diff --git a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM222.py b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM222.py
index bd1282ce0f..8252420f6a 100644
--- a/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM222.py
+++ b/crates/ruff_linter/resources/test/fixtures/flake8_simplify/SIM222.py
@@ -167,3 +167,29 @@ print(f"{a}{b}" or "bar")
 print(f"{a}{''}" or "bar")
 print(f"{''}{''}" or "bar")
 print(f"{1}{''}" or "bar")
+
+
+# Regression test for: https://github.com/astral-sh/ruff/issues/14237
+for x in [*a] or [None]:
+    pass
+
+for x in {*a} or [None]:
+    pass
+
+for x in (*a,) or [None]:
+    pass
+
+for x in {**a} or [None]:
+    pass
+
+for x in [*a, *b] or [None]:
+    pass
+
+for x in {*a, *b} or [None]:
+    pass
+
+for x in (*a, *b) or [None]:
+    pass
+
+for x in {**a, **b} or [None]:
+    pass
diff --git a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM222_SIM222.py.snap b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM222_SIM222.py.snap
index ddf4598e13..bf78eede11 100644
--- a/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM222_SIM222.py.snap
+++ b/crates/ruff_linter/src/rules/flake8_simplify/snapshots/ruff_linter__rules__flake8_simplify__tests__SIM222_SIM222.py.snap
@@ -1,5 +1,6 @@
 ---
 source: crates/ruff_linter/src/rules/flake8_simplify/mod.rs
+snapshot_kind: text
 ---
 SIM222.py:1:4: SIM222 [*] Use `True` instead of `... or True`
   |
@@ -1060,5 +1061,5 @@ SIM222.py:168:7: SIM222 [*] Use `"bar"` instead of `... or "bar"`
 168     |-print(f"{''}{''}" or "bar")
     168 |+print("bar")
 169 169 | print(f"{1}{''}" or "bar")
-
-
+170 170 | 
+171 171 |
diff --git a/crates/ruff_python_ast/src/helpers.rs b/crates/ruff_python_ast/src/helpers.rs
index 3a95065cbf..13c0b89d57 100644
--- a/crates/ruff_python_ast/src/helpers.rs
+++ b/crates/ruff_python_ast/src/helpers.rs
@@ -12,8 +12,8 @@ use crate::parenthesize::parenthesized_range;
 use crate::statement_visitor::StatementVisitor;
 use crate::visitor::Visitor;
 use crate::{
-    self as ast, Arguments, CmpOp, ExceptHandler, Expr, FStringElement, MatchCase, Operator,
-    Pattern, Stmt, TypeParam,
+    self as ast, Arguments, CmpOp, DictItem, ExceptHandler, Expr, FStringElement, MatchCase,
+    Operator, Pattern, Stmt, TypeParam,
 };
 use crate::{AnyNodeRef, ExprContext};
 
@@ -1188,14 +1188,32 @@ impl Truthiness {
             | Expr::Set(ast::ExprSet { elts, .. })
             | Expr::Tuple(ast::ExprTuple { elts, .. }) => {
                 if elts.is_empty() {
-                    Self::Falsey
+                    return Self::Falsey;
+                }
+
+                if elts.iter().all(Expr::is_starred_expr) {
+                    // [*foo] / [*foo, *bar]
+                    Self::Unknown
                 } else {
                     Self::Truthy
                 }
             }
             Expr::Dict(dict) => {
                 if dict.is_empty() {
-                    Self::Falsey
+                    return Self::Falsey;
+                }
+
+                if dict.items.iter().all(|item| {
+                    matches!(
+                        item,
+                        DictItem {
+                            key: None,
+                            value: Expr::Name(..)
+                        }
+                    )
+                }) {
+                    // {**foo} / {**foo, **bar}
+                    Self::Unknown
                 } else {
                     Self::Truthy
                 }