diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/yield.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/yield.py
index 0959855cf5..8700b7ac06 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/yield.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/yield.py
@@ -104,3 +104,20 @@ yield (
 yield "#   * Make sure each ForeignKey and OneToOneField has `on_delete` set "    "to the desired behavior"
 yield "#   * Remove `managed = False` lines if you wish to allow " "Django to create, modify, and delete the table"
 yield "# Feel free to rename the models, but don't rename db_table values or "    "field names."
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = yield self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = yield (self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+))
+
+result = yield
+
+result = yield (1 + f(1, 2, 3,))
+
+result = (yield (1 + f(1, 2, 3,)))
+
+print((yield x))
diff --git a/crates/ruff_python_formatter/src/expression/expr_yield.rs b/crates/ruff_python_formatter/src/expression/expr_yield.rs
index a0d9526dc6..11765d6184 100644
--- a/crates/ruff_python_formatter/src/expression/expr_yield.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_yield.rs
@@ -4,7 +4,9 @@ use ruff_python_ast::{Expr, ExprYield, ExprYieldFrom};
 use ruff_text_size::{Ranged, TextRange};
 
 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::*;
 
 pub(super) enum AnyExpressionYield<'a> {
@@ -38,7 +40,7 @@ impl NeedsParentheses for AnyExpressionYield<'_> {
     fn needs_parentheses(
         &self,
         parent: AnyNodeRef,
-        _context: &PyFormatContext,
+        context: &PyFormatContext,
     ) -> OptionalParentheses {
         // According to https://docs.python.org/3/reference/grammar.html There are two situations
         // where we do not want to always parenthesize a yield expression:
@@ -47,8 +49,24 @@ impl NeedsParentheses for AnyExpressionYield<'_> {
         // We catch situation 1 below. Situation 2 does not need to be handled here as
         // FormatStmtExpr, does not add parenthesis
         if parent.is_stmt_assign() || parent.is_stmt_ann_assign() || parent.is_stmt_aug_assign() {
-            OptionalParentheses::Multiline
+            if let Some(value) = self.value() {
+                if is_expression_parenthesized(
+                    value.into(),
+                    context.comments().ranges(),
+                    context.source(),
+                ) {
+                    // Ex) `x = yield (1)`
+                    OptionalParentheses::Never
+                } else {
+                    // Ex) `x = yield f(1, 2, 3)`
+                    value.needs_parentheses(self.into(), context)
+                }
+            } else {
+                // Ex) `x = yield`
+                OptionalParentheses::Never
+            }
         } else {
+            // Ex) `print((yield))`
             OptionalParentheses::Always
         }
     }
@@ -94,7 +112,7 @@ impl Format<PyFormatContext<'_>> for AnyExpressionYield<'_> {
             )?;
         } else {
             // ExprYieldFrom always has Some(value) so we should never get a bare `yield from`
-            write!(f, [&token(keyword)])?;
+            write!(f, [token(keyword)])?;
         }
         Ok(())
     }
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__yield.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__yield.py.snap
index 7c78a36180..e6f39afa29 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__yield.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__yield.py.snap
@@ -110,6 +110,23 @@ yield (
 yield "#   * Make sure each ForeignKey and OneToOneField has `on_delete` set "    "to the desired behavior"
 yield "#   * Remove `managed = False` lines if you wish to allow " "Django to create, modify, and delete the table"
 yield "# Feel free to rename the models, but don't rename db_table values or "    "field names."
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = yield self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = yield (self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+))
+
+result = yield
+
+result = yield (1 + f(1, 2, 3,))
+
+result = (yield (1 + f(1, 2, 3,)))
+
+print((yield x))
 ```
 
 ## Output
@@ -230,6 +247,39 @@ yield (
     "# Feel free to rename the models, but don't rename db_table values or "
     "field names."
 )
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/7420
+result = yield self.request(
+    f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+)
+
+result = yield (
+    self.request(
+        f"/applications/{int(application_id)}/guilds/{int(scope)}/commands/{int(command_id)}/permissions"
+    )
+)
+
+result = yield
+
+result = yield (
+    1
+    + f(
+        1,
+        2,
+        3,
+    )
+)
+
+result = yield (
+    1
+    + f(
+        1,
+        2,
+        3,
+    )
+)
+
+print((yield x))
 ```