diff --git a/gradesa/src/app/api/exercises/dragdrop/[dnd_id]/route.js b/gradesa/src/app/api/exercises/dragdrop/[dnd_id]/route.js
index 17627c6..23e6179 100644
--- a/gradesa/src/app/api/exercises/dragdrop/[dnd_id]/route.js
+++ b/gradesa/src/app/api/exercises/dragdrop/[dnd_id]/route.js
@@ -37,17 +37,18 @@ export const GET = withAuth(async (request, { params }) => {
       [dnd_id]
     );
 
-    // Fetch words with their correct categories
+    // Fetch words with all of their correct categories (a word can belong to more than one group)
     const words = await DB.pool(
       `
       SELECT 
         dw.id,
         dw.word as name,
-        dc.category as type
+        ARRAY_AGG(DISTINCT dc.category) as types
       FROM draggable_words dw
       JOIN word_category_mappings wcm ON dw.id = wcm.word_id
       JOIN dnd_categories dc ON wcm.category_id = dc.id
       WHERE wcm.exercise_id = $1
+      GROUP BY dw.id, dw.word
     `,
       [dnd_id]
     );
diff --git a/gradesa/src/app/grammar/exercises/fillinthegap/[exercise_id]/page.js b/gradesa/src/app/grammar/exercises/fillinthegap/[exercise_id]/page.js
index 212b3ca..ab22240 100644
--- a/gradesa/src/app/grammar/exercises/fillinthegap/[exercise_id]/page.js
+++ b/gradesa/src/app/grammar/exercises/fillinthegap/[exercise_id]/page.js
@@ -40,6 +40,80 @@ function tokenizeRaw(raw) {
   };
 }
 
+// Same block set as normalizeEditorText's BLOCK_BREAK_TAGS (minus "br", handled separately below).
+const BLOCK_ANCESTOR_TAGS = new Set([
+  "p",
+  "div",
+  "li",
+  "ul",
+  "ol",
+  "h1",
+  "h2",
+  "h3",
+  "h4",
+  "h5",
+  "h6",
+  "tr",
+  "table",
+]);
+
+function getBlockAncestor(node, root) {
+  let el = node.parentNode;
+  while (el && el !== root) {
+    if (
+      el.nodeType === 1 &&
+      BLOCK_ANCESTOR_TAGS.has(el.tagName.toLowerCase())
+    ) {
+      return el;
+    }
+    el = el.parentNode;
+  }
+  return root;
+}
+
+// Groups text nodes into runs of contiguous prose: only block tags/<br> start a new
+// run, so a word split across inline tags (e.g. <strong>) still tokenizes as one word.
+function groupTextNodesIntoRuns(doc, root, NodeFilter) {
+  const walker = doc.createTreeWalker(
+    root,
+    NodeFilter.SHOW_TEXT | NodeFilter.SHOW_ELEMENT,
+    {
+      acceptNode(node) {
+        if (node.nodeType === 3) return NodeFilter.FILTER_ACCEPT;
+        if (node.nodeType === 1 && node.tagName === "BR")
+          return NodeFilter.FILTER_ACCEPT;
+        return NodeFilter.FILTER_SKIP;
+      },
+    }
+  );
+
+  const runs = [];
+  let currentRun = [];
+  let currentBlock = null;
+  let node;
+
+  while ((node = walker.nextNode())) {
+    if (node.nodeType === 1) {
+      if (currentRun.length) runs.push(currentRun);
+      currentRun = [];
+      currentBlock = null;
+      continue;
+    }
+
+    const block = getBlockAncestor(node, root);
+    if (currentRun.length && block === currentBlock) {
+      currentRun.push(node);
+    } else {
+      if (currentRun.length) runs.push(currentRun);
+      currentRun = [node];
+      currentBlock = block;
+    }
+  }
+  if (currentRun.length) runs.push(currentRun);
+
+  return runs;
+}
+
 function buildHtmlWithGapPlaceholders(sourceHtml, gapsByTokenIndex) {
   if (!sourceHtml || typeof window === "undefined") {
     return "";
@@ -55,44 +129,61 @@ function buildHtmlWithGapPlaceholders(sourceHtml, gapsByTokenIndex) {
     return sourceHtml;
   }
 
-  const walker = doc.createTreeWalker(root, window.NodeFilter.SHOW_TEXT);
-  const textNodes = [];
-  let current;
-
-  while ((current = walker.nextNode())) {
-    textNodes.push(current);
-  }
-
+  const runs = groupTextNodesIntoRuns(doc, root, window.NodeFilter);
   let tokenIndex = 0;
 
-  for (const textNode of textNodes) {
-    const rawText = textNode.nodeValue || "";
-    const chunks = rawText.match(/\s+|[^\s]+/g) || [];
-    const fragment = doc.createDocumentFragment();
+  for (const nodes of runs) {
+    // Concatenate the run's text so a word split across inline tags is one token.
+    const boundaries = [];
+    let offset = 0;
+    for (const node of nodes) {
+      const length = (node.nodeValue || "").length;
+      boundaries.push({ node, start: offset, end: offset + length });
+      offset += length;
+    }
+    const runText = nodes.map((node) => node.nodeValue || "").join("");
+    const chunks = runText.match(/\s+|[^\s]+/g) || [];
 
+    const fragments = new Map(
+      nodes.map((node) => [node, doc.createDocumentFragment()])
+    );
+    const appendAt = (absOffset, contentNode) => {
+      const boundary =
+        boundaries.find((b) => absOffset >= b.start && absOffset < b.end) ||
+        boundaries[boundaries.length - 1];
+      fragments.get(boundary.node).appendChild(contentNode);
+    };
+
+    let cursor = 0;
     for (const chunk of chunks) {
+      const chunkStart = cursor;
+      cursor += chunk.length;
+
       if (/^\s+$/.test(chunk)) {
-        fragment.appendChild(doc.createTextNode(chunk));
+        appendAt(chunkStart, doc.createTextNode(chunk));
         continue;
       }
 
       const tokenParts = tokenizeRaw(chunk);
       const gap = gapsByTokenIndex.get(tokenIndex);
+      let partOffset = chunkStart;
 
       if (gap && tokenParts.word) {
         if (tokenParts.prefix) {
-          fragment.appendChild(doc.createTextNode(tokenParts.prefix));
+          appendAt(partOffset, doc.createTextNode(tokenParts.prefix));
+          partOffset += tokenParts.prefix.length;
         }
 
         const gapNode = doc.createElement("fitg-gap");
         gapNode.setAttribute("data-gap-id", String(gap.id));
-        fragment.appendChild(gapNode);
+        appendAt(partOffset, gapNode);
+        partOffset += tokenParts.word.length;
 
         if (tokenParts.suffix) {
-          fragment.appendChild(doc.createTextNode(tokenParts.suffix));
+          appendAt(partOffset, doc.createTextNode(tokenParts.suffix));
         }
       } else {
-        fragment.appendChild(doc.createTextNode(chunk));
+        appendAt(chunkStart, doc.createTextNode(chunk));
       }
 
       if (tokenParts.word) {
@@ -100,7 +191,9 @@ function buildHtmlWithGapPlaceholders(sourceHtml, gapsByTokenIndex) {
       }
     }
 
-    textNode.parentNode?.replaceChild(fragment, textNode);
+    for (const node of nodes) {
+      node.parentNode?.replaceChild(fragments.get(node), node);
+    }
   }
 
   return root.innerHTML;
diff --git a/gradesa/src/components/ui/dragdrop/area.js b/gradesa/src/components/ui/dragdrop/area.js
index e0facf2..2029e73 100644
--- a/gradesa/src/components/ui/dragdrop/area.js
+++ b/gradesa/src/components/ui/dragdrop/area.js
@@ -82,7 +82,9 @@ const Area = ({ exerciseID }) => {
     const allBoxesPlaced = totalDroppedItems === allWords.length;
 
     const allItemsCorrect = updatedDustbins.every((dustbin) =>
-      dustbin.droppedItems.every((item) => item.type === dustbin.accepts[0])
+      dustbin.droppedItems.every((item) =>
+        item.types.includes(dustbin.accepts[0])
+      )
     );
 
     return allBoxesPlaced && allItemsCorrect;
@@ -90,7 +92,7 @@ const Area = ({ exerciseID }) => {
 
   const handleDrop = useCallback(
     (index, item) => {
-      const { name, type } = item;
+      const { name, types } = item;
 
       if (droppedBoxNames.includes(name)) return;
 
@@ -98,7 +100,7 @@ const Area = ({ exerciseID }) => {
         if (binIndex === index) {
           return {
             ...bin,
-            droppedItems: [...bin.droppedItems, { name, type }],
+            droppedItems: [...bin.droppedItems, { name, types }],
           };
         }
         return bin;
@@ -150,7 +152,7 @@ const Area = ({ exerciseID }) => {
   if (isLoading) return <div>Lädt...</div>;
   if (error) return <div>Fehler: {error}</div>;
 
-  const allAcceptedTypes = [...new Set(allWords.map((word) => word.type))];
+  const allAcceptedTypes = [...new Set(allWords.flatMap((word) => word.types))];
 
   return (
     <div>
@@ -162,10 +164,10 @@ const Area = ({ exerciseID }) => {
           gap: "var(--u-md)",
         }}
       >
-        {visibleWords.map(({ name, type }, index) => (
+        {visibleWords.map(({ name, types }, index) => (
           <WordBox
             name={name}
-            type={type}
+            types={types}
             isDropped={isDropped(name)}
             key={`${name}-${index}`}
           />
diff --git a/gradesa/src/components/ui/dragdrop/dustbin.js b/gradesa/src/components/ui/dragdrop/dustbin.js
index d586cfa..7fe2e0f 100644
--- a/gradesa/src/components/ui/dragdrop/dustbin.js
+++ b/gradesa/src/components/ui/dragdrop/dustbin.js
@@ -38,20 +38,19 @@ export const Dustbin = memo(function Dustbin({
           {droppedItems.map((item, index) => {
             let itemStyle = { color: `var(--${color})` };
             if (isSubmitted) {
-              itemStyle =
-                item.type === correctType
-                  ? {
-                      backgroundColor: "#b3f0b3",
-                      color: "#1a5c1a",
-                      borderRadius: "4px",
-                      padding: "2px 6px",
-                    }
-                  : {
-                      backgroundColor: "#ffb3b3",
-                      color: "#7a0000",
-                      borderRadius: "4px",
-                      padding: "2px 6px",
-                    };
+              itemStyle = item.types.includes(correctType)
+                ? {
+                    backgroundColor: "#b3f0b3",
+                    color: "#1a5c1a",
+                    borderRadius: "4px",
+                    padding: "2px 6px",
+                  }
+                : {
+                    backgroundColor: "#ffb3b3",
+                    color: "#7a0000",
+                    borderRadius: "4px",
+                    padding: "2px 6px",
+                  };
             }
             return (
               <div
diff --git a/gradesa/src/components/ui/dragdrop/wordbox.js b/gradesa/src/components/ui/dragdrop/wordbox.js
index 2890112..8ffa2bd 100644
--- a/gradesa/src/components/ui/dragdrop/wordbox.js
+++ b/gradesa/src/components/ui/dragdrop/wordbox.js
@@ -2,17 +2,18 @@ import { memo } from "react";
 import { useDrag } from "react-dnd";
 import { wordbox } from "./dragdrop.css";
 
-export const WordBox = memo(function WordBox({ name, type, isDropped }) {
+export const WordBox = memo(function WordBox({ name, types, isDropped }) {
   const [{ opacity }, drag] = useDrag(
     () => ({
-      type,
-      item: { name, type },
+      // drag type only needs to match a dustbin's accept list; grading uses `types` instead
+      type: types[0],
+      item: { name, types },
       canDrag: !isDropped,
       collect: (monitor) => ({
         opacity: monitor.isDragging() ? 0.4 : 1,
       }),
     }),
-    [name, type, isDropped]
+    [name, types, isDropped]
   );
   return (
     <div