
-            ordinal = index + 1;
-        }
-        shapeOrShapes.ordinal = ordinal;
-    }
     text = `{{c${ordinal}::image-occlusion:${type}${text}}}<br>`;
 
     return text;
diff --git a/ts/routes/image-occlusion/tools/lib.ts b/ts/routes/image-occlusion/tools/lib.ts
index 19543c26f..953ac290e 100644
--- a/ts/routes/image-occlusion/tools/lib.ts
+++ b/ts/routes/image-occlusion/tools/lib.ts
@@ -63,12 +63,20 @@ export const groupShapes = (canvas: fabric.Canvas): void => {
 
     const activeObject = canvas.getActiveObject() as fabric.ActiveSelection;
     const items = activeObject.getObjects();
+
+    // @ts-expect-error not defined
+    let minOrdinal: number | undefined = Math.min(...items.map((item) => item.ordinal));
+    minOrdinal = Number.isNaN(minOrdinal) ? undefined : minOrdinal;
+
     items.forEach((item) => {
-        item.set({ opacity: 1 });
+        // @ts-expect-error not defined
+        item.set({ opacity: 1, ordinal: minOrdinal });
     });
+
     activeObject.toGroup().set({
         opacity: get(opacityStateStore) ? 0.4 : 1,
     });
+
     redraw(canvas);
 };
 
@@ -84,13 +92,17 @@ export const unGroupShapes = (canvas: fabric.Canvas): void => {
     group._restoreObjectsState();
     // @ts-expect-error not defined
     group.destroyed = true;
-    canvas.remove(group);
 
     items.forEach((item) => {
-        item.set({ opacity: get(opacityStateStore) ? 0.4 : 1 });
+        item.set({
+            opacity: get(opacityStateStore) ? 0.4 : 1,
+            // @ts-expect-error not defined
+            ordinal: undefined,
+        });
         canvas.add(item);
     });
 
+    canvas.remove(group);
     redraw(canvas);
 };
 
@@ -283,9 +295,13 @@ export const makeShapeRemainInCanvas = (canvas: fabric.Canvas, boundingBox: fabr
 
 export const selectAllShapes = (canvas: fabric.Canvas) => {
     canvas.discardActiveObject();
-    const sel = new fabric.ActiveSelection(canvas.getObjects(), {
-        canvas: canvas,
-    });
+    // filter out the transparent bounding box from the selection
+    const sel = new fabric.ActiveSelection(
+        canvas.getObjects().filter((obj) => obj.fill !== "transparent"),
+        {
+            canvas: canvas,
+        },
+    );
     canvas.setActiveObject(sel);
     redraw(canvas);
 };
diff --git a/ts/routes/image-occlusion/tools/tool-undo-redo.ts b/ts/routes/image-occlusion/tools/tool-undo-redo.ts
index 0a8b91108..aa073dfe4 100644
--- a/ts/routes/image-occlusion/tools/tool-undo-redo.ts
+++ b/ts/routes/image-occlusion/tools/tool-undo-redo.ts
@@ -2,7 +2,7 @@
 // License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
 
 import * as tr from "@generated/ftl";
-import { type fabric } from "fabric";
+import { fabric } from "fabric";
 import { writable } from "svelte/store";
 
 import { mdiRedo, mdiUndo } from "../icons";
@@ -87,6 +87,12 @@ class UndoStack {
             emitChangeSignal();
             this.locked = false;
         });
+        // make bounding box unselectable
+        this.canvas?.forEachObject((obj) => {
+            if (obj instanceof fabric.Rect && obj.fill === "transparent") {
+                obj.selectable = false;
+            }
+        });
     }
 
     onObjectAdded(id: string): void {