diff --git a/src/constants/regular-expressions.ts b/src/constants/regular-expressions.ts
index a896237e..f470ccba 100644
--- a/src/constants/regular-expressions.ts
+++ b/src/constants/regular-expressions.ts
@@ -3,4 +3,11 @@
  */
 const REGEX_LINE_BREAKS = /(?:\r\n|\r|\n)/g
 
-export { REGEX_LINE_BREAKS }
+/**
+ * A regex for standard punctuation characters for US-ASCII plus unicode punctuation.
+ *
+ * @see https://stackoverflow.com/a/25575009
+ */
+const REGEX_PUNCTUATION = /[\u2000-\u206f\u2e00-\u2e7f'!"#$%&()*+,\-./:;<=>?@\\[\]^_`{|}~]/
+
+export { REGEX_LINE_BREAKS, REGEX_PUNCTUATION }
diff --git a/src/serializers/markdown/markdown.test.ts b/src/serializers/markdown/markdown.test.ts
index c18de1d3..1c3f9f40 100644
--- a/src/serializers/markdown/markdown.test.ts
+++ b/src/serializers/markdown/markdown.test.ts
@@ -11,6 +11,13 @@ import { createMarkdownSerializer } from './markdown'
 
 import type { MarkdownSerializerReturnType } from './markdown'
 
+const HTML_INPUT_SPECIAL_HTML_CHARS = `Ambition &amp; Balance<br>
+&lt;doist&gt;<br>
+&lt;/doist&gt;<br>
+&lt;doist&gt;&lt;/doist&gt;<br>
+&quot;Doist&quot;<br>
+&#39;Doist&#39;`
+
 const HTML_INPUT_HEADINGS = `<h1>Heading level 1</h1>
 <h2>Heading level 2</h2>
 <h3>Heading level 3</h3>
@@ -94,11 +101,6 @@ const HTML_INPUT_UNORDERED_LISTS = `<ul>
 </ul>
 <hr>
 <ul>
-<li>1968. A great year!</li>
-<li>I think 1969 was second best.</li>
-</ul>
-<hr>
-<ul>
 <li>This is the first list item.</li>
 <li>Here&#39;s the second list item.<br>  I need to add another paragraph below the second list item.</li>
 <li>And here&#39;s the third list item.</li>
@@ -137,11 +139,6 @@ const HTML_INPUT_TASK_LISTS = `<ul data-type="taskList">
 </ul>
 <hr>
 <ul data-type="taskList">
-<li data-type="taskItem" data-checked="false">1968. A great year!</li>
-<li data-type="taskItem" data-checked="true">I think 1969 was second best.</li>
-</ul>
-<hr>
-<ul data-type="taskList">
 <li data-type="taskItem" data-checked="false">This is the first list item.</li>
 <li data-type="taskItem" data-checked="false">Here&#39;s the second list item.<br>  I need to add another paragraph below the second list item.</li>
 <li data-type="taskItem" data-checked="false">And here&#39;s the third list item.</li>
@@ -183,29 +180,40 @@ const HTML_INPUT_LINKS = `<p>My favorite search engine is <a href="https://duckd
 
 const HTML_INPUT_STYLED_LINKS = `<p>I love supporting the <strong><a href="https://eff.org">EFF</a></strong>.<br>This is the <em><a href="https://www.markdownguide.org">Markdown Guide</a></em>.<br>See the section on <a href="#code"><code>code</code></a>.</p>`
 
-describe('Markdown Serializer', () => {
-    const HTML_INPUT_SPECIAL_HTML_CHARS = `Ambition &amp; Balance<br>
-&lt;doist&gt;<br>
-&lt;/doist&gt;<br>
-&lt;doist&gt;&lt;/doist&gt;<br>
-&quot;Doist&quot;<br>
-&#39;Doist&#39;`
-
-    const HTML_INPUT_SPECIAL_MARKDOWN_CHARS = `before \\ after<br>
-before * after<br>
-- after<br>
-+ after<br>
-= after<br>
-=== after<br>
-\` after <br>
-~~~ after<br>
-before [ after<br>
-before ] after<br>
-> after<br>
-before _ after<br>
-1. after<br>
-99. after<br>`
+const HTML_INPUT_PONCTUATION_CHARACTERS = `<p>\\' text \\'</p>
+<p>\\! text \\!</p>
+<p>\\" text \\"</p>
+<p>\\# text \\#</p>
+<p>\\$ text \\$</p>
+<p>\\% text \\%</p>
+<p>\\&amp; text \\&amp;</p>
+<p>\\( text \\(</p>
+<p>\\) text \\)</p>
+<p>\\* text \\*</p>
+<p>\\+ text \\+</p>
+<p>\\, text \\,</p>
+<p>\\\\ text \\\\</p>
+<p>\\- text \\-</p>
+<p>\\. text \\.</p>
+<p>\\/ text \\/</p>
+<p>\\: text \\:</p>
+<p>\\; text \\;</p>
+<p>\\&lt; text \\&lt;</p>
+<p>\\= text \\=</p>
+<p>\\&gt; text \\&gt;</p>
+<p>\\? text \\?</p>
+<p>\\@ text \\@</p>
+<p>\\[ text \\[</p>
+<p>\\] text \\]</p>
+<p>\\^ text \\^</p>
+<p>\\_ text \\_</p>
+<p>\\\` text \\\`</p>
+<p>\\{ text \\{</p>
+<p>\\| text \\|</p>
+<p>\\} text \\}</p>
+<p>\\~ text \\~</p>`
 
+describe('Markdown Serializer', () => {
     describe('Plain-text Document', () => {
         describe('with default extensions', () => {
             let markdownSerializer: MarkdownSerializerReturnType
@@ -227,24 +235,6 @@ before _ after<br>
 'Doist'`)
             })
 
-            test('special Markdown characters are NOT escaped', () => {
-                expect(markdownSerializer.serialize(HTML_INPUT_SPECIAL_MARKDOWN_CHARS))
-                    .toBe(`before \\ after
-before * after
-- after
-+ after
-= after
-=== after
-\` after
-~~~ after
-before [ after
-before ] after
-> after
-before _ after
-1. after
-99. after`)
-            })
-
             test('paragraphs Markdown output is correct', () => {
                 expect(markdownSerializer.serialize(HTML_INPUT_PARAGRAPHS)).toBe(
                     `I really like using Markdown.
@@ -260,6 +250,49 @@ I think I'll use it to format all of my documents from now on.`,
                     replacement: expect.any(Function),
                 })
             })
+
+            describe('with overridden `escape` function', () => {
+                test('return the input as-is (escaping behaviour disabled)', () => {
+                    expect(
+                        markdownSerializer.serialize(`<p>- 1968. A great year!</p>
+<p>- I think 1969 was second best.</p>`),
+                    ).toBe(`- 1968. A great year!
+- I think 1969 was second best.`)
+                    expect(markdownSerializer.serialize(HTML_INPUT_PONCTUATION_CHARACTERS))
+                        .toBe(`\\' text \\'
+\\! text \\!
+\\" text \\"
+\\# text \\#
+\\$ text \\$
+\\% text \\%
+\\& text \\&
+\\( text \\(
+\\) text \\)
+\\* text \\*
+\\+ text \\+
+\\, text \\,
+\\\\ text \\\\
+\\- text \\-
+\\. text \\.
+\\/ text \\/
+\\: text \\:
+\\; text \\;
+\\< text \\<
+\\= text \\=
+\\> text \\>
+\\? text \\?
+\\@ text \\@
+\\[ text \\[
+\\] text \\]
+\\^ text \\^
+\\_ text \\_
+\\\` text \\\`
+\\{ text \\{
+\\| text \\|
+\\} text \\}
+\\~ text \\~`)
+                })
+            })
         })
 
         describe('with custom `*Suggestion` extensions', () => {
@@ -292,7 +325,7 @@ Answer: [Doist Frontend](channel://190200)`)
     })
 
     describe('Rich-text Document', () => {
-        describe('without default extensions', () => {
+        describe('with default extensions', () => {
             let markdownSerializer: MarkdownSerializerReturnType
 
             beforeEach(() => {
@@ -309,24 +342,6 @@ Answer: [Doist Frontend](channel://190200)`)
 'Doist'`)
             })
 
-            test('special Markdown characters are escaped', () => {
-                expect(markdownSerializer.serialize(HTML_INPUT_SPECIAL_MARKDOWN_CHARS))
-                    .toBe(`before \\\\ after
-before \\* after
-\\- after
-\\+ after
-\\= after
-\\=== after
-\\\` after
-\\~~~ after
-before \\[ after
-before \\] after
-\\> after
-before \\_ after
-1\\. after
-99\\. after`)
-            })
-
             test('headings Markdown output is correct', () => {
                 expect(markdownSerializer.serialize(HTML_INPUT_HEADINGS)).toBe(
                     '# Heading level 1\n\n## Heading level 2\n\n### Heading level 3\n\n#### Heading level 4\n\n##### Heading level 5\n\n###### Heading level 6',
@@ -427,11 +442,6 @@ Strikethrough uses two tildes: ~~scratch this~~`,
 
 ---
 
-- 1968\\. A great year!
-- I think 1969 was second best.
-
----
-
 - This is the first list item.
 - Here's the second list item.
     I need to add another paragraph below the second list item.
@@ -471,11 +481,6 @@ Strikethrough uses two tildes: ~~scratch this~~`,
 
 ---
 
--   1968\\. A great year!
--   I think 1969 was second best.
-
----
-
 -   This is the first list item.
 -   Here's the second list item.
     I need to add another paragraph below the second list item.
@@ -554,15 +559,83 @@ See the section on [\`code\`](#code).`,
                 )
             })
 
-            test('special Markdown characters are NOT escaped if `escape` is disabled', () => {
-                const customSerializer = createMarkdownSerializer(getSchema([RichTextKit]), {
-                    escape: false,
+            describe('with overridden `escape` function', () => {
+                test('backslash characters preceding punctuation characters are escaped correctly', () => {
+                    expect(markdownSerializer.serialize(HTML_INPUT_PONCTUATION_CHARACTERS))
+                        .toBe(`\\\\' text \\\\'
+
+\\\\! text \\\\!
+
+\\\\" text \\\\"
+
+\\\\# text \\\\#
+
+\\\\$ text \\\\$
+
+\\\\% text \\\\%
+
+\\\\& text \\\\&
+
+\\\\( text \\\\(
+
+\\\\) text \\\\)
+
+\\\\* text \\\\*
+
+\\\\+ text \\\\+
+
+\\\\, text \\\\,
+
+\\\\\\ text \\\\\\
+
+\\\\- text \\\\-
+
+\\\\. text \\\\.
+
+\\\\/ text \\\\/
+
+\\\\: text \\\\:
+
+\\\\; text \\\\;
+
+\\\\< text \\\\<
+
+\\\\= text \\\\=
+
+\\\\> text \\\\>
+
+\\\\? text \\\\?
+
+\\\\@ text \\\\@
+
+\\\\[ text \\\\[
+
+\\\\] text \\\\]
+
+\\\\^ text \\\\^
+
+\\\\_ text \\\\_
+
+\\\\\` text \\\\\`
+
+\\\\{ text \\\\{
+
+\\\\| text \\\\|
+
+\\\\} text \\\\}
+
+\\\\~ text \\\\~`)
+                })
+
+                test('text content that matches the ordered list syntax is escaped correctly', () => {
+                    expect(
+                        markdownSerializer.serialize(`<ul>
+<li>1968. A great year!</li>
+<li>I think 1969 was second best.</li>
+</ul>`),
+                    ).toBe(`- 1968\\. A great year!
+- I think 1969 was second best.`)
                 })
-                expect(
-                    customSerializer.serialize(
-                        `<p><strong>Wrapped markdown</strong> **still markdown**</p>`,
-                    ),
-                ).toBe(`**Wrapped markdown** **still markdown**`)
             })
         })
 
@@ -620,11 +693,6 @@ See the section on [\`code\`](#code).`,
 
 ---
 
--   1968\\. A great year!
--   I think 1969 was second best.
-
----
-
 -   This is the first list item.
 -   Here's the second list item.
     I need to add another paragraph below the second list item.
@@ -686,11 +754,6 @@ See the section on [\`code\`](#code).`,
 
 ---
 
-- [ ] 1968\\. A great year!
-- [x] I think 1969 was second best.
-
----
-
 - [ ] This is the first list item.
 - [ ] Here's the second list item.
     I need to add another paragraph below the second list item.
diff --git a/src/serializers/markdown/markdown.ts b/src/serializers/markdown/markdown.ts
index 94c06f59..e3a79c01 100644
--- a/src/serializers/markdown/markdown.ts
+++ b/src/serializers/markdown/markdown.ts
@@ -1,5 +1,6 @@
 import Turndown from 'turndown'
 
+import { REGEX_PUNCTUATION } from '../../constants/regular-expressions'
 import { isPlainTextDocument } from '../../helpers/schema'
 
 import { image } from './plugins/image'
@@ -11,16 +12,6 @@ import { taskItem } from './plugins/task-item'
 
 import type { Schema } from 'prosemirror-model'
 
-/**
- * The options that the `createMarkdownSerializer` function accepts.
- */
-type MarkdownSerializerOptions = {
-    /**
-     * Disables markdown escaping.
-     */
-    escape?: false
-}
-
 /**
  * The return type for the `createMarkdownSerializer` function.
  */
@@ -97,23 +88,41 @@ const INITIAL_TURNDOWN_OPTIONS: Turndown.Options = {
  *
  * @returns A normalized object for the Markdown serializer.
  */
-function createMarkdownSerializer(
-    schema: Schema,
-    options?: MarkdownSerializerOptions,
-): MarkdownSerializerReturnType {
+function createMarkdownSerializer(schema: Schema): MarkdownSerializerReturnType {
     // Initialize Turndown with custom options
     const turndown = new Turndown(INITIAL_TURNDOWN_OPTIONS)
 
-    // Turndown was built to convert HTML into Markdown, expecting the input to be standards
-    // compliant HTML. As such, it collapses all whitespace by default, and there's
-    // currently no way to opt-out of this behavior. However, for plain-text editors, we
-    // need to preserve Markdown whitespace (otherwise we lose syntax like nested lists) by
-    // replacing all instances of the space character (but only if it's preceded by another
-    // space character) by the non-breaking space character, and after processing the input
-    // with Turndown, we restore the original space character.
-    if (isPlainTextDocument(schema) || options?.escape === false) {
+    // Turndown ensures Markdown characters are escaped (i.e. `\`) by default, so they are not
+    // interpreted as Markdown when the output is compiled back to HTML. However, for plain-text
+    // editors, we need to override the `escape` function to return the input as-is (effectively
+    // disabling the escaping behaviour), so that all characters are interpreted as Markdown.
+    if (isPlainTextDocument(schema)) {
         turndown.escape = (str) => str
     }
+    // As for rich-text editors, we need to override the built-in escaping behaviour with a custom
+    // implementation to suit our requirements. Please note that the `escape` function takes the
+    // text content of each HTML element, with the exception of code elements, so we can be sure
+    // that the escaping behaviour will only touch relevant Markdown characters.
+    else {
+        turndown.escape = (str) => {
+            return (
+                str
+                    // Escape all backslash characters that precedes any punctuation characters,
+                    // otherwise the backslash character itself will be interpreted as escaping the
+                    // character that comes after it (which is not the intent). It's important that
+                    // this escape rule is executed before all other escape rules, otherwise we
+                    // could be double escaping some backslash characters.
+                    .replace(new RegExp(`(\\\\${REGEX_PUNCTUATION.source})`, 'g'), '\\$1')
+
+                    // Although the CommonMark specification allows for bulleted or ordered lists
+                    // inside other bulleted or ordered lists (i.e. `- 1. - 1. Item`), the markup
+                    // generated by Markdown compilers is not supported by Tiptap, and we need to
+                    // make sure that text context that matches the ordered list syntax is
+                    // correctly escaped in order to be interpreted as text.
+                    .replace(/^(\d+)\.(\s.+|$)/, '$1\\.$2')
+            )
+        }
+    }
 
     // Overwrite some built-in rules for handling of special behaviours
     // (see documentation for each extension for more details)