diff --git a/src/parser/plain_list.rs b/src/parser/plain_list.rs
index 54a790c8..1d7549fc 100644
--- a/src/parser/plain_list.rs
+++ b/src/parser/plain_list.rs
@@ -229,20 +229,20 @@ fn plain_list_item<'b, 'g, 'r, 's>(
 
     let exit_matcher = plain_list_item_end(indent_level);
     let final_item_whitespace_cutoff = final_item_whitespace_cutoff(indent_level);
+    let final_whitespace_context = ContextElement::ExitMatcherNode(ExitMatcherNode {
+        class: ExitClass::Beta,
+        exit_matcher: &final_item_whitespace_cutoff,
+    });
+    let final_whitespace_context = context.with_additional_node(&final_whitespace_context);
     let contexts = [
         ContextElement::ConsumeTrailingWhitespace(true),
         ContextElement::ExitMatcherNode(ExitMatcherNode {
             class: ExitClass::Beta,
             exit_matcher: &exit_matcher,
         }),
-        ContextElement::ExitMatcherNode(ExitMatcherNode {
-            class: ExitClass::Beta,
-            exit_matcher: &final_item_whitespace_cutoff,
-        }),
     ];
-    let parser_context = context.with_additional_node(&contexts[0]);
+    let parser_context = final_whitespace_context.with_additional_node(&contexts[0]);
     let parser_context = parser_context.with_additional_node(&contexts[1]);
-    let parser_context = parser_context.with_additional_node(&contexts[2]);
 
     let maybe_contentless_item: Res<OrgSource<'_>, ()> =
         detect_contentless_item_contents(&parser_context, remaining);
@@ -283,8 +283,9 @@ fn plain_list_item<'b, 'g, 'r, 's>(
         bind_context!(exit_matcher_parser, &parser_context),
     )(remaining)?;
 
+    // We have to use the parser_context here to include the whitespace cut-off
     let (remaining, _trailing_ws) =
-        maybe_consume_trailing_whitespace_if_not_exiting(context, remaining)?;
+        maybe_consume_trailing_whitespace_if_not_exiting(&final_whitespace_context, remaining)?;
 
     let source = get_consumed(input, remaining);
     return Ok((