diff --git a/app/ap_object.py b/app/ap_object.py
index a4bbab1..67543cb 100644
--- a/app/ap_object.py
+++ b/app/ap_object.py
@@ -6,7 +6,7 @@ from typing import Any
 
 import pydantic
 from bs4 import BeautifulSoup  # type: ignore
-from markdown import markdown
+from mistletoe import markdown  # type: ignore
 
 from app import activitypub as ap
 from app.actor import LOCAL_ACTOR
@@ -176,7 +176,7 @@ class Object:
 
         # PeerTube returns the content as markdown
         if self.ap_object.get("mediaType") == "text/markdown":
-            content = markdown(content, extensions=["mdx_linkify"])
+            content = markdown(content)
 
         return content
 
diff --git a/app/config.py b/app/config.py
index 84d0c49..993d5e0 100644
--- a/app/config.py
+++ b/app/config.py
@@ -12,7 +12,7 @@ from fastapi import HTTPException
 from fastapi import Request
 from itsdangerous import URLSafeTimedSerializer
 from loguru import logger
-from markdown import markdown
+from mistletoe import markdown  # type: ignore
 
 from app.utils.emoji import _load_emojis
 from app.utils.version import get_version_commit
@@ -158,9 +158,7 @@ ALSO_KNOWN_AS = CONFIG.also_known_as
 
 INBOX_RETENTION_DAYS = CONFIG.inbox_retention_days
 CUSTOM_FOOTER = (
-    markdown(
-        CONFIG.custom_footer.replace("{version}", VERSION), extensions=["mdx_linkify"]
-    )
+    markdown(CONFIG.custom_footer.replace("{version}", VERSION))
     if CONFIG.custom_footer
     else None
 )
diff --git a/docs/templates/layout.html b/docs/templates/layout.html
index 65860ea..07845e4 100644
--- a/docs/templates/layout.html
+++ b/docs/templates/layout.html
@@ -63,7 +63,7 @@ nav a:hover, main a:hover, header p a:hover {
     max-width: 960px;
     margin: 50px auto;
 }
-pre code {
+pre {
     padding: 10px;
     overflow: auto;
     display: block;
diff --git a/poetry.lock b/poetry.lock
index fdf0378..a8e62fb 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -26,7 +26,7 @@ tz = ["python-dateutil"]
 
 [[package]]
 name = "anyio"
-version = "3.6.1"
+version = "3.6.2"
 description = "High level compatibility layer for multiple asynchronous event loop implementations"
 category = "main"
 optional = false
@@ -39,7 +39,7 @@ sniffio = ">=1.1"
 [package.extras]
 doc = ["packaging", "sphinx-rtd-theme", "sphinx-autodoc-typehints (>=1.2.0)"]
 test = ["coverage[toml] (>=4.5)", "hypothesis (>=4.0)", "pytest (>=7.0)", "pytest-mock (>=3.6.1)", "trustme", "contextlib2", "uvloop (<0.15)", "mock (>=4)", "uvloop (>=0.15)"]
-trio = ["trio (>=0.16)"]
+trio = ["trio (>=0.16,<0.22)"]
 
 [[package]]
 name = "asgiref"
@@ -98,11 +98,11 @@ lxml = ["lxml"]
 
 [[package]]
 name = "black"
-version = "22.8.0"
+version = "22.10.0"
 description = "The uncompromising code formatter."
 category = "dev"
 optional = false
-python-versions = ">=3.6.2"
+python-versions = ">=3.7"
 
 [package.dependencies]
 click = ">=8.0.0"
@@ -286,7 +286,7 @@ doc = ["sphinx", "sphinx-rtd-theme", "sphinxcontrib-spelling"]
 
 [[package]]
 name = "faker"
-version = "15.0.0"
+version = "15.1.1"
 description = "Faker is a Python package that generates fake data for you."
 category = "dev"
 optional = false
@@ -348,7 +348,7 @@ python-versions = ">=3.6"
 
 [[package]]
 name = "greenlet"
-version = "1.1.3"
+version = "1.1.3.post0"
 description = "Lightweight in-process concurrent programming"
 category = "main"
 optional = false
@@ -498,7 +498,7 @@ python-versions = "*"
 
 [[package]]
 name = "invoke"
-version = "1.7.1"
+version = "1.7.3"
 description = "Pythonic task execution"
 category = "main"
 optional = false
@@ -596,17 +596,6 @@ babel = ["babel"]
 lingua = ["lingua"]
 testing = ["pytest"]
 
-[[package]]
-name = "markdown"
-version = "3.4.1"
-description = "Python implementation of Markdown."
-category = "main"
-optional = false
-python-versions = ">=3.7"
-
-[package.extras]
-testing = ["coverage", "pyyaml"]
-
 [[package]]
 name = "markupsafe"
 version = "2.1.1"
@@ -623,18 +612,6 @@ category = "dev"
 optional = false
 python-versions = "*"
 
-[[package]]
-name = "mdx-linkify"
-version = "2.1"
-description = "Link recognition for Python Markdown"
-category = "main"
-optional = false
-python-versions = "*"
-
-[package.dependencies]
-bleach = ">=3.1.0"
-Markdown = ">=3.0"
-
 [[package]]
 name = "mf2py"
 version = "1.1.2"
@@ -999,7 +976,7 @@ python-versions = ">=3.6"
 
 [[package]]
 name = "sqlalchemy"
-version = "1.4.41"
+version = "1.4.42"
 description = "Database Abstraction Library"
 category = "main"
 optional = false
@@ -1031,7 +1008,7 @@ sqlcipher = ["sqlcipher3-binary"]
 
 [[package]]
 name = "sqlalchemy2-stubs"
-version = "0.0.2a27"
+version = "0.0.2a29"
 description = "Typing Stubs for SQLAlchemy 1.4"
 category = "dev"
 optional = false
@@ -1094,7 +1071,7 @@ python-versions = ">=3.7"
 
 [[package]]
 name = "types-bleach"
-version = "5.0.3"
+version = "5.0.3.1"
 description = "Typing stubs for bleach"
 category = "dev"
 optional = false
@@ -1118,7 +1095,7 @@ python-versions = "*"
 
 [[package]]
 name = "types-markdown"
-version = "3.4.2"
+version = "3.4.2.1"
 description = "Typing stubs for Markdown"
 category = "dev"
 optional = false
@@ -1126,7 +1103,7 @@ python-versions = "*"
 
 [[package]]
 name = "types-pillow"
-version = "9.2.2"
+version = "9.2.2.2"
 description = "Typing stubs for Pillow"
 category = "dev"
 optional = false
@@ -1134,7 +1111,7 @@ python-versions = "*"
 
 [[package]]
 name = "types-python-dateutil"
-version = "2.8.19"
+version = "2.8.19.2"
 description = "Typing stubs for python-dateutil"
 category = "dev"
 optional = false
@@ -1142,7 +1119,7 @@ python-versions = "*"
 
 [[package]]
 name = "types-requests"
-version = "2.28.11"
+version = "2.28.11.2"
 description = "Typing stubs for requests"
 category = "dev"
 optional = false
@@ -1161,7 +1138,7 @@ python-versions = "*"
 
 [[package]]
 name = "types-urllib3"
-version = "1.26.25"
+version = "1.26.25.1"
 description = "Typing stubs for urllib3"
 category = "dev"
 optional = false
@@ -1169,7 +1146,7 @@ python-versions = "*"
 
 [[package]]
 name = "typing-extensions"
-version = "4.3.0"
+version = "4.4.0"
 description = "Backported and Experimental Type Hints for Python 3.7+"
 category = "main"
 optional = false
@@ -1236,7 +1213,7 @@ watchmedo = ["PyYAML (>=3.10)"]
 
 [[package]]
 name = "watchfiles"
-version = "0.17.0"
+version = "0.18.0"
 description = "Simple, modern and high performance file watching and code reload in python."
 category = "main"
 optional = false
@@ -1283,7 +1260,7 @@ dev = ["pytest (>=4.6.2)", "black (>=19.3b0)"]
 [metadata]
 lock-version = "1.1"
 python-versions = "^3.10"
-content-hash = "bc8585a0da6f4d4e54afafde1da287ed75ed6544981d11bba561a7678bc31b8f"
+content-hash = "89df524a545a19a20440d1872c93151bbf3f68d3b3d20cc50bc9049dd0e6d25f"
 
 [metadata.files]
 aiosqlite = [
@@ -1292,8 +1269,8 @@ aiosqlite = [
 ]
 alembic = []
 anyio = [
-    {file = "anyio-3.6.1-py3-none-any.whl", hash = "sha256:cb29b9c70620506a9a8f87a309591713446953302d7d995344d0d7c6c0c9a7be"},
-    {file = "anyio-3.6.1.tar.gz", hash = "sha256:413adf95f93886e442aea925f3ee43baa5a765a64a0f52c6081894f9992fdd0b"},
+    {file = "anyio-3.6.2-py3-none-any.whl", hash = "sha256:fbbe32bd270d2a2ef3ed1c5d45041250284e31fc0a4df4a5a6071842051a51e3"},
+    {file = "anyio-3.6.2.tar.gz", hash = "sha256:25ea0d673ae30af41a0c442f81cf3b38c7e79fdc7b60335a4c14e05eb0947421"},
 ]
 asgiref = [
     {file = "asgiref-3.5.2-py3-none-any.whl", hash = "sha256:1d2880b792ae8757289136f1db2b7b99100ce959b2aa57fd69dab783d05afac4"},
@@ -1321,29 +1298,27 @@ beautifulsoup4 = [
     {file = "beautifulsoup4-4.11.1.tar.gz", hash = "sha256:ad9aa55b65ef2808eb405f46cf74df7fcb7044d5cbc26487f96eb2ef2e436693"},
 ]
 black = [
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-    {file = "black-22.8.0-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:5107ea36b2b61917956d018bd25129baf9ad1125e39324a9b18248d362156a27"},
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-    {file = "black-22.8.0-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:dd82842bb272297503cbec1a2600b6bfb338dae017186f8f215c8958f8acf869"},
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+    {file = "black-22.10.0-cp39-cp39-macosx_11_0_arm64.whl", hash = "sha256:974308c58d057a651d182208a484ce80a26dac0caef2895836a92dd6ebd725e0"},
+    {file = "black-22.10.0-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:72ef3925f30e12a184889aac03d77d031056860ccae8a1e519f6cbb742736383"},
+    {file = "black-22.10.0-cp39-cp39-win_amd64.whl", hash = "sha256:432247333090c8c5366e69627ccb363bc58514ae3e63f7fc75c54b1ea80fa7de"},
+    {file = "black-22.10.0-py3-none-any.whl", hash = "sha256:c957b2b4ea88587b46cf49d1dc17681c1e672864fd7af32fc1e9664d572b3458"},
+    {file = "black-22.10.0.tar.gz", hash = "sha256:f513588da599943e0cde4e32cc9879e825d58720d6557062d1098c5ad80080e1"},
 ]
 bleach = [
     {file = "bleach-5.0.1-py3-none-any.whl", hash = "sha256:085f7f33c15bd408dd9b17a4ad77c577db66d76203e5984b1bd59baeee948b2a"},
@@ -1530,8 +1505,8 @@ factory-boy = [
     {file = "factory_boy-3.2.1.tar.gz", hash = "sha256:a98d277b0c047c75eb6e4ab8508a7f81fb03d2cb21986f627913546ef7a2a55e"},
 ]
 faker = [
-    {file = "Faker-15.0.0-py3-none-any.whl", hash = "sha256:84c83f0ac1a2c8ecabd784c501aa0ef1d082d4aee52c3d797d586081c166434c"},
-    {file = "Faker-15.0.0.tar.gz", hash = "sha256:245fc7d23470dc57164bd9a59b7b1126e16289ffcf813d88a6c8e9b8a37ea3fb"},
+    {file = "Faker-15.1.1-py3-none-any.whl", hash = "sha256:096c15e136adb365db24d8c3964fe26bfc68fe060c9385071a339f8c14e09c8a"},
+    {file = "Faker-15.1.1.tar.gz", hash = "sha256:a741b77f484215c3aab2604100669657189548f440fcb2ed0f8b7ee21c385629"},
 ]
 fastapi = [
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@@ -1546,60 +1521,72 @@ flake8 = [
 ]
 frozendict = []
 greenlet = [
-    {file = "greenlet-1.1.3-cp27-cp27m-macosx_10_14_x86_64.whl", hash = "sha256:8c287ae7ac921dfde88b1c125bd9590b7ec3c900c2d3db5197f1286e144e712b"},
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-    {file = "greenlet-1.1.3-cp27-cp27mu-manylinux1_x86_64.whl", hash = "sha256:510c3b15587afce9800198b4b142202b323bf4b4b5f9d6c79cb9a35e5e3c30d2"},
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+    {file = "watchfiles-0.18.0-pp38-pypy38_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:78b1e7c29b92dfc8fc32f15949019232b493767d236c2bff31848df13fdb9e8a"},
+    {file = "watchfiles-0.18.0-pp38-pypy38_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:27d64a6ed5e0aebef97c70fa3899a6958d4f7f049effc659e7dc3e81f3170a7b"},
+    {file = "watchfiles-0.18.0-pp39-pypy39_pp73-macosx_10_7_x86_64.whl", hash = "sha256:4bbc8bfa0f3871b1867af42837a5635a9c1cbb2b68d039754b4750642c34aaee"},
+    {file = "watchfiles-0.18.0-pp39-pypy39_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:9d3a12e4de5446fb6e286b720d0cb3a080811caf0ef43e556c2db5fe10ef0342"},
+    {file = "watchfiles-0.18.0-pp39-pypy39_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:9e611a90482ac14ef3ec234c1604ed921d1b0c68970eba82f1cf0d59a3e4eb76"},
+    {file = "watchfiles-0.18.0.tar.gz", hash = "sha256:bbe10d134eef1666451382015e48f092c941a6d4562a98ffa1a288f79a897c46"},
 ]
 wcwidth = [
     {file = "wcwidth-0.2.5-py2.py3-none-any.whl", hash = "sha256:beb4802a9cebb9144e99086eff703a642a13d6a0052920003a230f3294bbe784"},
diff --git a/pyproject.toml b/pyproject.toml
index a9a050c..954e88b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -18,7 +18,6 @@ httpx = {extras = ["http2"], version = "^0.23.0"}
 SQLAlchemy = {extras = ["asyncio"], version = "^1.4.39"}
 alembic = "^1.8.0"
 bleach = "^5.0.0"
-Markdown = "^3.3.7"
 prompt-toolkit = "^3.0.29"
 tomli-w = "^1.0.0"
 python-dateutil = "^2.8.2"
@@ -27,7 +26,6 @@ html5lib = "^1.1"
 mf2py = "^1.1.2"
 Pygments = "^2.12.0"
 loguru = "^0.6.0"
-mdx-linkify = "^2.1"
 Pillow = "^9.1.1"
 blurhash-python = "^1.1.3"
 html2text = "^2020.1.16"
diff --git a/scripts/build_docs.py b/scripts/build_docs.py
index 7e56f99..075077e 100644
--- a/scripts/build_docs.py
+++ b/scripts/build_docs.py
@@ -1,19 +1,115 @@
+import re
 import shutil
+import typing
 from pathlib import Path
+from typing import Any
 
 from jinja2 import Environment
 from jinja2 import FileSystemLoader
 from jinja2 import select_autoescape
-from markdown import markdown
+from mistletoe import Document  # type: ignore
+from mistletoe import HTMLRenderer  # type: ignore
+from mistletoe import block_token  # type: ignore
+from pygments import highlight  # type: ignore
+from pygments.formatters import HtmlFormatter  # type: ignore
+from pygments.lexers import get_lexer_by_name as get_lexer  # type: ignore
+from pygments.lexers import guess_lexer  # type: ignore
 
 from app.config import VERSION
+from app.source import CustomRenderer
 from app.utils.datetime import now
 
+_FORMATTER = HtmlFormatter()
+_FORMATTER.noclasses = True
 
-def markdownify(content: str) -> str:
-    return markdown(
-        content, extensions=["mdx_linkify", "fenced_code", "codehilite", "toc"]
-    )
+
+class DocRenderer(CustomRenderer):
+    def __init__(
+        self,
+        depth=5,
+        omit_title=True,
+        filter_conds=[],
+    ) -> None:
+        super().__init__(
+            enable_mentionify=False,
+            enable_hashtagify=False,
+        )
+        self._headings: list[tuple[int, str, str]] = []
+        self._ids: set[str] = set()
+        self.depth = depth
+        self.omit_title = omit_title
+        self.filter_conds = filter_conds
+
+    @property
+    def toc(self):
+        """
+        Returns table of contents as a block_token.List instance.
+        """
+
+        def get_indent(level):
+            if self.omit_title:
+                level -= 1
+            return " " * 4 * (level - 1)
+
+        def build_list_item(heading):
+            level, content, title_id = heading
+            template = '{indent}- <a href="#{id}" rel="nofollow">{content}</a>\n'
+            return template.format(
+                indent=get_indent(level), content=content, id=title_id
+            )
+
+        lines = [build_list_item(heading) for heading in self._headings]
+        items = block_token.tokenize(lines)
+        return items[0]
+
+    def render_heading(self, token):
+        """
+        Overrides super().render_heading; stores rendered heading first,
+        then returns it.
+        """
+        template = '<h{level} id="{id}">{inner}</h{level}>'
+        inner = self.render_inner(token)
+        title_id = inner.lower().replace(" ", "-")
+        if title_id in self._ids:
+            i = 1
+            while 1:
+                title_id = f"{title_id}_{i}"
+                if title_id not in self._ids:
+                    break
+        self._ids.add(title_id)
+        rendered = template.format(level=token.level, inner=inner, id=title_id)
+        content = self.parse_rendered_heading(rendered)
+
+        if not (
+            self.omit_title
+            and token.level == 1
+            or token.level > self.depth
+            or any(cond(content) for cond in self.filter_conds)
+        ):
+            self._headings.append((token.level, content, title_id))
+        return rendered
+
+    @staticmethod
+    def parse_rendered_heading(rendered):
+        """
+        Helper method; converts rendered heading to plain text.
+        """
+        return re.sub(r"<.+?>", "", rendered)
+
+    def render_block_code(self, token: typing.Any) -> str:
+        code = token.children[0].content
+        lexer = get_lexer(token.language) if token.language else guess_lexer(code)
+        return highlight(code, lexer, _FORMATTER)
+
+
+def markdownify(content: str) -> tuple[str, Any]:
+    with DocRenderer() as renderer:
+        rendered_content = renderer.render(Document(content))
+
+    with HTMLRenderer() as html_renderer:
+        toc = html_renderer.render(renderer.toc)
+
+    return rendered_content, toc
 
 
 def main() -> None:
@@ -30,32 +126,36 @@ def main() -> None:
     last_updated = now().replace(second=0, microsecond=0).isoformat()
 
     readme = Path("README.md")
+    content, toc = markdownify(readme.read_text().removeprefix("# microblog.pub"))
     template.stream(
-        content=markdownify(readme.read_text().removeprefix("# microblog.pub")),
+        content=content,
         version=VERSION,
         path="/",
         last_updated=last_updated,
     ).dump("docs/dist/index.html")
 
     install = Path("docs/install.md")
+    content, toc = markdownify(install.read_text())
     template.stream(
-        content=markdownify(install.read_text()),
+        content=content.replace("[TOC]", toc),
         version=VERSION,
         path="/installing.html",
         last_updated=last_updated,
     ).dump("docs/dist/installing.html")
 
     user_guide = Path("docs/user_guide.md")
+    content, toc = markdownify(user_guide.read_text())
     template.stream(
-        content=markdownify(user_guide.read_text()),
+        content=content.replace("[TOC]", toc),
         version=VERSION,
         path="/user_guide.html",
         last_updated=last_updated,
     ).dump("docs/dist/user_guide.html")
 
     developer_guide = Path("docs/developer_guide.md")
+    content, toc = markdownify(developer_guide.read_text())
     template.stream(
-        content=markdownify(developer_guide.read_text()),
+        content=content.replace("[TOC]", toc),
         version=VERSION,
         path="/developer_guide.html",
         last_updated=last_updated,