diff --git a/src/Tokenizer.js b/src/Tokenizer.js
index f01c1ca8d3..056cc3ff40 100644
--- a/src/Tokenizer.js
+++ b/src/Tokenizer.js
@@ -241,8 +241,11 @@ module.exports = class Tokenizer {
         // Backpedal if it does not belong in this list.
         if (i !== l - 1) {
           bnext = this.rules.block.listItemStart.exec(itemMatch[i + 1]);
-
-          if (bnext[1].length > bcurr[0].length || bnext[1].length > 3) {
+          if (
+            !this.options.pedantic
+              ? bnext[1].length > bcurr[0].length || bnext[1].length > 3
+              : bnext[1].length > bcurr[1].length
+          ) {
             // nested list
             itemMatch.splice(i, 2, itemMatch[i] + '\n' + itemMatch[i + 1]);
             i--;
diff --git a/test/specs/new/list_align_pedantic.html b/test/specs/new/list_align_pedantic.html
new file mode 100644
index 0000000000..e1e199a491
--- /dev/null
+++ b/test/specs/new/list_align_pedantic.html
@@ -0,0 +1,15 @@
+<ul>
+	<li>one
+		<ul>
+			<li>two</li>
+			<li>three</li>
+			<li>four
+				<ul>
+					<li>five</li>
+					<li>six</li>
+					<li>seven</li>
+				</ul>
+			</li>
+		</ul>
+	</li>
+</ul>
diff --git a/test/specs/new/list_align_pedantic.md b/test/specs/new/list_align_pedantic.md
new file mode 100644
index 0000000000..f5e85b4a31
--- /dev/null
+++ b/test/specs/new/list_align_pedantic.md
@@ -0,0 +1,10 @@
+---
+pedantic: true
+---
+- one
+ - two
+  - three
+    - four
+     - five
+      - six
+       - seven