diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assign.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assign.py
index 52b143edb9..a0317eac9a 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assign.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/statement/assign.py
@@ -8,3 +8,11 @@ a2 = (
 
 # Break the last element
 a = asdf = fjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfal = 1
+
+aa = [
+    bakjdshflkjahdslkfjlasfdahjlfds
+] = dddd = ddd = fkjaödkjaföjfahlfdalfhaöfaöfhaöfha = g = [3]
+
+aaaa = ( # trailing
+    # comment
+    bbbbb) = cccccccccccccccc = 3
diff --git a/crates/ruff_python_formatter/src/expression/mod.rs b/crates/ruff_python_formatter/src/expression/mod.rs
index 121610b81c..617fd61c41 100644
--- a/crates/ruff_python_formatter/src/expression/mod.rs
+++ b/crates/ruff_python_formatter/src/expression/mod.rs
@@ -443,6 +443,10 @@ impl<'input> PreorderVisitor<'input> for CanOmitOptionalParenthesesVisitor<'inpu
 }
 
 fn has_parentheses(expr: &Expr, source: &str) -> bool {
+    has_own_parentheses(expr) || is_expression_parenthesized(AnyNodeRef::from(expr), source)
+}
+
+pub(crate) const fn has_own_parentheses(expr: &Expr) -> bool {
     matches!(
         expr,
         Expr::Dict(_)
@@ -454,7 +458,7 @@ fn has_parentheses(expr: &Expr, source: &str) -> bool {
             | Expr::DictComp(_)
             | Expr::Call(_)
             | Expr::Subscript(_)
-    ) || is_expression_parenthesized(AnyNodeRef::from(expr), source)
+    )
 }
 
 #[derive(Debug, Copy, Clone, Ord, PartialOrd, Eq, PartialEq)]
diff --git a/crates/ruff_python_formatter/src/statement/stmt_assign.rs b/crates/ruff_python_formatter/src/statement/stmt_assign.rs
index 36a53891b5..55ff07d949 100644
--- a/crates/ruff_python_formatter/src/statement/stmt_assign.rs
+++ b/crates/ruff_python_formatter/src/statement/stmt_assign.rs
@@ -1,16 +1,13 @@
-use rustpython_parser::ast::StmtAssign;
+use rustpython_parser::ast::{Expr, StmtAssign};
 
-use ruff_formatter::write;
+use ruff_formatter::{format_args, write, FormatError};
 
-use crate::expression::maybe_parenthesize_expression;
-use crate::expression::parentheses::Parenthesize;
+use crate::context::NodeLevel;
+use crate::expression::parentheses::{Parentheses, Parenthesize};
+use crate::expression::{has_own_parentheses, maybe_parenthesize_expression};
 use crate::prelude::*;
 use crate::FormatNodeRule;
 
-// Note: This currently does wrap but not the black way so the types below likely need to be
-// replaced entirely
-//
-
 #[derive(Default)]
 pub struct FormatStmtAssign;
 
@@ -23,9 +20,18 @@ impl FormatNodeRule<StmtAssign> for FormatStmtAssign {
             type_comment: _,
         } = item;
 
-        for target in targets {
-            write!(f, [target.format(), space(), text("="), space()])?;
-        }
+        let (first, rest) = targets.split_first().ok_or(FormatError::SyntaxError)?;
+
+        write!(
+            f,
+            [
+                first.format(),
+                space(),
+                text("="),
+                space(),
+                FormatTargets { targets: rest }
+            ]
+        )?;
 
         write!(
             f,
@@ -37,3 +43,58 @@ impl FormatNodeRule<StmtAssign> for FormatStmtAssign {
         )
     }
 }
+
+struct FormatTargets<'a> {
+    targets: &'a [Expr],
+}
+
+impl Format<PyFormatContext<'_>> for FormatTargets<'_> {
+    fn fmt(&self, f: &mut Formatter<PyFormatContext<'_>>) -> FormatResult<()> {
+        if let Some((first, rest)) = self.targets.split_first() {
+            let can_omit_parentheses = has_own_parentheses(first);
+
+            let group_id = if can_omit_parentheses {
+                Some(f.group_id("assignment_parentheses"))
+            } else {
+                None
+            };
+
+            let saved_level = f.context().node_level();
+            f.context_mut()
+                .set_node_level(NodeLevel::Expression(group_id));
+
+            let format_first = format_with(|f: &mut PyFormatter| {
+                let result = if can_omit_parentheses {
+                    first.format().with_options(Parentheses::Never).fmt(f)
+                } else {
+                    write!(
+                        f,
+                        [
+                            if_group_breaks(&text("(")),
+                            soft_block_indent(&first.format().with_options(Parentheses::Never)),
+                            if_group_breaks(&text(")"))
+                        ]
+                    )
+                };
+
+                f.context_mut().set_node_level(saved_level);
+
+                result
+            });
+
+            write!(
+                f,
+                [group(&format_args![
+                    format_first,
+                    space(),
+                    text("="),
+                    space(),
+                    FormatTargets { targets: rest }
+                ])
+                .with_group_id(group_id)]
+            )
+        } else {
+            Ok(())
+        }
+    }
+}
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@statement__assign.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@statement__assign.py.snap
index efcd0cca34..4134d2b91e 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@statement__assign.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@statement__assign.py.snap
@@ -14,18 +14,43 @@ a2 = (
 
 # Break the last element
 a = asdf = fjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfal = 1
+
+aa = [
+    bakjdshflkjahdslkfjlasfdahjlfds
+] = dddd = ddd = fkjaödkjaföjfahlfdalfhaöfaöfhaöfha = g = [3]
+
+aaaa = ( # trailing
+    # comment
+    bbbbb) = cccccccccccccccc = 3
 ```
 
 ## Output
 ```py
 # break left hand side
-a1akjdshflkjahdslkfjlasfdahjlfds = bakjdshflkjahdslkfjlasfdahjlfds = cakjdshflkjahdslkfjlasfdahjlfds = kjaödkjaföjfahlfdalfhaöfaöfhaöfha = fkjaödkjaföjfahlfdalfhaöfaöfhaöfha = g = 3
+a1akjdshflkjahdslkfjlasfdahjlfds = (
+    bakjdshflkjahdslkfjlasfdahjlfds
+) = (
+    cakjdshflkjahdslkfjlasfdahjlfds
+) = kjaödkjaföjfahlfdalfhaöfaöfhaöfha = fkjaödkjaföjfahlfdalfhaöfaöfhaöfha = g = 3
 
 # join left hand side
-a2 = (b2) = 2
+a2 = b2 = 2
 
 # Break the last element
-a = asdf = fjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfal = 1
+a = (
+    asdf
+) = (
+    fjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfalflaflapamsakjsdhflakjdslfjhalsdljfal
+) = 1
+
+aa = [
+    bakjdshflkjahdslkfjlasfdahjlfds
+] = dddd = ddd = fkjaödkjaföjfahlfdalfhaöfaöfhaöfha = g = [3]
+
+aaaa = (  # trailing
+    # comment
+    bbbbb
+) = cccccccccccccccc = 3
 ```