diff --git a/org_mode_samples/greater_element/plain_list/description_eof.org b/org_mode_samples/greater_element/plain_list/description_eof.org
new file mode 100644
index 0000000..0f72e5d
--- /dev/null
+++ b/org_mode_samples/greater_element/plain_list/description_eof.org
@@ -0,0 +1,2 @@
+- foo ::
+
diff --git a/org_mode_samples/greater_element/plain_list/description_list.org b/org_mode_samples/greater_element/plain_list/description_list.org
index ef014f7..5bbcedf 100644
--- a/org_mode_samples/greater_element/plain_list/description_list.org
+++ b/org_mode_samples/greater_element/plain_list/description_list.org
@@ -6,3 +6,6 @@
 -
   lorem :: ipsum
 - dolar *bold* foo :: ipsum
+- big gap ::
+
+  stuff
diff --git a/src/parser/plain_list.rs b/src/parser/plain_list.rs
index 8386796..75bdbd0 100644
--- a/src/parser/plain_list.rs
+++ b/src/parser/plain_list.rs
@@ -6,9 +6,12 @@ use nom::character::complete::one_of;
 use nom::character::complete::space0;
 use nom::character::complete::space1;
 use nom::combinator::eof;
+use nom::combinator::not;
 use nom::combinator::opt;
+use nom::combinator::peek;
 use nom::combinator::recognize;
 use nom::combinator::verify;
+use nom::multi::many0;
 use nom::multi::many1;
 use nom::multi::many_till;
 use nom::sequence::tuple;
@@ -163,7 +166,7 @@ pub fn plain_list_item<'r, 's>(
         parser_with_context!(item_tag)(context),
         tag(" ::"),
     )))(remaining)?;
-    let (remaining, _ws) = alt((space1, line_ending))(remaining)?;
+    let (remaining, _ws) = item_tag_post_gap(context, remaining)?;
     let exit_matcher = plain_list_item_end(indent_level);
     let parser_context = context
         .with_additional_node(ContextElement::ConsumeTrailingWhitespace(true))
@@ -174,7 +177,10 @@ pub fn plain_list_item<'r, 's>(
 
     let (remaining, (children, _exit_contents)) = many_till(
         parser_with_context!(element(true))(&parser_context),
-        parser_with_context!(exit_matcher_parser)(&parser_context),
+        alt((
+            peek(recognize(tuple((start_of_line, many0(blank_line), eof)))),
+            parser_with_context!(exit_matcher_parser)(&parser_context),
+        )),
     )(remaining)?;
 
     let (remaining, _trailing_ws) =
@@ -189,7 +195,7 @@ pub fn plain_list_item<'r, 's>(
             bullet: bull.into(),
             tag: maybe_tag
                 .map(|(_ws, item_tag, _divider)| item_tag)
-                .unwrap_or(Vec::new()), // TODO
+                .unwrap_or(Vec::new()),
             children,
         },
     ));
@@ -305,6 +311,27 @@ fn item_tag_end<'r, 's>(
     )))(input)
 }
 
+#[cfg_attr(feature = "tracing", tracing::instrument(ret, level = "debug"))]
+fn item_tag_post_gap<'r, 's>(
+    context: Context<'r, 's>,
+    input: OrgSource<'s>,
+) -> Res<OrgSource<'s>, OrgSource<'s>> {
+    verify(
+        recognize(tuple((
+            alt((blank_line, space0)),
+            many_till(
+                blank_line,
+                alt((
+                    peek(recognize(not(blank_line))),
+                    peek(recognize(tuple((many0(blank_line), eof)))),
+                    parser_with_context!(exit_matcher_parser)(context),
+                )),
+            ),
+        ))),
+        |gap| gap.len() > 0,
+    )(input)
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;