diff --git a/mypyc/codegen/emit.py b/mypyc/codegen/emit.py
index 34837a73adbd..cf648001b824 100644
--- a/mypyc/codegen/emit.py
+++ b/mypyc/codegen/emit.py
@@ -6,7 +6,7 @@
 import sys
 import textwrap
 from collections.abc import Callable
-from typing import Final
+from typing import TYPE_CHECKING, Final
 
 from mypyc.codegen.cstring import c_string_initializer
 from mypyc.codegen.literals import Literals
@@ -59,6 +59,9 @@
 from mypyc.namegen import NameGenerator, exported_name
 from mypyc.sametype import is_same_type
 
+if TYPE_CHECKING:
+    from _typeshed import SupportsWrite
+
 # Whether to insert debug asserts for all error handling, to quickly
 # catch errors propagating without exceptions set.
 DEBUG_ERRORS: Final = False
@@ -210,7 +213,8 @@ def object_annotation(self, obj: object, line: str) -> str:
 
         If it contains illegal characters, an empty string is returned."""
         line_width = self._indent + len(line)
-        formatted = pprint.pformat(obj, compact=True, width=max(90 - line_width, 20))
+        formatted = pformat_deterministic(obj, max(90 - line_width, 20))
+
         if any(x in formatted for x in ("/*", "*/", "\0")):
             return ""
 
@@ -1271,3 +1275,62 @@ def native_function_doc_initializer(func: FuncIR) -> str:
         return "NULL"
     docstring = f"{text_sig}\n--\n\n"
     return c_string_initializer(docstring.encode("ascii", errors="backslashreplace"))
+
+
+def pformat_deterministic(obj: object, width: int) -> str:
+    """Pretty-print `obj` with deterministic sorting for mypyc literal types."""
+    # Temporarily override pprint._safe_key to get deterministic ordering of containers.
+    default_safe_key = pprint._safe_key  # type: ignore [attr-defined]
+    pprint._safe_key = _mypyc_safe_key  # type: ignore [attr-defined]
+
+    try:
+        printer = _DeterministicPrettyPrinter(width=width, compact=True, sort_dicts=True)
+        return printer.pformat(obj)
+    finally:
+        # Always restore the original key to avoid affecting other pprint users.
+        pprint._safe_key = default_safe_key  # type: ignore [attr-defined]
+
+
+def _mypyc_safe_key(obj: object) -> str:
+    """A custom sort key implementation for pprint that makes the output deterministic
+    for all literal types supported by mypyc.
+
+    This is NOT safe for use as a sort key for other types, so we MUST replace the
+    original pprint._safe_key once we've pprinted our object.
+
+    Since this is a bit hacky, see for context https://github.com/python/mypy/pull/20012
+    """
+    return str(type(obj)) + pprint.pformat(obj, compact=True, sort_dicts=True)
+
+
+class _DeterministicPrettyPrinter(pprint.PrettyPrinter):
+    """PrettyPrinter that sorts set/frozenset elements deterministically."""
+
+    _dispatch = pprint.PrettyPrinter._dispatch.copy()
+
+    def _pprint_set(
+        self,
+        object: set[object] | frozenset[object],
+        stream: SupportsWrite[str],
+        indent: int,
+        allowance: int,
+        context: dict[int, int],
+        level: int,
+    ) -> None:
+        if not object:
+            stream.write(repr(object))
+            return
+        typ = type(object)
+        if typ is set:
+            stream.write("{")
+            endchar = "}"
+        else:
+            stream.write("frozenset({")
+            endchar = "})"
+            indent += len("frozenset(")
+        items = sorted(object, key=_mypyc_safe_key)
+        self._format_items(items, stream, indent, allowance + len(endchar), context, level)
+        stream.write(endchar)
+
+    _dispatch[set.__repr__] = _pprint_set
+    _dispatch[frozenset.__repr__] = _pprint_set
diff --git a/mypyc/test/test_emit.py b/mypyc/test/test_emit.py
index 1baed3964299..f52da1cd8757 100644
--- a/mypyc/test/test_emit.py
+++ b/mypyc/test/test_emit.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
+import pprint
 import unittest
 
-from mypyc.codegen.emit import Emitter, EmitterContext
+from mypyc.codegen.emit import Emitter, EmitterContext, pformat_deterministic
 from mypyc.common import HAVE_IMMORTAL
 from mypyc.ir.class_ir import ClassIR
 from mypyc.ir.ops import BasicBlock, Register, Value
@@ -21,6 +22,34 @@
 from mypyc.namegen import NameGenerator
 
 
+class TestPformatDeterministic(unittest.TestCase):
+    def test_frozenset_elements_sorted(self) -> None:
+        fs_small = frozenset({("a", 1)})
+        fs_large = frozenset({("a", 1), ("b", 2)})
+        literal_a = frozenset({fs_large, fs_small})
+        literal_b = frozenset({fs_small, fs_large})
+        expected = "frozenset({frozenset({('b', 2), ('a', 1)}), frozenset({('a', 1)})})"
+
+        assert pformat_deterministic(literal_a, 80) == expected
+        assert pformat_deterministic(literal_b, 80) == expected
+
+    def test_nested_supported_literals(self) -> None:
+        nested_frozen = frozenset({("m", 0), ("n", 1)})
+        item_a = ("outer", 1, nested_frozen)
+        item_b = ("outer", 2, frozenset({("x", 3)}))
+        literal_a = frozenset({item_a, item_b})
+        literal_b = frozenset({item_b, item_a})
+        expected = "frozenset({('outer', 2, frozenset({('x', 3)})), ('outer', 1, frozenset({('n', 1), ('m', 0)}))})"
+
+        assert pformat_deterministic(literal_a, 120) == expected
+        assert pformat_deterministic(literal_b, 120) == expected
+
+    def test_restores_default_safe_key(self) -> None:
+        original_safe_key = pprint._safe_key
+        pformat_deterministic({"key": "value"}, 80)
+        assert pprint._safe_key is original_safe_key
+
+
 class TestEmitter(unittest.TestCase):
     def setUp(self) -> None:
         self.n = Register(int_rprimitive, "n")