diff --git a/md2cf/__main__.py b/md2cf/__main__.py
index 7db41fb..f4453ad 100644
--- a/md2cf/__main__.py
+++ b/md2cf/__main__.py
@@ -16,6 +16,7 @@
 
 import md2cf.document
 from md2cf import api
+from md2cf.anchor import rewrite_page_anchors
 from md2cf.console_output import (
     console,
     error_console,
@@ -227,6 +228,15 @@ def get_parser():
         "existing and uploaded file, leave the link as-is instead of exiting.",
     )
 
+    anchor_group = parser.add_argument_group("anchor arguments")
+    anchor_group.add_argument(
+        "--convert-anchors",
+        action=argparse.BooleanOptionalAction,
+        default=True,
+        help="rewrite markdown-style fragment anchors to Confluence-native format. "
+        "Enabled by default. Use --no-convert-anchors to disable.",
+    )
+
     parser.add_argument(
         "--dry-run",
         action="store_true",
@@ -539,6 +549,9 @@ def pre_process_page(page, args, postface_markup, preface_markup, space_info):
     if postface_markup:
         page.body = page.body + postface_markup
 
+    if args.convert_anchors:
+        page.body = rewrite_page_anchors(page.body, page.title)
+
 
 def validate_relative_links(pages_to_upload, path_to_page):
     invalid_links = False
diff --git a/md2cf/anchor.py b/md2cf/anchor.py
new file mode 100644
index 0000000..4072fd3
--- /dev/null
+++ b/md2cf/anchor.py
@@ -0,0 +1,111 @@
+"""Rewrite markdown-style fragment anchors to Confluence-native anchor format.
+
+Confluence generates heading anchors as ``PageTitleStripped-HeadingStripped``
+where "stripped" means spaces and hyphens are removed but other characters
+(like parentheses) are kept, with original casing preserved.
+
+Example
+-------
+Page title : "SSH Reverse Tunnel Setup Guide - Embedded Hardware to AWS EC2"
+Heading    : "The Concept"
+
+Markdown anchor     : ``#the-concept``
+Confluence anchor   : ``#SSHReverseTunnelSetupGuideEmbeddedHardwaretoAWSEC2-TheConcept``
+"""
+
+from __future__ import annotations
+
+import html
+import re
+from urllib.parse import quote as _url_quote
+
+
+def _strip_for_anchor(text: str) -> str:
+    """Remove spaces and hyphens/dashes.
+
+    Confluence keeps other chars like parentheses.
+    """
+    return re.sub(r"[\s\-]", "", text)
+
+
+def _heading_to_markdown_anchor(text: str) -> str:
+    """Convert a heading string to a GitHub-Flavored-Markdown anchor slug."""
+    slug = text.lower()
+    slug = re.sub(r"[^\w\s-]", "", slug)
+    slug = re.sub(r"\s+", "-", slug)
+    return slug.strip("-")
+
+
+def _extract_headings(storage_body: str) -> list[str]:
+    """Return plain-text heading strings from Confluence storage-format HTML."""
+    headings: list[str] = []
+    for m in re.finditer(r"<h[1-6][^>]*>(.*?)</h[1-6]>", storage_body, re.DOTALL):
+        raw = re.sub(r"<[^>]+>", "", m.group(1))
+        text = html.unescape(raw).strip()
+        if text:
+            headings.append(text)
+    return headings
+
+
+def _build_anchor_map(storage_body: str, page_title: str) -> dict[str, str]:
+    """Build a mapping *markdown-anchor → confluence-anchor* for every heading.
+
+    Handles duplicate headings with GFM-style suffixes:
+    first "Setup" → ``#setup``, second → ``#setup-1``, etc.
+    """
+    title_part = _strip_for_anchor(page_title)
+    anchor_map: dict[str, str] = {}
+    seen_counts: dict[str, int] = {}
+
+    for heading in _extract_headings(storage_body):
+        md_base = _heading_to_markdown_anchor(heading)
+        if not md_base:
+            continue
+
+        count = seen_counts.get(md_base, 0)
+        md_anchor = md_base if count == 0 else f"{md_base}-{count}"
+        seen_counts[md_base] = count + 1
+
+        cf_base = f"{title_part}-{_strip_for_anchor(heading)}"
+        cf_anchor = cf_base if count == 0 else f"{cf_base}-{count}"
+
+        cf_anchor = _url_quote(cf_anchor, safe="-")
+
+        if cf_anchor and not cf_anchor[0].isalpha():
+            cf_anchor = f"id-{cf_anchor}"
+
+        if md_anchor != cf_anchor:
+            anchor_map[md_anchor] = cf_anchor
+
+    return anchor_map
+
+
+def _rewrite_anchors(storage_body: str, anchor_map: dict[str, str]) -> str:
+    """Replace markdown-style anchors with Confluence-style ones."""
+
+    def _replace_href(m: re.Match[str]) -> str:
+        anchor = m.group(1)
+        if anchor in anchor_map:
+            return f'href="#{anchor_map[anchor]}"'
+        return m.group(0)
+
+    def _replace_ac_anchor(m: re.Match[str]) -> str:
+        anchor = m.group(1)
+        if anchor in anchor_map:
+            return f'ac:anchor="{anchor_map[anchor]}"'
+        return m.group(0)
+
+    storage_body = re.sub(r'href="#([^"]+)"', _replace_href, storage_body)
+    storage_body = re.sub(r'ac:anchor="([^"]+)"', _replace_ac_anchor, storage_body)
+    return storage_body
+
+
+def rewrite_page_anchors(body: str, page_title: str) -> str:
+    """Rewrite markdown-style fragment anchors in *body* to Confluence-native format.
+
+    Returns *body* unchanged if no anchors need rewriting.
+    """
+    anchor_map = _build_anchor_map(body, page_title)
+    if not anchor_map:
+        return body
+    return _rewrite_anchors(body, anchor_map)
diff --git a/test_package/unit/test_anchor.py b/test_package/unit/test_anchor.py
new file mode 100644
index 0000000..73bf9c9
--- /dev/null
+++ b/test_package/unit/test_anchor.py
@@ -0,0 +1,197 @@
+from md2cf.anchor import (
+    _build_anchor_map,
+    _extract_headings,
+    _heading_to_markdown_anchor,
+    _rewrite_anchors,
+    _strip_for_anchor,
+    rewrite_page_anchors,
+)
+
+
+class TestStripForAnchor:
+    def test_removes_spaces(self):
+        assert _strip_for_anchor("The Concept") == "TheConcept"
+
+    def test_removes_hyphens(self):
+        assert (
+            _strip_for_anchor("SSH Reverse Tunnel - Guide") == "SSHReverseTunnelGuide"
+        )
+
+    def test_keeps_parentheses(self):
+        assert (
+            _strip_for_anchor("Disable Service (if needed)")
+            == "DisableService(ifneeded)"
+        )
+
+    def test_empty_string(self):
+        assert _strip_for_anchor("") == ""
+
+
+class TestHeadingToMarkdownAnchor:
+    def test_basic_heading(self):
+        assert _heading_to_markdown_anchor("The Concept") == "the-concept"
+
+    def test_strips_special_chars(self):
+        assert _heading_to_markdown_anchor("What's Next?") == "whats-next"
+
+    def test_multiple_spaces(self):
+        assert _heading_to_markdown_anchor("A   B   C") == "a-b-c"
+
+    def test_preserves_hyphens(self):
+        assert _heading_to_markdown_anchor("pre-existing") == "pre-existing"
+
+    def test_empty_string(self):
+        assert _heading_to_markdown_anchor("") == ""
+
+    def test_with_parentheses(self):
+        assert _heading_to_markdown_anchor("Setup (Optional)") == "setup-optional"
+
+
+class TestExtractHeadings:
+    def test_basic_headings(self):
+        body = "<h1>Introduction</h1><p>text</p><h2>Details</h2>"
+        assert _extract_headings(body) == ["Introduction", "Details"]
+
+    def test_strips_nested_tags(self):
+        body = "<h2><strong>Bold Heading</strong></h2>"
+        assert _extract_headings(body) == ["Bold Heading"]
+
+    def test_ignores_empty_headings(self):
+        body = "<h1></h1><h2>Real</h2>"
+        assert _extract_headings(body) == ["Real"]
+
+    def test_unescapes_html_entities(self):
+        body = "<h2>A &amp; B</h2>"
+        assert _extract_headings(body) == ["A & B"]
+
+    def test_no_headings(self):
+        assert _extract_headings("<p>just a paragraph</p>") == []
+
+    def test_heading_with_attributes(self):
+        body = '<h2 id="foo" class="bar">Heading</h2>'
+        assert _extract_headings(body) == ["Heading"]
+
+
+class TestBuildAnchorMap:
+    def test_basic_mapping(self):
+        body = "<h2>The Concept</h2>"
+        result = _build_anchor_map(body, "My Guide")
+        assert result == {"the-concept": "MyGuide-TheConcept"}
+
+    def test_duplicate_headings(self):
+        body = "<h2>Setup</h2><h2>Setup</h2><h2>Setup</h2>"
+        result = _build_anchor_map(body, "Page")
+        assert result == {
+            "setup": "Page-Setup",
+            "setup-1": "Page-Setup-1",
+            "setup-2": "Page-Setup-2",
+        }
+
+    def test_url_encodes_special_chars(self):
+        body = "<h2>Disable Service (if needed)</h2>"
+        result = _build_anchor_map(body, "Guide")
+        assert result == {
+            "disable-service-if-needed": "Guide-DisableService%28ifneeded%29",
+        }
+
+    def test_id_prefix_for_non_alpha_start(self):
+        body = "<h2>3rd Party Libraries</h2>"
+        result = _build_anchor_map(body, "")
+        # Title is empty so cf_anchor starts with "-" which is non-alpha
+        assert "3rd-party-libraries" in result
+        assert result["3rd-party-libraries"].startswith("id-")
+
+    def test_skips_when_md_equals_cf(self):
+        # Unlikely in practice but should not appear in map
+        body = "<h2>a</h2>"
+        result = _build_anchor_map(body, "")
+        # md_anchor = "a", cf_anchor = "-a" (starts with -), so id prefix is added
+        # They won't be equal in this case, but test the concept:
+        # If they were equal, they'd be skipped
+        for md, cf in result.items():
+            assert md != cf
+
+    def test_empty_body(self):
+        assert _build_anchor_map("", "Title") == {}
+
+    def test_long_title_with_hyphens(self):
+        body = "<h2>The Concept</h2>"
+        title = "SSH Reverse Tunnel Setup Guide" " - Embedded Hardware to AWS EC2"
+        result = _build_anchor_map(body, title)
+        expected_anchor = (
+            "SSHReverseTunnelSetupGuideEmbeddedHardwaretoAWSEC2" "-TheConcept"
+        )
+        assert result == {"the-concept": expected_anchor}
+
+
+class TestRewriteAnchors:
+    def test_rewrites_href(self):
+        body = '<a href="#the-concept">link</a>'
+        anchor_map = {"the-concept": "MyGuide-TheConcept"}
+        assert (
+            _rewrite_anchors(body, anchor_map)
+            == '<a href="#MyGuide-TheConcept">link</a>'
+        )
+
+    def test_rewrites_ac_anchor(self):
+        body = (
+            '<ac:link ac:anchor="the-concept">'
+            "<ac:link-body>text</ac:link-body></ac:link>"
+        )
+        anchor_map = {"the-concept": "MyGuide-TheConcept"}
+        result = _rewrite_anchors(body, anchor_map)
+        assert 'ac:anchor="MyGuide-TheConcept"' in result
+
+    def test_leaves_unknown_anchors(self):
+        body = '<a href="#unknown-heading">link</a>'
+        anchor_map = {"the-concept": "MyGuide-TheConcept"}
+        assert _rewrite_anchors(body, anchor_map) == body
+
+    def test_multiple_anchors(self):
+        body = '<a href="#one">1</a><a href="#two">2</a>'
+        anchor_map = {"one": "Page-One", "two": "Page-Two"}
+        result = _rewrite_anchors(body, anchor_map)
+        assert 'href="#Page-One"' in result
+        assert 'href="#Page-Two"' in result
+
+
+class TestRewritePageAnchors:
+    def test_end_to_end(self):
+        body = (
+            "<h1>Introduction</h1>"
+            '<p>See <a href="#the-concept">the concept</a>.</p>'
+            "<h2>The Concept</h2>"
+            "<p>Details here.</p>"
+            '<p>Back to <a href="#introduction">intro</a>.</p>'
+        )
+        result = rewrite_page_anchors(body, "My Guide")
+        assert 'href="#MyGuide-TheConcept"' in result
+        assert 'href="#MyGuide-Introduction"' in result
+
+    def test_no_headings_returns_unchanged(self):
+        body = '<p>No headings <a href="#foo">here</a>.</p>'
+        assert rewrite_page_anchors(body, "Title") == body
+
+    def test_no_fragment_links_returns_unchanged(self):
+        body = "<h2>Heading</h2><p>No links here.</p>"
+        # There are headings but no fragment links to rewrite, body is unchanged
+        result = rewrite_page_anchors(body, "Title")
+        assert result == body
+
+    def test_non_matching_fragment_left_untouched(self):
+        body = "<h2>Real Heading</h2>" '<p><a href="#nonexistent">link</a></p>'
+        result = rewrite_page_anchors(body, "Page")
+        # The #nonexistent anchor doesn't match any heading, left as-is
+        assert 'href="#nonexistent"' in result
+        # But the heading-matching anchors would be rewritten if referenced
+        assert (
+            'href="#Page-RealHeading"' not in result
+        )  # not referenced, so not in body
+
+    def test_with_prefix_in_title(self):
+        body = "<h2>Setup</h2>" '<a href="#setup">go</a>'
+        result = rewrite_page_anchors(body, "PREFIX - My Page")
+        assert 'href="#PREFIXMyPage-Setup"' in result
+
+    def test_empty_body(self):
+        assert rewrite_page_anchors("", "Title") == ""