diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/await.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/await.py
new file mode 100644
index 0000000000..f5319a8195
--- /dev/null
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/await.py
@@ -0,0 +1,12 @@
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = await self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = await (self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+))
+
+result = await (1 + f(1, 2, 3,))
+
+result = (await (1 + f(1, 2, 3,)))
diff --git a/crates/ruff_python_formatter/src/expression/expr_await.rs b/crates/ruff_python_formatter/src/expression/expr_await.rs
index 665fec2489..50427d95b1 100644
--- a/crates/ruff_python_formatter/src/expression/expr_await.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_await.rs
@@ -3,7 +3,9 @@ use ruff_python_ast::node::AnyNodeRef;
 use ruff_python_ast::ExprAwait;
 
 use crate::expression::maybe_parenthesize_expression;
-use crate::expression::parentheses::{NeedsParentheses, OptionalParentheses, Parenthesize};
+use crate::expression::parentheses::{
+    is_expression_parenthesized, NeedsParentheses, OptionalParentheses, Parenthesize,
+};
 use crate::prelude::*;
 
 #[derive(Default)]
@@ -28,12 +30,14 @@ impl NeedsParentheses for ExprAwait {
     fn needs_parentheses(
         &self,
         parent: AnyNodeRef,
-        _context: &PyFormatContext,
+        context: &PyFormatContext,
     ) -> OptionalParentheses {
         if parent.is_expr_await() {
             OptionalParentheses::Always
+        } else if is_expression_parenthesized(self.value.as_ref().into(), context.source()) {
+            OptionalParentheses::Never
         } else {
-            OptionalParentheses::Multiline
+            self.value.needs_parentheses(self.into(), context)
         }
     }
 }
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__await.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__await.py.snap
new file mode 100644
index 0000000000..c623da8319
--- /dev/null
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__await.py.snap
@@ -0,0 +1,52 @@
+---
+source: crates/ruff_python_formatter/tests/fixtures.rs
+input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/await.py
+---
+## Input
+```py
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = await self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = await (self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+))
+
+result = await (1 + f(1, 2, 3,))
+
+result = (await (1 + f(1, 2, 3,)))
+```
+
+## Output
+```py
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = await self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = await self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = await (
+    1
+    + f(
+        1,
+        2,
+        3,
+    )
+)
+
+result = await (
+    1
+    + f(
+        1,
+        2,
+        3,
+    )
+)
+```
+
+
+