diff --git a/crates/air_r_formatter/src/comments.rs b/crates/air_r_formatter/src/comments.rs
index fa77b1ed..60fbd62f 100644
--- a/crates/air_r_formatter/src/comments.rs
+++ b/crates/air_r_formatter/src/comments.rs
@@ -152,16 +152,55 @@ fn handle_empty_statement_comment(
 
     match comment.text_position() {
         CommentTextPosition::EndOfLine => match (preceding, following) {
+            (Some(preceding), Some(following)) => {
+                // Is the comment on the same line as the closest non-empty `preceding` node?
+                let is_on_preceding_line = comment.preceding_node().is_some_and(|preceding| {
+                    preceding
+                        .siblings(Direction::Prev)
+                        .take_while(|sibling| REmptyStatement::can_cast(sibling.kind()))
+                        .all(|sibling| !sibling.has_leading_newline())
+                });
+
+                if is_on_preceding_line {
+                    // ```r
+                    // {
+                    //   1; ; # Trails preceding
+                    //   2
+                    // }
+                    // ```
+                    CommentPlacement::trailing(preceding, comment)
+                } else {
+                    // Leading keeps the relative ordering here:
+                    //
+                    // ```r
+                    // {
+                    //   1
+                    //   # Leads following 1
+                    //   ; # Leads following 2
+                    //   2
+                    // }
+                    // ```
+                    //
+                    // And generally also makes sense here where the `;` is
+                    // simply removed and the comment doesn't move
+                    //
+                    // ```r
+                    // {
+                    //   1
+                    //   ; # Leads following
+                    //   2
+                    // }
+                    //
+                    // ```
+                    CommentPlacement::leading(following, comment)
+                }
+            }
+
             // ```r
             // {
-            //   1
-            //   ; # Trails preceding
-            //   2
+            //   1; ; # Trails preceding
             // }
-            // ```
-            (Some(preceding), Some(_)) => CommentPlacement::trailing(preceding, comment),
-
-            // ```r
+            //
             // {
             //   1
             //   ; # Trails preceding
diff --git a/crates/air_r_formatter/src/r/auxiliary/empty_statement.rs b/crates/air_r_formatter/src/r/auxiliary/empty_statement.rs
index 8bfdfc1f..0099e93f 100644
--- a/crates/air_r_formatter/src/r/auxiliary/empty_statement.rs
+++ b/crates/air_r_formatter/src/r/auxiliary/empty_statement.rs
@@ -527,6 +527,51 @@ mod test {
         Ok(())
     }
 
+    #[test]
+    fn test_comments_around_lone_semicolon_keep_order() -> anyhow::Result<()> {
+        let source = "\
+{
+  1
+  # a
+  ; # b
+  2
+}";
+        let expected = "\
+{
+  1
+  # a
+  # b
+  2
+}
+";
+        let tree = root([statement(braces(
+            token(L_CURLY, &[], "{", &[]),
+            [
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "1",
+                    &[],
+                ))),
+                empty(token(
+                    SEMICOLON,
+                    &[Newline, INDENT, Comment("# a"), Newline, INDENT],
+                    ";",
+                    &[SPACE, Comment("# b")],
+                )),
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "2",
+                    &[],
+                ))),
+            ],
+            token(R_CURLY, &[Newline], "}", &[]),
+        ))]);
+        assert_eq!(format(tree, source)?, expected);
+        Ok(())
+    }
+
     /// Handles every variant of [crate::comments::handle_empty_statement_comment]
     #[test]
     fn test_handle_empty_statement_comment() -> anyhow::Result<()> {
@@ -538,8 +583,37 @@ mod test {
 
         let source = "\
 {
-  1
-  ; # Trails preceding
+  1; ; # Trails preceding
+  2
+}";
+        let expected = "\
+{
+  1 # Trails preceding
+  2
+}
+";
+        let tree = root([statement(braces(
+            token(L_CURLY, &[], "{", &[]),
+            [
+                statement_with_semicolon(
+                    double(token(R_DOUBLE_LITERAL, &[Newline, INDENT], "1", &[])),
+                    token(SEMICOLON, &[], ";", &[]),
+                ),
+                empty(token(SEMICOLON, &[SPACE], ";", &[SPACE, TRAILS])),
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "2",
+                    &[],
+                ))),
+            ],
+            token(R_CURLY, &[Newline], "}", &[]),
+        ))]);
+        assert_eq!(format(tree, source)?, expected);
+
+        let source = "\
+{
+  1; ; ; # Trails preceding
   2
 }";
         let expected = "\
@@ -547,6 +621,39 @@ mod test {
   1 # Trails preceding
   2
 }
+";
+        let tree = root([statement(braces(
+            token(L_CURLY, &[], "{", &[]),
+            [
+                statement_with_semicolon(
+                    double(token(R_DOUBLE_LITERAL, &[Newline, INDENT], "1", &[])),
+                    token(SEMICOLON, &[], ";", &[]),
+                ),
+                empty(token(SEMICOLON, &[SPACE], ";", &[])),
+                empty(token(SEMICOLON, &[SPACE], ";", &[SPACE, TRAILS])),
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "2",
+                    &[],
+                ))),
+            ],
+            token(R_CURLY, &[Newline], "}", &[]),
+        ))]);
+        assert_eq!(format(tree, source)?, expected);
+
+        let source = "\
+{
+  1
+  ; ; # Leads following
+  2
+}";
+        let expected = "\
+{
+  1
+  # Leads following
+  2
+}
 ";
         let tree = root([statement(braces(
             token(L_CURLY, &[], "{", &[]),
@@ -557,7 +664,42 @@ mod test {
                     "1",
                     &[],
                 ))),
-                empty(token(SEMICOLON, &[Newline, INDENT], ";", &[SPACE, TRAILS])),
+                empty(token(SEMICOLON, &[Newline, INDENT], ";", &[])),
+                empty(token(SEMICOLON, &[SPACE], ";", &[SPACE, LEADS])),
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "2",
+                    &[],
+                ))),
+            ],
+            token(R_CURLY, &[Newline], "}", &[]),
+        ))]);
+        assert_eq!(format(tree, source)?, expected);
+
+        let source = "\
+{
+  1
+  ; # Leads following
+  2
+}";
+        let expected = "\
+{
+  1
+  # Leads following
+  2
+}
+";
+        let tree = root([statement(braces(
+            token(L_CURLY, &[], "{", &[]),
+            [
+                statement(double(token(
+                    R_DOUBLE_LITERAL,
+                    &[Newline, INDENT],
+                    "1",
+                    &[],
+                ))),
+                empty(token(SEMICOLON, &[Newline, INDENT], ";", &[SPACE, LEADS])),
                 statement(double(token(
                     R_DOUBLE_LITERAL,
                     &[Newline, INDENT],