diff --git a/src/librustdoc/html/escape.rs b/src/librustdoc/html/escape.rs
index 3e20c5b322b..f8199cd6e0e 100644
--- a/src/librustdoc/html/escape.rs
+++ b/src/librustdoc/html/escape.rs
@@ -107,12 +107,17 @@ impl<'a> fmt::Display for EscapeBodyTextWithWbr<'a> {
             let next_is_uppercase =
                 || pk.map_or(true, |(_, t)| t.chars().any(|c| c.is_uppercase()));
             let next_is_underscore = || pk.map_or(true, |(_, t)| t.contains('_'));
+            let next_is_colon = || pk.map_or(true, |(_, t)| t.contains(':'));
             if (i - last > 3 && is_uppercase() && !next_is_uppercase())
                 || (s.contains('_') && !next_is_underscore())
             {
                 EscapeBodyText(&text[last..i]).fmt(fmt)?;
                 fmt.write_str("<wbr>")?;
                 last = i;
+            } else if s.contains(':') && !next_is_colon() {
+                EscapeBodyText(&text[last..i + 1]).fmt(fmt)?;
+                fmt.write_str("<wbr>")?;
+                last = i + 1;
             }
         }
         if last < text.len() {
diff --git a/src/librustdoc/html/escape/tests.rs b/src/librustdoc/html/escape/tests.rs
index 7933f23eb74..e2d81cf5c27 100644
--- a/src/librustdoc/html/escape/tests.rs
+++ b/src/librustdoc/html/escape/tests.rs
@@ -6,6 +6,12 @@ fn escape_body_text_with_wbr() {
     assert_eq!(&E("").to_string(), "");
     assert_eq!(&E("a").to_string(), "a");
     assert_eq!(&E("A").to_string(), "A");
+    assert_eq!(&E("_").to_string(), "_");
+    assert_eq!(&E(":").to_string(), ":");
+    assert_eq!(&E(" ").to_string(), " ");
+    assert_eq!(&E("___________").to_string(), "___________");
+    assert_eq!(&E(":::::::::::").to_string(), ":::::::::::");
+    assert_eq!(&E("           ").to_string(), "           ");
     // real(istic) examples
     assert_eq!(&E("FirstSecond").to_string(), "First<wbr>Second");
     assert_eq!(&E("First_Second").to_string(), "First<wbr>_Second");
@@ -15,8 +21,9 @@ fn escape_body_text_with_wbr() {
     assert_eq!(&E("First SecondThird").to_string(), "First Second<wbr>Third");
     assert_eq!(&E("First<T>_Second").to_string(), "First&lt;<wbr>T&gt;<wbr>_Second");
     assert_eq!(&E("first_second").to_string(), "first<wbr>_second");
+    assert_eq!(&E("first:second").to_string(), "first:<wbr>second");
+    assert_eq!(&E("first::second").to_string(), "first::<wbr>second");
     assert_eq!(&E("MY_CONSTANT").to_string(), "MY<wbr>_CONSTANT");
-    assert_eq!(&E("___________").to_string(), "___________");
     // a string won't get wrapped if it's less than 8 bytes
     assert_eq!(&E("HashSet").to_string(), "HashSet");
     // an individual word won't get wrapped if it's less than 4 bytes
diff --git a/src/librustdoc/html/render/print_item.rs b/src/librustdoc/html/render/print_item.rs
index 3f01c082ba9..eec6df9dd20 100644
--- a/src/librustdoc/html/render/print_item.rs
+++ b/src/librustdoc/html/render/print_item.rs
@@ -558,7 +558,7 @@ fn extra_info_tags<'a, 'tcx: 'a>(
             display_fn(move |f| {
                 write!(
                     f,
-                    r#"<span class="stab {class}" title="{title}">{contents}</span>"#,
+                    r#"<wbr><span class="stab {class}" title="{title}">{contents}</span>"#,
                     title = Escape(title),
                 )
             })
diff --git a/src/librustdoc/html/static/css/rustdoc.css b/src/librustdoc/html/static/css/rustdoc.css
index e936e1ca07e..cafe5fe4c87 100644
--- a/src/librustdoc/html/static/css/rustdoc.css
+++ b/src/librustdoc/html/static/css/rustdoc.css
@@ -586,12 +586,15 @@ ul.block, .block li {
 }
 
 .sidebar h2 {
+	text-wrap: balance;
 	overflow-wrap: anywhere;
 	padding: 0;
 	margin: 0.7rem 0;
 }
 
 .sidebar h3 {
+	text-wrap: balance;
+	overflow-wrap: anywhere;
 	font-size: 1.125rem; /* 18px */
 	padding: 0;
 	margin: 0;
@@ -2222,7 +2225,7 @@ in src-script.js and main.js
 		width: 33%;
 	}
 	.item-table > li > div {
-		word-break: break-all;
+		overflow-wrap: anywhere;
 	}
 }
 
diff --git a/src/librustdoc/html/templates/sidebar.html b/src/librustdoc/html/templates/sidebar.html
index 025220ab415..0990c2716b8 100644
--- a/src/librustdoc/html/templates/sidebar.html
+++ b/src/librustdoc/html/templates/sidebar.html
@@ -31,6 +31,6 @@
         </section>
     {% endif %}
     {% if !path.is_empty() %}
-        <h2><a href="{% if is_mod %}../{% endif %}index.html">In {{+ path}}</a></h2>
+        <h2><a href="{% if is_mod %}../{% endif %}index.html">In {{+ path|wrapped|safe}}</a></h2>
     {% endif %}
 </div>
diff --git a/tests/rustdoc-gui/label-next-to-symbol.goml b/tests/rustdoc-gui/label-next-to-symbol.goml
index 1fa0a120ada..a8363f29dd5 100644
--- a/tests/rustdoc-gui/label-next-to-symbol.goml
+++ b/tests/rustdoc-gui/label-next-to-symbol.goml
@@ -27,7 +27,8 @@ compare-elements-position-near: (
     ".item-name .stab.deprecated",
     {"y": 2},
 )
-compare-elements-position: (
+// "Unix" part is on second line
+compare-elements-position-false: (
     ".item-name .stab.deprecated",
     ".item-name .stab.portability",
     ["y"],