diff --git a/src/Lexer.ts b/src/Lexer.ts
index a54910ab8d..89d439dc8c 100644
--- a/src/Lexer.ts
+++ b/src/Lexer.ts
@@ -16,8 +16,9 @@ export class _Lexer<ParserOutput = string, RendererOutput = string> {
     top: boolean;
   };
 
+  public inlineQueue: { src: string, tokens: Token[] }[];
+
   private tokenizer: _Tokenizer<ParserOutput, RendererOutput>;
-  private inlineQueue: { src: string, tokens: Token[] }[];
 
   constructor(options?: MarkedOptions<ParserOutput, RendererOutput>) {
     // TokenList cannot be created in one go
diff --git a/src/Tokenizer.ts b/src/Tokenizer.ts
index 34674e02da..4f176de664 100644
--- a/src/Tokenizer.ts
+++ b/src/Tokenizer.ts
@@ -380,19 +380,10 @@ export class _Tokenizer<ParserOutput = string, RendererOutput = string> {
           }
         }
 
-        let istask: RegExpExecArray | null = null;
-        // Check for task list items
-        if (this.options.gfm) {
-          istask = this.rules.other.listIsTask.exec(itemContents);
-          if (istask) {
-            itemContents = itemContents.replace(this.rules.other.listReplaceTask, '');
-          }
-        }
-
         list.items.push({
           type: 'list_item',
           raw,
-          task: !!istask,
+          task: !!this.options.gfm && this.rules.other.listIsTask.test(itemContents),
           loose: false,
           text: itemContents,
           tokens: [],
@@ -417,6 +408,19 @@ export class _Tokenizer<ParserOutput = string, RendererOutput = string> {
         this.lexer.state.top = false;
         item.tokens = this.lexer.blockTokens(item.text, []);
         if (item.task) {
+          // Remove checkbox markdown from item tokens
+          item.text = item.text.replace(this.rules.other.listReplaceTask, '');
+          if (item.tokens[0]?.type === 'text' || item.tokens[0]?.type === 'paragraph') {
+            item.tokens[0].raw = item.tokens[0].raw.replace(this.rules.other.listReplaceTask, '');
+            item.tokens[0].text = item.tokens[0].text.replace(this.rules.other.listReplaceTask, '');
+            for (let i = this.lexer.inlineQueue.length - 1; i >= 0; i--) {
+              if (this.rules.other.listIsTask.test(this.lexer.inlineQueue[i].src)) {
+                this.lexer.inlineQueue[i].src = this.lexer.inlineQueue[i].src.replace(this.rules.other.listReplaceTask, '');
+                break;
+              }
+            }
+          }
+
           const taskRaw = this.rules.other.listTaskCheckbox.exec(item.raw);
           if (taskRaw) {
             const checkboxToken: Tokens.Checkbox = {
diff --git a/src/rules.ts b/src/rules.ts
index acd6207396..2f95b80be2 100644
--- a/src/rules.ts
+++ b/src/rules.ts
@@ -46,7 +46,7 @@ export const other = {
   blockquoteSetextReplace2: /^ {0,3}>[ \t]?/gm,
   listReplaceTabs: /^\t+/,
   listReplaceNesting: /^ {1,4}(?=( {4})*[^ ])/g,
-  listIsTask: /^\[[ xX]\] /,
+  listIsTask: /^\[[ xX]\] +\S/,
   listReplaceTask: /^\[[ xX]\] +/,
   listTaskCheckbox: /\[[ xX]\]/,
   anyLine: /\n.*\n/,
diff --git a/test/specs/new/list_loose_tasks.html b/test/specs/new/list_loose_tasks.html
index f7bc47eb1b..1416f042ef 100644
--- a/test/specs/new/list_loose_tasks.html
+++ b/test/specs/new/list_loose_tasks.html
@@ -6,10 +6,9 @@
 <p><input type="checkbox" checked="" disabled=""> Task1</p>
 </li>
 <li>
-<p><input type="checkbox" disabled=""></p>
-<pre>Task2</pre>
+<p><input type="checkbox" disabled=""> <pre>Task2</pre></p>
 </li>
 <li>
-<p><input type="checkbox" disabled=""></p>
+<p>[ ]</p>
 </li>
 </ul>
diff --git a/test/specs/new/tasklist_blocks.html b/test/specs/new/tasklist_blocks.html
new file mode 100644
index 0000000000..6a8fb31f36
--- /dev/null
+++ b/test/specs/new/tasklist_blocks.html
@@ -0,0 +1,53 @@
+<h1>tight</h1>
+<ul>
+<li><input checked="" disabled="" type="checkbox"> # heading</li>
+<li><input checked="" disabled="" type="checkbox"> - list</li>
+<li><input checked="" disabled="" type="checkbox"> &gt; blockquote</li>
+<li><input checked="" disabled="" type="checkbox"> ---</li>
+<li><input checked="" disabled="" type="checkbox"> ```
+<pre><code></code></pre>
+</li>
+<li><input checked="" disabled="" type="checkbox"> [def]: <a href="https://example.com">https://example.com</a></li>
+<li><input checked="" disabled="" type="checkbox"> <div>
+<em>html</em>
+</div>
+*html*
+</li>
+<li><input checked="" disabled="" type="checkbox"> | a | b |
+|---|---|
+| 1 | 1 |</li>
+</ul>
+<h1>loose</h1>
+<ul>
+<li>
+<p><input checked="" disabled="" type="checkbox"> # heading</p>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> - list</p>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> &gt; blockquote</p>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> ---</p>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> ```</p>
+<pre><code>
+</code></pre>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> [def]: <a href="https://example.com">https://example.com</a></p>
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> <div>
+<em>html</em></p>
+</div>
+*html*
+</li>
+<li>
+<p><input checked="" disabled="" type="checkbox"> | a | b |
+|---|---|
+| 1 | 1 |</p>
+</li>
+</ul>
diff --git a/test/specs/new/tasklist_blocks.md b/test/specs/new/tasklist_blocks.md
new file mode 100644
index 0000000000..488a461220
--- /dev/null
+++ b/test/specs/new/tasklist_blocks.md
@@ -0,0 +1,40 @@
+# tight
+
+- [x] # heading
+- [x] - list
+- [x] > blockquote
+- [x] ---
+- [x] ```
+  ```
+- [x] [def]: https://example.com
+- [x] <div>
+  *html*
+  </div>
+  *html*
+- [x] | a | b |
+  |---|---|
+  | 1 | 1 |
+
+# loose
+
+- [x] # heading
+
+- [x] - list
+
+- [x] > blockquote
+
+- [x] ---
+
+- [x] ```
+  ```
+
+- [x] [def]: https://example.com
+
+- [x] <div>
+  *html*
+  </div>
+  *html*
+
+- [x] | a | b |
+  |---|---|
+  | 1 | 1 |