diff --git a/org_mode_samples/object/plain_link/end_with_punctuation.org b/org_mode_samples/object/plain_link/end_with_punctuation.org
index 92df33d4..5a234913 100644
--- a/org_mode_samples/object/plain_link/end_with_punctuation.org
+++ b/org_mode_samples/object/plain_link/end_with_punctuation.org
@@ -1 +1,3 @@
 mailto:foo@bar.baz.
+
+mailto:foo@bar.baz....
diff --git a/src/parser/plain_link.rs b/src/parser/plain_link.rs
index 8518ae6c..387f788b 100644
--- a/src/parser/plain_link.rs
+++ b/src/parser/plain_link.rs
@@ -134,6 +134,7 @@ fn path_plain<'r, 's>(
         many_till(anychar, peek(exit_matcher)),
         |(children, _exit_contents)| !children.is_empty(),
     ))(input)?;
+
     Ok((remaining, path))
 }
 
@@ -142,5 +143,10 @@ fn path_plain_end<'r, 's>(
     _context: Context<'r, 's>,
     input: OrgSource<'s>,
 ) -> Res<OrgSource<'s>, OrgSource<'s>> {
-    recognize(one_of(" \t\r\n()[]<>"))(input)
+    recognize(many_till(
+        verify(anychar, |c| {
+            *c != '/' && (c.is_ascii_punctuation() || c.is_whitespace())
+        }),
+        one_of(" \t\r\n()[]<>"),
+    ))(input)
 }