diff --git a/decnet/canary/factory.py b/decnet/canary/factory.py
index bc641eb0..876906e0 100644
--- a/decnet/canary/factory.py
+++ b/decnet/canary/factory.py
@@ -18,6 +18,8 @@ KNOWN_GENERATORS: Tuple[str, ...] = (
     "ssh_key",
     "aws_creds",
     "honeydoc",
+    "honeydoc_docx",
+    "honeydoc_pdf",
 )
 
 KNOWN_INSTRUMENTERS: Tuple[str, ...] = (
@@ -52,6 +54,12 @@ def get_generator(name: str) -> CanaryGenerator:
     if name == "honeydoc":
         from decnet.canary.generators.honeydoc import HoneydocGenerator
         return HoneydocGenerator()
+    if name == "honeydoc_docx":
+        from decnet.canary.generators.honeydoc_docx import HoneydocDocxGenerator
+        return HoneydocDocxGenerator()
+    if name == "honeydoc_pdf":
+        from decnet.canary.generators.honeydoc_pdf import HoneydocPdfGenerator
+        return HoneydocPdfGenerator()
     raise ValueError(
         f"Unknown canary generator: {name!r}. Known: {KNOWN_GENERATORS}"
     )
diff --git a/decnet/canary/generators/honeydoc_docx.py b/decnet/canary/generators/honeydoc_docx.py
new file mode 100644
index 00000000..35456a23
--- /dev/null
+++ b/decnet/canary/generators/honeydoc_docx.py
@@ -0,0 +1,133 @@
+"""Real-DOCX honeydoc generator.
+
+Synthesises a minimal but structurally valid DOCX from scratch via
+stdlib :mod:`zipfile`, then uses the same external-image relationship
+trick that powers :mod:`decnet.canary.instrumenters.docx` to embed
+the callback URL.  No python-docx dependency.
+
+The output opens cleanly in Word / LibreOffice; both fetch the
+external image relationship on document load.
+"""
+from __future__ import annotations
+
+import io
+import zipfile
+
+from decnet.canary.base import CanaryArtifact, CanaryContext, CanaryGenerator
+from decnet.canary.instrumenters.docx import _drawing, _next_rid
+
+
+_CONTENT_TYPES = (
+    '<?xml version="1.0" encoding="UTF-8" standalone="yes"?>'
+    '<Types xmlns="http://schemas.openxmlformats.org/package/2006/content-types">'
+    '<Default Extension="xml" ContentType="application/xml"/>'
+    '<Default Extension="rels" ContentType="application/vnd.openxmlformats-package.relationships+xml"/>'
+    '<Override PartName="/word/document.xml" '
+    'ContentType="application/vnd.openxmlformats-officedocument.wordprocessingml.document.main+xml"/>'
+    '</Types>'
+).encode()
+
+_PACKAGE_RELS = (
+    '<?xml version="1.0" encoding="UTF-8" standalone="yes"?>'
+    '<Relationships xmlns="http://schemas.openxmlformats.org/package/2006/relationships">'
+    '<Relationship Id="rId1" '
+    'Type="http://schemas.openxmlformats.org/officeDocument/2006/relationships/officeDocument" '
+    'Target="word/document.xml"/>'
+    '</Relationships>'
+).encode()
+
+_BODY_PARAGRAPHS = (
+    "Q3 Operations Review (DRAFT — DO NOT DISTRIBUTE)",
+    "",
+    "Forecast and remediation timeline below. Numbers are preliminary "
+    "and subject to revision before the all-hands.",
+    "",
+    "Region        Incidents     MTTR (h)",
+    "us-east       14            3.2",
+    "us-west       9             4.7",
+    "eu-central    22            2.1",
+    "",
+    "Internal contact: secops@internal",
+)
+
+
+def _document_xml(rid_with_drawing: str | None = None) -> bytes:
+    """Build the body XML.
+
+    ``rid_with_drawing`` is the rId of the external image relationship;
+    when set, we append the same ``<w:drawing>`` element that the DOCX
+    instrumenter inserts so the body references the external resource.
+    """
+    paragraphs = []
+    for line in _BODY_PARAGRAPHS:
+        if line:
+            paragraphs.append(
+                "<w:p><w:r><w:t xml:space=\"preserve\">"
+                + _xml_escape(line)
+                + "</w:t></w:r></w:p>"
+            )
+        else:
+            paragraphs.append("<w:p/>")
+    body = "".join(paragraphs)
+    drawing = _drawing(rid_with_drawing).decode() if rid_with_drawing else ""
+    return (
+        '<?xml version="1.0" encoding="UTF-8" standalone="yes"?>'
+        '<w:document xmlns:w="http://schemas.openxmlformats.org/wordprocessingml/2006/main">'
+        f'<w:body>{body}{drawing}</w:body>'
+        '</w:document>'
+    ).encode()
+
+
+def _xml_escape(s: str) -> str:
+    return (
+        s.replace("&", "&amp;")
+         .replace("<", "&lt;")
+         .replace(">", "&gt;")
+    )
+
+
+def _document_rels(rid: str, url: str) -> bytes:
+    return (
+        '<?xml version="1.0" encoding="UTF-8" standalone="yes"?>'
+        '<Relationships xmlns="http://schemas.openxmlformats.org/package/2006/relationships">'
+        f'<Relationship Id="{rid}" '
+        f'Type="http://schemas.openxmlformats.org/officeDocument/2006/relationships/image" '
+        f'Target="{url}" TargetMode="External"/>'
+        '</Relationships>'
+    ).encode()
+
+
+class HoneydocDocxGenerator(CanaryGenerator):
+    name = "honeydoc_docx"
+
+    def generate(self, ctx: CanaryContext) -> CanaryArtifact:
+        url = f"{ctx.http_base.rstrip('/')}/c/{ctx.callback_token}"
+        # Pick a stable rId — there's only one relationship in the
+        # synthesised file, so any unused id works.  Reuse the
+        # instrumenter's allocator against the bare relationships
+        # skeleton for parity with operator-uploaded DOCX flow.
+        skeleton = (
+            b'<?xml version="1.0" encoding="UTF-8" standalone="yes"?>'
+            b'<Relationships xmlns="http://schemas.openxmlformats.org/package/2006/relationships">'
+            b'</Relationships>'
+        )
+        rid = _next_rid(skeleton)
+
+        out = io.BytesIO()
+        with zipfile.ZipFile(out, "w", zipfile.ZIP_DEFLATED) as zf:
+            zf.writestr("[Content_Types].xml", _CONTENT_TYPES)
+            zf.writestr("_rels/.rels", _PACKAGE_RELS)
+            zf.writestr("word/document.xml", _document_xml(rid))
+            zf.writestr("word/_rels/document.xml.rels", _document_rels(rid, url))
+
+        return CanaryArtifact(
+            path="",
+            content=out.getvalue(),
+            mode=0o644,
+            mtime_offset=-86400 * 21,
+            generator=self.name,
+            notes=[
+                "synthesised DOCX with realistic Q3 review body",
+                f"external-image relationship {rid} -> {url}",
+            ],
+        )
diff --git a/decnet/canary/generators/honeydoc_pdf.py b/decnet/canary/generators/honeydoc_pdf.py
new file mode 100644
index 00000000..400271ff
--- /dev/null
+++ b/decnet/canary/generators/honeydoc_pdf.py
@@ -0,0 +1,127 @@
+"""Real-PDF honeydoc generator (uses :mod:`pikepdf`).
+
+Builds a one-page PDF with the same Q3-review body as the HTML/DOCX
+flavors and installs an ``/OpenAction`` ``/URI`` action on the
+catalog so most viewers fire the callback the moment the document
+opens.
+
+Pikepdf is now a hard dependency for this generator (the operator
+installed it explicitly so we can use it).  We still surface a
+clear :class:`InstrumenterRejectedError` when imports fail, so a
+deployment without pikepdf can fall back to the DOCX or HTML
+generators rather than crashing the API.
+"""
+from __future__ import annotations
+
+import io
+
+from decnet.canary.base import (
+    CanaryArtifact,
+    CanaryContext,
+    CanaryGenerator,
+    InstrumenterRejectedError,
+)
+
+
+_BODY_LINES = (
+    ("Q3 Operations Review (DRAFT — DO NOT DISTRIBUTE)", 14),
+    ("", 12),
+    ("Forecast and remediation timeline below.", 11),
+    ("Numbers are preliminary, subject to revision.", 11),
+    ("", 12),
+    ("Region        Incidents     MTTR (h)", 11),
+    ("us-east       14            3.2", 11),
+    ("us-west       9             4.7",  11),
+    ("eu-central    22            2.1",  11),
+    ("", 12),
+    ("Internal contact: secops@internal", 11),
+)
+
+
+class HoneydocPdfGenerator(CanaryGenerator):
+    name = "honeydoc_pdf"
+
+    def generate(self, ctx: CanaryContext) -> CanaryArtifact:
+        try:
+            from pikepdf import Pdf, Name, Dictionary, String  # type: ignore[import-not-found]
+        except ImportError as e:
+            raise InstrumenterRejectedError(
+                "honeydoc_pdf requires pikepdf; install it (`pip install "
+                "pikepdf`) or pick honeydoc / honeydoc_docx instead."
+            ) from e
+
+        url = f"{ctx.http_base.rstrip('/')}/c/{ctx.callback_token}"
+
+        pdf = Pdf.new()
+        # Helvetica is one of the 14 PDF base fonts — every viewer ships
+        # it, so no font embedding is required.
+        font = pdf.make_indirect(Dictionary(
+            Type=Name("/Font"),
+            Subtype=Name("/Type1"),
+            BaseFont=Name("/Helvetica"),
+        ))
+
+        # Build a single content stream that writes each body line at a
+        # decreasing y-coordinate.  PDF coordinates start at the bottom-
+        # left (US Letter = 612 x 792 points); we lay out lines roughly
+        # 18 points apart starting near the top.
+        ops: list[str] = ["BT /F1 12 Tf 72 750 Td"]
+        first = True
+        for line, size in _BODY_LINES:
+            if not first:
+                ops.append("0 -18 Td")
+            first = False
+            ops.append(f"/F1 {size} Tf")
+            ops.append(f"({_pdf_escape(line)}) Tj")
+        ops.append("ET")
+        content_bytes = "\n".join(ops).encode("latin-1")
+
+        content_stream = pdf.make_stream(content_bytes)
+
+        page = pdf.add_blank_page(page_size=(612, 792))
+        page[Name("/Resources")] = Dictionary(
+            Font=Dictionary(F1=font),
+        )
+        page[Name("/Contents")] = content_stream
+
+        # OpenAction fires the URI when the file is opened in Acrobat,
+        # Preview, the browser PDF viewer, etc.  Most viewers prompt
+        # before fetching; that prompt itself is a tell, and an
+        # auto-allow viewer fetches silently.
+        pdf.Root[Name("/OpenAction")] = Dictionary(
+            Type=Name("/Action"),
+            S=Name("/URI"),
+            URI=String(url),
+        )
+
+        out = io.BytesIO()
+        pdf.save(out)
+        return CanaryArtifact(
+            path="",
+            content=out.getvalue(),
+            mode=0o644,
+            mtime_offset=-86400 * 21,
+            generator=self.name,
+            notes=[
+                "synthesised one-page PDF with realistic Q3 review body",
+                f"/OpenAction /URI -> {url}",
+            ],
+        )
+
+
+def _pdf_escape(s: str) -> str:
+    """Escape parens and backslashes for PDF literal-string syntax.
+
+    PDF string literals are wrapped in ``( … )``; inner ``(``, ``)``,
+    and ``\\`` need backslash escapes.  Everything else (including
+    UTF-8 multibyte sequences) round-trips fine because Helvetica's
+    encoding is WinAnsi-ish — we'll lose exotic glyphs but the
+    realistic body sticks to ASCII anyway.  Em-dashes are downgraded
+    to ``--`` to avoid the WinAnsi gap.
+    """
+    return (
+        s.replace("\\", r"\\")
+         .replace("(", r"\(")
+         .replace(")", r"\)")
+         .replace("—", "--")
+    )
diff --git a/decnet/canary/paths.py b/decnet/canary/paths.py
index 35c84c50..5700ad0f 100644
--- a/decnet/canary/paths.py
+++ b/decnet/canary/paths.py
@@ -25,7 +25,9 @@ _LINUX_DEFAULTS: dict[str, str] = {
     "env_file": "/home/{user}/.env",
     "ssh_key": "/home/{user}/.ssh/id_rsa",
     "aws_creds": "/home/{user}/.aws/credentials",
-    "honeydoc": "/home/{user}/Documents/quarterly_report.docx",
+    "honeydoc": "/home/{user}/Documents/quarterly_report.html",
+    "honeydoc_docx": "/home/{user}/Documents/quarterly_report.docx",
+    "honeydoc_pdf": "/home/{user}/Documents/quarterly_report.pdf",
 }
 
 _WINDOWS_DEFAULTS: dict[str, str] = {
@@ -33,7 +35,9 @@ _WINDOWS_DEFAULTS: dict[str, str] = {
     "env_file": "/home/{user}/Desktop/prod.env",
     "ssh_key": "/home/{user}/.ssh/id_rsa",  # OpenSSH on Windows uses the same path
     "aws_creds": "/home/{user}/.aws/credentials",
-    "honeydoc": "/home/{user}/Documents/quarterly_report.docx",
+    "honeydoc": "/home/{user}/Documents/quarterly_report.html",
+    "honeydoc_docx": "/home/{user}/Documents/quarterly_report.docx",
+    "honeydoc_pdf": "/home/{user}/Documents/quarterly_report.pdf",
 }
 
 
diff --git a/decnet_web/src/components/CanaryTokens.tsx b/decnet_web/src/components/CanaryTokens.tsx
index fe06b5d2..83f3e5bc 100644
--- a/decnet_web/src/components/CanaryTokens.tsx
+++ b/decnet_web/src/components/CanaryTokens.tsx
@@ -20,7 +20,8 @@ interface BlobRow {
 }
 
 const KNOWN_GENERATORS = [
-  'git_config', 'env_file', 'ssh_key', 'aws_creds', 'honeydoc',
+  'git_config', 'env_file', 'ssh_key', 'aws_creds',
+  'honeydoc', 'honeydoc_docx', 'honeydoc_pdf',
 ] as const;
 type GeneratorName = typeof KNOWN_GENERATORS[number];
 
diff --git a/tests/canary/test_factory.py b/tests/canary/test_factory.py
index ecb85985..e7db4390 100644
--- a/tests/canary/test_factory.py
+++ b/tests/canary/test_factory.py
@@ -59,7 +59,8 @@ def test_known_lists_are_stable() -> None:
     # If anyone adds/removes from the dispatch tables, the test
     # surfaces it. Keeps the schema-of-record in one place.
     assert KNOWN_GENERATORS == (
-        "git_config", "env_file", "ssh_key", "aws_creds", "honeydoc",
+        "git_config", "env_file", "ssh_key", "aws_creds",
+        "honeydoc", "honeydoc_docx", "honeydoc_pdf",
     )
     assert KNOWN_INSTRUMENTERS == (
         "docx", "xlsx", "pdf", "html", "image", "plain", "passthrough",
diff --git a/tests/canary/test_generators.py b/tests/canary/test_generators.py
index e80566a5..0127b3a4 100644
--- a/tests/canary/test_generators.py
+++ b/tests/canary/test_generators.py
@@ -90,6 +90,37 @@ def test_honeydoc_html_is_valid_ish_html() -> None:
     assert "width=\"1\" height=\"1\"" in body
 
 
+def test_honeydoc_docx_produces_valid_zip_with_callback() -> None:
+    import io
+    import zipfile
+    g = get_generator("honeydoc_docx")
+    art = g.generate(_ctx(callback_token="slugDX"))
+    assert art.content[:4] == b"PK\x03\x04"  # zip magic
+    with zipfile.ZipFile(io.BytesIO(art.content), "r") as zf:
+        names = set(zf.namelist())
+        assert {"[Content_Types].xml", "_rels/.rels", "word/document.xml",
+                "word/_rels/document.xml.rels"} <= names
+        rels = zf.read("word/_rels/document.xml.rels").decode()
+        assert "https://canary.example.test/c/slugDX" in rels
+        assert "TargetMode=\"External\"" in rels
+        doc = zf.read("word/document.xml").decode()
+        assert "Q3 Operations Review" in doc
+        assert "<w:drawing>" in doc
+
+
+def test_honeydoc_pdf_produces_valid_pdf_with_openaction() -> None:
+    pikepdf = pytest.importorskip("pikepdf")
+    g = get_generator("honeydoc_pdf")
+    art = g.generate(_ctx(callback_token="slugPDF"))
+    assert art.content[:5] == b"%PDF-"
+    # Re-open and confirm OpenAction URI round-trips.
+    import io
+    with pikepdf.open(io.BytesIO(art.content)) as pdf:
+        action = pdf.Root["/OpenAction"]
+        assert str(action["/S"]) == "/URI"
+        assert str(action["/URI"]) == "https://canary.example.test/c/slugPDF"
+
+
 def test_git_config_remote_url_shape() -> None:
     g = get_generator("git_config")
     art = g.generate(_ctx(callback_token="slug42"))
diff --git a/tests/canary/test_paths.py b/tests/canary/test_paths.py
index c633d4f5..65232fe2 100644
--- a/tests/canary/test_paths.py
+++ b/tests/canary/test_paths.py
@@ -28,7 +28,9 @@ def test_default_user_dispatch() -> None:
         ("env_file", "windows", "/home/Administrator/Desktop/prod.env"),
         ("git_config", "linux", "/home/admin/.git/config"),
         ("ssh_key", "linux", "/home/admin/.ssh/id_rsa"),
-        ("honeydoc", "linux", "/home/admin/Documents/quarterly_report.docx"),
+        ("honeydoc", "linux", "/home/admin/Documents/quarterly_report.html"),
+        ("honeydoc_docx", "linux", "/home/admin/Documents/quarterly_report.docx"),
+        ("honeydoc_pdf", "linux", "/home/admin/Documents/quarterly_report.pdf"),
     ],
 )
 def test_default_path_for_known_generators(