diff --git a/devplacepy/rendering.py b/devplacepy/rendering.py
index daf055bb..753bf3ba 100644
--- a/devplacepy/rendering.py
+++ b/devplacepy/rendering.py
@@ -79,6 +79,7 @@ _EMAIL_RE = re.compile(r"\b[A-Za-z0-9._%+\-]+@[A-Za-z0-9.\-]+\.[A-Za-z]{2,}\b")
 _EMAIL_KEEP_DOMAIN = "molodetz.nl"
 
 _MEDIA_SKIP_TAGS = {"a", "code", "pre"}
+_TRAILING_PUNCT_RE = re.compile(r"[.,;:!?)\]}\"']+$")
 _TITLE_INLINE_TAGS = {
     "b", "strong", "i", "em", "code", "del", "s", "mark", "sub", "sup", "span", "br",
 }
@@ -139,6 +140,11 @@ def _alt_from_url(url: str) -> str:
 
 
 def _embed_url(url: str) -> str:
+    trail = ""
+    punct_match = _TRAILING_PUNCT_RE.search(url)
+    if punct_match:
+        trail = punct_match.group()
+        url = url[: punct_match.start()]
     youtube = _YOUTUBE_RE.search(url)
     if youtube:
         video_id = youtube.group(1)
@@ -146,19 +152,19 @@ def _embed_url(url: str) -> str:
             f'<div class="embed-youtube"><iframe '
             f'src="https://www.youtube.com/embed/{video_id}" '
             f'frameborder="0" allowfullscreen allow="{_YOUTUBE_ALLOW}">'
-            f"</iframe></div>"
+            f"</iframe></div>{trail}"
         )
     escaped = html.escape(url, quote=True)
     if _IMAGE_RE.search(url):
         alt = html.escape(_alt_from_url(url), quote=True)
-        return f'<img src="{escaped}" alt="{alt}" loading="lazy" data-lightbox>'
+        return f'<img src="{escaped}" alt="{alt}" loading="lazy" data-lightbox>{trail}'
     if _VIDEO_RE.search(url):
-        return f'<video src="{escaped}" controls preload="metadata"></video>'
+        return f'<video src="{escaped}" controls preload="metadata"></video>{trail}'
     if _AUDIO_RE.search(url):
-        return f'<audio src="{escaped}" controls preload="metadata"></audio>'
+        return f'<audio src="{escaped}" controls preload="metadata"></audio>{trail}'
     return (
         f'<a href="{escaped}" target="_blank" rel="noopener noreferrer">'
-        f"{html.escape(url)}</a>"
+        f"{html.escape(url)}</a>{trail}"
     )
 
 
diff --git a/devplacepy/static/js/ContentRenderer.js b/devplacepy/static/js/ContentRenderer.js
index 67282015..1a4eca35 100644
--- a/devplacepy/static/js/ContentRenderer.js
+++ b/devplacepy/static/js/ContentRenderer.js
@@ -188,17 +188,21 @@ export class ContentRenderer {
                     a.textContent = "@" + part.username;
                     fragment.appendChild(a);
                 } else {
-                    const el = this.urlToEmbed(part.value);
+                    const { cleaned, trail } = this.stripTrailingPunct(part.value);
+                    const el = this.urlToEmbed(cleaned);
                     if (el) {
                         fragment.appendChild(el);
                     } else {
                         const a = document.createElement("a");
-                        a.href = part.value;
+                        a.href = cleaned;
                         a.target = "_blank";
                         a.rel = "noopener noreferrer";
-                        a.textContent = part.value;
+                        a.textContent = cleaned;
                         fragment.appendChild(a);
                     }
+                    if (trail) {
+                        fragment.appendChild(document.createTextNode(trail));
+                    }
                 }
             }
 
@@ -282,6 +286,14 @@ export class ContentRenderer {
         return null;
     }
 
+    stripTrailingPunct(url) {
+        const m = url.match(/[.,;:!?)\]}\"']+$/);
+        if (m) {
+            return { cleaned: url.slice(0, m.index), trail: m[0] };
+        }
+        return { cleaned: url, trail: "" };
+    }
+
     walkNodes(root, callback) {
         const skipTags = new Set(["CODE", "PRE", "A", "IFRAME", "IMG", "VIDEO", "SCRIPT", "STYLE"]);
         const iter = document.createNodeIterator(root, NodeFilter.SHOW_TEXT, null, false);
diff --git a/tests/unit/rendering.py b/tests/unit/rendering.py
index d5ba187b..a4c1d06c 100644
--- a/tests/unit/rendering.py
+++ b/tests/unit/rendering.py
@@ -263,3 +263,46 @@ def test_xss_legitimate_link_survives_audit():
     out = str(render_content("see https://example.com/page ok"))
     assert 'href="https://example.com/page"' in out
     assert_no_executable_html(out)
+
+
+def test_bare_url_with_trailing_period():
+    out = str(render_content("see https://example.com/page."))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>." in out
+    assert "https://example.com/page.</a>" not in out
+
+
+def test_bare_url_with_trailing_comma():
+    out = str(render_content("check https://example.com/page,"))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>," in out
+
+
+def test_bare_url_with_trailing_exclamation():
+    out = str(render_content("look https://example.com/page!"))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>!" in out
+
+
+def test_bare_url_with_trailing_question_mark():
+    out = str(render_content("did you see https://example.com/page?"))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>?" in out
+
+
+def test_bare_url_with_trailing_paren():
+    out = str(render_content("see (https://example.com/page)"))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>)" in out
+
+
+def test_bare_url_with_trailing_multiple_punctuation():
+    out = str(render_content("visit https://example.com/page..."))
+    assert 'href="https://example.com/page"' in out
+    assert "</a>..." in out
+
+
+def test_bare_url_without_trailing_punctuation_unchanged():
+    out = str(render_content("see https://example.com/page ok"))
+    assert 'href="https://example.com/page"' in out
+    assert "https://example.com/page</a> " in out