diff --git a/compiler/rustc_ast_pretty/src/pprust/state/expr.rs b/compiler/rustc_ast_pretty/src/pprust/state/expr.rs
index ee49246a4bbf3..f6b5ff404db65 100644
--- a/compiler/rustc_ast_pretty/src/pprust/state/expr.rs
+++ b/compiler/rustc_ast_pretty/src/pprust/state/expr.rs
@@ -386,18 +386,44 @@ impl<'a> State<'a> {
 
         let ib = self.ibox(INDENT_UNIT);
 
-        // The Match subexpression in `match x {} - 1` must be parenthesized if
-        // it is the leftmost subexpression in a statement:
-        //
-        //     (match x {}) - 1;
-        //
-        // But not otherwise:
-        //
-        //     let _ = match x {} - 1;
-        //
-        // Same applies to a small set of other expression kinds which eagerly
-        // terminate a statement which opens with them.
-        let needs_par = fixup.would_cause_statement_boundary(expr);
+        let needs_par = {
+            // The Match subexpression in `match x {} - 1` must be parenthesized
+            // if it is the leftmost subexpression in a statement:
+            //
+            //     (match x {}) - 1;
+            //
+            // But not otherwise:
+            //
+            //     let _ = match x {} - 1;
+            //
+            // Same applies to a small set of other expression kinds which
+            // eagerly terminate a statement which opens with them.
+            fixup.would_cause_statement_boundary(expr)
+        } || {
+            // If a binary operation ends up with an attribute, such as
+            // resulting from the following macro expansion, then parentheses
+            // are required so that the attribute encompasses the right
+            // subexpression and not just the left one.
+            //
+            //     #![feature(stmt_expr_attributes)]
+            //
+            //     macro_rules! add_attr {
+            //         ($e:expr) => { #[attr] $e };
+            //     }
+            //
+            //     let _ = add_attr!(1 + 1);
+            //
+            // We must pretty-print `#[attr] (1 + 1)` not `#[attr] 1 + 1`.
+            !attrs.is_empty()
+                && matches!(
+                    expr.kind,
+                    ast::ExprKind::Binary(..)
+                        | ast::ExprKind::Cast(..)
+                        | ast::ExprKind::Assign(..)
+                        | ast::ExprKind::AssignOp(..)
+                        | ast::ExprKind::Range(..)
+                )
+        };
         if needs_par {
             self.popen();
             fixup = FixupContext::default();
diff --git a/tests/ui-fulldeps/pprust-parenthesis-insertion.rs b/tests/ui-fulldeps/pprust-parenthesis-insertion.rs
index 90e07bed40e75..72b5cfb90630a 100644
--- a/tests/ui-fulldeps/pprust-parenthesis-insertion.rs
+++ b/tests/ui-fulldeps/pprust-parenthesis-insertion.rs
@@ -92,6 +92,21 @@ static EXPRS: &[&str] = &[
     "#[attr] loop {}.field",
     "(#[attr] loop {}).field",
     "loop { #![attr] }.field",
+    // Attributes on a Binary, Cast, Assign, AssignOp, and Range expression
+    // require parentheses. Without parentheses `#[attr] lo..hi` means
+    // `(#[attr] lo)..hi`, and `#[attr] ..hi` is invalid syntax.
+    "#[attr] (1 + 1)",
+    "#[attr] (1 as T)",
+    "#[attr] (x = 1)",
+    "#[attr] (x += 1)",
+    "#[attr] (lo..hi)",
+    "#[attr] (..hi)",
+    // If the attribute were not present on the binary operation, it would be
+    // legal to render this without not just the inner parentheses, but also the
+    // outer ones. `return x + .. .field` (Yes, really.) Currently the
+    // pretty-printer does not take advantage of this edge case.
+    "(return #[attr] (x + ..)).field",
+    "(return x + ..).field",
     // Grammar restriction: break value starting with a labeled loop is not
     // allowed, except if the break is also labeled.
     "break 'outer 'inner: loop {} + 2",
@@ -158,7 +173,12 @@ struct Unparenthesize;
 impl MutVisitor for Unparenthesize {
     fn visit_expr(&mut self, e: &mut Expr) {
         while let ExprKind::Paren(paren) = &mut e.kind {
+            let paren_attrs = mem::take(&mut e.attrs);
             *e = mem::replace(paren, Expr::dummy());
+            if !paren_attrs.is_empty() {
+                assert!(e.attrs.is_empty());
+                e.attrs = paren_attrs;
+            }
         }
         mut_visit::walk_expr(self, e);
     }