diff --git a/src/emitter.ts b/src/emitter.ts
index 0301f34..9a3002c 100644
--- a/src/emitter.ts
+++ b/src/emitter.ts
@@ -16,11 +16,18 @@ import type {
   CommentNode,
 } from './node-types';
 
+const getIndentMatcher = unaryMemoize(
+  (length: number) => new RegExp(String.raw`\n[\p{Space_Separator}\t]{1,${length}}`, 'gu'),
+  Array.from({ length: 20 }, (_, i) => i + 1)
+);
+
 export class Emitter {
   str: string;
+  indent: number;
 
   constructor() {
     this.str = '';
+    this.indent = 0;
   }
 
   emit(node: Node | Node[]) {
@@ -106,7 +113,10 @@ export class Emitter {
   emitListItem(li: OrderedListItemNode | UnorderedListItemNode) {
     const attrs = li.attrs.map(a => ` ${a.key}=${JSON.stringify(a.value)}`).join('');
     this.str += `<li${attrs}>`;
+    const oldIndent = this.indent;
+    this.indent = li.contentsIndent;
     this.emitFragment(li.contents);
+    this.indent = oldIndent;
     if (li.sublist !== null) {
       if (li.sublist.name === 'ol') {
         this.emitOrderedList(li.sublist);
@@ -130,7 +140,12 @@ export class Emitter {
   }
 
   emitText(text: TextNode) {
-    this.str += text.contents;
+    let contents = text.contents;
+    if (this.indent) {
+      const indentMatcher = getIndentMatcher(this.indent);
+      contents = contents.replace(indentMatcher, '\n');
+    }
+    this.str += contents;
   }
 
   emitTick(node: TickNode) {
@@ -165,3 +180,15 @@ export class Emitter {
     this.str += `</${wrapping}>`;
   }
 }
+
+function unaryMemoize<K, V>(fn: (arg: K) => V, prepopulate: K[] = []) {
+  const cache = new Map(prepopulate.map(arg => [arg, fn(arg)]));
+  return (arg: K) => {
+    let value = cache.get(arg);
+    if (value === undefined && !cache.has(arg)) {
+      value = fn(arg);
+      cache.set(arg, value);
+    }
+    return value as V;
+  };
+}
diff --git a/src/node-types.ts b/src/node-types.ts
index cf2000a..9393aaf 100644
--- a/src/node-types.ts
+++ b/src/node-types.ts
@@ -188,6 +188,7 @@ export type OrderedListNode = {
 export type UnorderedListItemNode = {
   name: 'unordered-list-item';
   contents: FragmentNode[];
+  contentsIndent: number;
   sublist: ListNode | null;
   attrs: { key: string; value: string; location: LocationRange }[];
   location: LocationRange;
@@ -196,6 +197,7 @@ export type UnorderedListItemNode = {
 export type OrderedListItemNode = {
   name: 'ordered-list-item';
   contents: FragmentNode[];
+  contentsIndent: number;
   sublist: ListNode | null;
   attrs: { key: string; value: string; location: LocationRange }[];
   location: LocationRange;
diff --git a/src/parser.ts b/src/parser.ts
index 5ba5065..861ada8 100644
--- a/src/parser.ts
+++ b/src/parser.ts
@@ -79,12 +79,15 @@ export class Parser {
     const startTok = this._t.peek() as OrderedListToken | UnorderedListToken;
 
     let node: Unlocated<ListNode>;
+    let contentsIndent: number;
     if (startTok.name === 'ul') {
       const match = startTok.contents.match(/(\s*)\* /);
       node = { name: 'ul', indent: match![1].length, contents: [] };
+      contentsIndent = match![0].length;
     } else {
       const match = startTok.contents.match(/(\s*)([^.]+)\. /);
       node = { name: 'ol', indent: match![1].length, start: Number(match![2]), contents: [] };
+      contentsIndent = match![0].length;
     }
 
     while (true) {
@@ -101,15 +104,19 @@ export class Parser {
       }
 
       // @ts-ignore typescript is not smart enough to figure out that the types line up
-      node.contents.push(this.parseListItem(node.name, node.indent));
+      node.contents.push(this.parseListItem(node.name, node.indent, contentsIndent));
     }
 
     return this.finish(node);
   }
 
-  parseListItem(kind: 'ol', indent: number): OrderedListItemNode;
-  parseListItem(kind: 'ul', indent: number): UnorderedListItemNode;
-  parseListItem(kind: 'ol' | 'ul', indent: number): OrderedListItemNode | UnorderedListItemNode {
+  parseListItem(kind: 'ol', indent: number, contentsIndent: number): OrderedListItemNode;
+  parseListItem(kind: 'ul', indent: number, contentsIndent: number): UnorderedListItemNode;
+  parseListItem(
+    kind: 'ol' | 'ul',
+    indent: number,
+    contentsIndent: number
+  ): OrderedListItemNode | UnorderedListItemNode {
     this.pushPos();
     // consume list token
     this._t.next();
@@ -132,7 +139,7 @@ export class Parser {
 
     let name: 'ordered-list-item' | 'unordered-list-item' =
       kind === 'ol' ? 'ordered-list-item' : 'unordered-list-item';
-    return this.finish({ name, contents, sublist, attrs });
+    return this.finish({ name, contents, contentsIndent, sublist, attrs });
   }
 
   parseFragment(opts: ParseFragmentOpts): FragmentNode[];
diff --git a/test/cases/list-item-deindenting.raw.ecmarkdown b/test/cases/list-item-deindenting.raw.ecmarkdown
new file mode 100644
index 0000000..f88c0dd
--- /dev/null
+++ b/test/cases/list-item-deindenting.raw.ecmarkdown
@@ -0,0 +1,22 @@
+1. Item 1
+  1. Item 1a
+     (multi-line)
+  1. Item 1b
+     (also multi-line)
+       ...and extra-indented
+1. Item 2
+    1. Item 2a
+       (multi-line)
+    1. Item 2b
+       (also multi-line)
+         ...and extra-indented
+1. Item 3
+  (multi-line but under-indented)
+1. Item 4
+  * unordered item
+    (multi-line)
+  * unordered item
+      (multi-line and extra-indented)
+    ...partially
+  * unordered item
+   (multi-line and under-indented)
diff --git a/test/cases/list-item-deindenting.raw.html b/test/cases/list-item-deindenting.raw.html
new file mode 100644
index 0000000..9d224db
--- /dev/null
+++ b/test/cases/list-item-deindenting.raw.html
@@ -0,0 +1,12 @@
+<ol><li>Item 1<ol><li>Item 1a
+(multi-line)</li><li>Item 1b
+(also multi-line)
+  ...and extra-indented</li></ol></li><li>Item 2<ol><li>Item 2a
+(multi-line)</li><li>Item 2b
+(also multi-line)
+  ...and extra-indented</li></ol></li><li>Item 3
+(multi-line but under-indented)</li><li>Item 4<ul><li>unordered item
+(multi-line)</li><li>unordered item
+  (multi-line and extra-indented)
+...partially</li><li>unordered item
+(multi-line and under-indented)</li></ul></li></ol>
diff --git a/test/parser.js b/test/parser.js
index 0d8d5f3..5eced82 100644
--- a/test/parser.js
+++ b/test/parser.js
@@ -59,6 +59,7 @@ describe('Parser', function () {
           {
             name: 'ordered-list-item',
             attrs: [],
+            contentsIndent: 3,
             contents: [
               {
                 contents: 'Foo. ',
diff --git a/test/run-cases.js b/test/run-cases.js
index d9a5be6..737b5d5 100644
--- a/test/run-cases.js
+++ b/test/run-cases.js
@@ -22,7 +22,7 @@ describe('baselines', () => {
         ? ecmarkdown.fragment
         : ecmarkdown.algorithm;
       let rawOutput = processor(input);
-      let output = beautify(rawOutput);
+      let output = file.endsWith('.raw.ecmarkdown') ? rawOutput + '\n' : beautify(rawOutput);
       let existing = fs.existsSync(snapshotFile) ? fs.readFileSync(snapshotFile, 'utf8') : null;
       if (shouldUpdate) {
         if (existing !== output) {