diff --git a/src/wanikani.ts b/src/wanikani.ts
index 68457f0..7503baa 100644
--- a/src/wanikani.ts
+++ b/src/wanikani.ts
@@ -433,6 +433,7 @@ export class WaniKani {
           ja: string;
           en: string;
         }[];
+        meaning: string;
       }
     >();
     vocabularies.map((v) => {
@@ -442,6 +443,10 @@ export class WaniKani {
       sentenceMap.set(v.data.characters, {
         ...sent,
         sentences: v.data.context_sentences,
+        meaning: v.data.meanings
+          .sort((m1, m2) => Number(m2.primary) - Number(m1.primary))
+          .map((m) => m.meaning)
+          .join('; '),
       });
     });
     if (!sentenceMap.size) return;
@@ -476,23 +481,38 @@ export class WaniKani {
                 [fields.sentenceEn]: sent.en,
               };
 
-              if (
-                fields.sentenceCloze &&
-                !n.fields[fields.sentenceCloze]?.value
-              ) {
-                const clozeChar = '__';
-                let newSent = sent.sentences
-                  .map(({ ja, en }) => `${ja}<br/>${en}`)
-                  .join('<br/>')
-                  .replace(cleanJa, clozeChar);
-
-                cleanJa.split(/[\p{sc=Hiragana}]+/gu).map((c) => {
-                  if (c) {
-                    newSent = newSent.replace(c, clozeChar);
-                  }
-                });
-
-                fieldUpdate[fields.sentenceCloze] = newSent;
+              if (fields.sentenceCloze) {
+                let clozeSent = n.fields[fields.sentenceCloze]?.value || '';
+
+                if (!clozeSent && sent.sentences.length) {
+                  const clozeChar = '__';
+                  let newSent = sent.sentences
+                    .map(({ ja, en }) => `${ja}<br/>${en}`)
+                    .join('<br/>')
+                    .replace(cleanJa, clozeChar);
+
+                  cleanJa.split(/[\p{sc=Hiragana}]+/gu).map((c) => {
+                    if (c) {
+                      newSent = newSent.replace(c, clozeChar);
+                    }
+                  });
+
+                  fieldUpdate[fields.sentenceCloze] = newSent;
+                  clozeSent = newSent;
+                }
+
+                const notJa = '[^\\p{sc=Han}\\p{sc=Katakana}\\p{sc=Hiragana}]+';
+
+                if (
+                  clozeSent &&
+                  !new RegExp(
+                    `(^${notJa}<br/?>|<br/?><br/?>${notJa}$)`,
+                    'u',
+                  ).test(clozeSent)
+                ) {
+                  fieldUpdate[fields.sentenceCloze] =
+                    sent.meaning + '<br><br>' + clozeSent;
+                }
               }
 
               notesToUpdate.push({