diff --git a/archivebox/misc/serve_static.py b/archivebox/misc/serve_static.py
index 9e36e77d..6068722f 100644
--- a/archivebox/misc/serve_static.py
+++ b/archivebox/misc/serve_static.py
@@ -32,6 +32,19 @@ from archivebox.misc.logging_util import printable_filesize
 
 _HASHES_CACHE: dict[Path, tuple[float, dict[str, str]]] = {}
 IMG_SRC_ATTR_RE = re.compile(r'(<img\b[^>]*?\s(?:src|data-src)=["\'])([^"\']+)(["\'])', re.IGNORECASE)
+TRANSFORMED_HTML_PREVIEW_STYLE = """<style id="archivebox-static-html-preview-style">
+img:not([width]):not([height]) {
+    max-width: min(100%, 12rem);
+    max-height: 12rem;
+    width: auto;
+    height: auto;
+    object-fit: contain;
+}
+a > img:not([width]):not([height]) {
+    max-width: min(100%, 2.5rem);
+    max-height: 2.5rem;
+}
+</style>"""
 
 
 def _load_hash_map(snapshot_dir: Path) -> dict[str, str] | None:
@@ -531,6 +544,14 @@ def _rewrite_html_image_sources_for_request(
     )
 
 
+def _apply_transformed_html_preview_style(html_text: str) -> str:
+    if "archivebox-static-html-preview-style" in html_text:
+        return html_text
+    if re.search(r"</head\s*>", html_text, flags=re.IGNORECASE):
+        return re.sub(r"</head\s*>", f"{TRANSFORMED_HTML_PREVIEW_STYLE}\\g<0>", html_text, count=1, flags=re.IGNORECASE)
+    return f"{TRANSFORMED_HTML_PREVIEW_STYLE}\n{html_text}"
+
+
 def _set_transformed_response_headers(response, fullpath: Path, statobj: os.stat_result, encoding: str | None, config) -> None:
     response.headers["Last-Modified"] = http_date(statobj.st_mtime)
     response.headers["Cache-Control"] = f"{_cache_policy(config=config)}, max-age=60, stale-while-revalidate=300"
@@ -963,6 +984,7 @@ def serve_static_with_byterange_support(request, path, document_root=None, show_
                 if _looks_like_markdown(markdown_candidate):
                     wrapped = _render_markdown_document(markdown_candidate)
                     wrapped, _rewrite_count = _rewrite_html_image_sources_for_request(request, wrapped, document_root, rel_path)
+                    wrapped = _apply_transformed_html_preview_style(wrapped)
                     response = HttpResponse(wrapped, content_type="text/html; charset=utf-8")
                     _set_transformed_response_headers(response, fullpath, statobj, encoding, config)
                     return _apply_archive_replay_headers(
@@ -973,6 +995,7 @@ def serve_static_with_byterange_support(request, path, document_root=None, show_
                         config=config,
                     )
                 if rewritten_count:
+                    rewritten_html = _apply_transformed_html_preview_style(rewritten_html)
                     response = HttpResponse(rewritten_html, content_type=content_type)
                     _set_transformed_response_headers(response, fullpath, statobj, encoding, config)
                     return _apply_archive_replay_headers(
@@ -983,6 +1006,7 @@ def serve_static_with_byterange_support(request, path, document_root=None, show_
                         config=config,
                     )
                 if escaped_count and escaped_count > tag_count * 2:
+                    decoded = _apply_transformed_html_preview_style(decoded)
                     response = HttpResponse(decoded, content_type=content_type)
                     _set_transformed_response_headers(response, fullpath, statobj, encoding, config)
                     return _apply_archive_replay_headers(
diff --git a/archivebox/tests/test_urls.py b/archivebox/tests/test_urls.py
index 316107ef..3f2c2d36 100644
--- a/archivebox/tests/test_urls.py
+++ b/archivebox/tests/test_urls.py
@@ -57,7 +57,7 @@ def test_static_html_and_markdown_preview_images_rewrite_to_captured_responses(t
 
     html_path = tmp_path / "extractor" / "content.html"
     html_path.parent.mkdir()
-    html_path.write_text('<img src="images/twitter.png">', encoding="utf-8")
+    html_path.write_text('<img src="images/twitter.png"><img width="48" src="images/twitter.png">', encoding="utf-8")
 
     request = RequestFactory().get("/web/20260722/sweeting.me/snapshot/extractor/content.html")
     request.archivebox_snapshot_url = "https://sweeting.me/"
@@ -67,7 +67,14 @@ def test_static_html_and_markdown_preview_images_rewrite_to_captured_responses(t
     assert response.status_code == 200
     assert "ETag" not in response.headers
     assert "max-age=60" in response.headers["Cache-Control"]
+    assert b"archivebox-static-html-preview-style" in response.content
+    assert b"img:not([width]):not([height])" in response.content
+    assert b"a > img:not([width]):not([height])" in response.content
     assert b'src="../responses/all/20260722T061544__GET__https_3A_2F_2Fsweeting.me_2Fimages_2Ftwitter.png"' in response.content
+    assert (
+        b'<img width="48" src="../responses/all/20260722T061544__GET__https_3A_2F_2Fsweeting.me_2Fimages_2Ftwitter.png">'
+        in response.content
+    )
 
     text_path = tmp_path / "article" / "content.txt"
     text_path.parent.mkdir()
@@ -89,6 +96,7 @@ def test_static_html_and_markdown_preview_images_rewrite_to_captured_responses(t
     assert response.status_code == 200
     assert "ETag" not in response.headers
     assert "max-age=60" in response.headers["Cache-Control"]
+    assert b"archivebox-static-html-preview-style" in response.content
     assert b'src="../responses/all/20260722T061544__GET__https_3A_2F_2Fsweeting.me_2Fimages_2Ftwitter.png"' in response.content