diff --git a/mypy/test/testpythoneval.py b/mypy/test/testpythoneval.py
index 1fd342452102..17baec96cfbc 100644
--- a/mypy/test/testpythoneval.py
+++ b/mypy/test/testpythoneval.py
@@ -46,10 +46,8 @@ def test_python_evaluation(testcase: DataDrivenTestCase, cache_dir: str) -> None
     """
     assert testcase.old_cwd is not None, "test was not properly set up"
     # We must enable site packages to get access to installed stubs.
-    # TODO: Enable strict optional for these tests
     mypy_cmdline = [
         "--show-traceback",
-        "--no-strict-optional",
         "--no-silence-site-packages",
         "--no-error-summary",
         "--hide-error-codes",
diff --git a/test-data/unit/pythoneval.test b/test-data/unit/pythoneval.test
index eada8cf6fa85..b43dcbd7088f 100644
--- a/test-data/unit/pythoneval.test
+++ b/test-data/unit/pythoneval.test
@@ -63,8 +63,8 @@ print(abs(A()))
 5.5
 
 [case testAbs2]
-n = None  # type: int
-f = None  # type: float
+n: int
+f: float
 n = abs(1)
 abs(1) + 'x'  # Error
 f = abs(1.1)
@@ -95,7 +95,7 @@ print(list.__add__([1, 2], [3, 4]))
 import typing
 class A:
     x = 1
-    def f(self) -> None: print('f')
+    def f(self: typing.Optional["A"]) -> None: print('f')
 class B(A):
     pass
 B.f(None)
@@ -130,7 +130,7 @@ A docstring!
 [case testFunctionAttributes]
 import typing
 ord.__class__
-print(type(ord.__doc__ + ''))
+print(type(ord.__doc__ or '' + ''))
 print(ord.__name__)
 print(ord.__module__)
 [out]
@@ -333,25 +333,28 @@ _program.py:6: note: Revealed type is "typing.IO[Any]"
 [case testGenericPatterns]
 from typing import Pattern
 import re
-p = None  # type: Pattern[str]
+p: Pattern[str]
 p = re.compile('foo*')
-b = None  # type: Pattern[bytes]
+b: Pattern[bytes]
 b = re.compile(b'foo*')
-print(p.match('fooo').group(0))
+m = p.match('fooo')
+assert m
+print(m.group(0))
 [out]
 fooo
 
 [case testGenericMatch]
-from typing import Match
+from typing import Match, Optional
 import re
-def f(m: Match[bytes]) -> None:
+def f(m: Optional[Match[bytes]]) -> None:
+    assert m
     print(m.group(0))
 f(re.match(b'x*', b'xxy'))
 [out]
 b'xx'
 
 [case testIntFloatDucktyping]
-x = None  # type: float
+x: float
 x = 2.2
 x = 2
 def f(x: float) -> None: pass
@@ -374,18 +377,17 @@ math.sin(2)
 math.sin(2.2)
 
 [case testAbsReturnType]
-
-f = None  # type: float
-n = None  # type: int
+f: float
+n: int
 n = abs(2)
 f = abs(2.2)
 abs(2.2) + 'x'
 [out]
-_program.py:6: error: Unsupported operand types for + ("float" and "str")
+_program.py:5: error: Unsupported operand types for + ("float" and "str")
 
 [case testROperatorMethods]
-b = None  # type: bytes
-s = None  # type: str
+b: bytes
+s: str
 if int():
     s = b'foo' * 5 # Error
 if int():
@@ -434,7 +436,6 @@ True
 False
 
 [case testOverlappingOperatorMethods]
-
 class X: pass
 class A:
     def __add__(self, x) -> int:
@@ -444,11 +445,11 @@ class A:
 class B:
     def __radd__(self, x: A) -> str: return 'x'
 class C(X, B): pass
-b = None  # type: B
+b: B
 b = C()
 print(A() + b)
 [out]
-_program.py:9: error: Signatures of "__radd__" of "B" and "__add__" of "A" are unsafely overlapping
+_program.py:8: error: Signatures of "__radd__" of "B" and "__add__" of "A" are unsafely overlapping
 
 [case testBytesAndBytearrayComparisons]
 import typing
@@ -859,7 +860,7 @@ class MyDDict(t.DefaultDict[int,T], t.Generic[T]):
 MyDDict(dict)['0']
 MyDDict(dict)[0]
 [out]
-_program.py:7: error: Argument 1 to "defaultdict" has incompatible type "Type[List[Any]]"; expected "Callable[[], str]"
+_program.py:7: error: Argument 1 to "defaultdict" has incompatible type "Type[List[Any]]"; expected "Optional[Callable[[], str]]"
 _program.py:10: error: Invalid index type "str" for "defaultdict[int, str]"; expected type "int"
 _program.py:10: error: Incompatible types in assignment (expression has type "int", target has type "str")
 _program.py:20: error: Argument 1 to "tst" has incompatible type "defaultdict[str, List[<nothing>]]"; expected "defaultdict[int, List[<nothing>]]"
@@ -966,10 +967,10 @@ print(getattr(B(), 'x'))
 7
 
 [case testSortedNoError]
-from typing import Iterable, Callable, TypeVar, List, Dict
+from typing import Iterable, Callable, TypeVar, List, Dict, Optional
 T = TypeVar('T')
-def sorted(x: Iterable[T], *, key: Callable[[T], object] = None) -> None: ...
-a = None # type: List[Dict[str, str]]
+def sorted(x: Iterable[T], *, key: Optional[Callable[[T], object]] = None) -> None: ...
+a = []  # type: List[Dict[str, str]]
 sorted(a, key=lambda y: y[''])
 
 [case testAbstractProperty]
@@ -1002,9 +1003,13 @@ import re
 bre = b'a+'
 bpat = re.compile(bre)
 bpat = re.compile(bpat)
-re.search(bre, b'').groups()
+s1 = re.search(bre, b'')
+assert s1
+s1.groups()
 re.search(bre, u'') # Error
-re.search(bpat, b'').groups()
+s2 = re.search(bpat, b'')
+assert s2
+s2.groups()
 re.search(bpat, u'') # Error
 # match(), split(), findall(), finditer() are much the same, so skip those.
 # sub(), subn() have more overloads and we are checking these:
@@ -1017,11 +1022,11 @@ re.subn(bpat, b'', b'')[0] + b''
 re.subn(bre, lambda m: b'', b'')[0] + b''
 re.subn(bpat, lambda m: b'', b'')[0] + b''
 [out]
-_testReModuleBytes.py:7: error: No overload variant of "search" matches argument types "bytes", "str"
-_testReModuleBytes.py:7: note: Possible overload variants:
-_testReModuleBytes.py:7: note:     def search(pattern: Union[str, Pattern[str]], string: str, flags: Union[int, RegexFlag] = ...) -> Optional[Match[str]]
-_testReModuleBytes.py:7: note:     def search(pattern: Union[bytes, Pattern[bytes]], string: Buffer, flags: Union[int, RegexFlag] = ...) -> Optional[Match[bytes]]
-_testReModuleBytes.py:9: error: Argument 1 to "search" has incompatible type "Pattern[bytes]"; expected "Union[str, Pattern[str]]"
+_testReModuleBytes.py:9: error: No overload variant of "search" matches argument types "bytes", "str"
+_testReModuleBytes.py:9: note: Possible overload variants:
+_testReModuleBytes.py:9: note:     def search(pattern: Union[str, Pattern[str]], string: str, flags: Union[int, RegexFlag] = ...) -> Optional[Match[str]]
+_testReModuleBytes.py:9: note:     def search(pattern: Union[bytes, Pattern[bytes]], string: Buffer, flags: Union[int, RegexFlag] = ...) -> Optional[Match[bytes]]
+_testReModuleBytes.py:13: error: Argument 1 to "search" has incompatible type "Pattern[bytes]"; expected "Union[str, Pattern[str]]"
 
 [case testReModuleString]
 # Regression tests for various overloads in the re module -- string version
@@ -1029,9 +1034,13 @@ import re
 sre = 'a+'
 spat = re.compile(sre)
 spat = re.compile(spat)
-re.search(sre, '').groups()
+s1 = re.search(sre, '')
+assert s1
+s1.groups()
 re.search(sre, b'') # Error
-re.search(spat, '').groups()
+s2 = re.search(spat, '')
+assert s2
+s2.groups()
 re.search(spat, b'') # Error
 # match(), split(), findall(), finditer() are much the same, so skip those.
 # sus(), susn() have more overloads and we are checking these:
@@ -1044,11 +1053,11 @@ re.subn(spat, '', '')[0] + ''
 re.subn(sre, lambda m: '', '')[0] + ''
 re.subn(spat, lambda m: '', '')[0] + ''
 [out]
-_testReModuleString.py:7: error: No overload variant of "search" matches argument types "str", "bytes"
-_testReModuleString.py:7: note: Possible overload variants:
-_testReModuleString.py:7: note:     def search(pattern: Union[str, Pattern[str]], string: str, flags: Union[int, RegexFlag] = ...) -> Optional[Match[str]]
-_testReModuleString.py:7: note:     def search(pattern: Union[bytes, Pattern[bytes]], string: Buffer, flags: Union[int, RegexFlag] = ...) -> Optional[Match[bytes]]
-_testReModuleString.py:9: error: Argument 1 to "search" has incompatible type "Pattern[str]"; expected "Union[bytes, Pattern[bytes]]"
+_testReModuleString.py:9: error: No overload variant of "search" matches argument types "str", "bytes"
+_testReModuleString.py:9: note: Possible overload variants:
+_testReModuleString.py:9: note:     def search(pattern: Union[str, Pattern[str]], string: str, flags: Union[int, RegexFlag] = ...) -> Optional[Match[str]]
+_testReModuleString.py:9: note:     def search(pattern: Union[bytes, Pattern[bytes]], string: Buffer, flags: Union[int, RegexFlag] = ...) -> Optional[Match[bytes]]
+_testReModuleString.py:13: error: Argument 1 to "search" has incompatible type "Pattern[str]"; expected "Union[bytes, Pattern[bytes]]"
 
 [case testListSetitemTuple]
 from typing import List, Tuple
@@ -1085,7 +1094,6 @@ _program.py:17: note: Revealed type is "builtins.str"
 
 [case testTypedDictGet]
 # Test that TypedDict get plugin works with typeshed stubs
-# TODO: Make it possible to use strict optional here
 from mypy_extensions import TypedDict
 class A: pass
 D = TypedDict('D', {'x': int, 'y': str})
@@ -1097,14 +1105,14 @@ d.get()
 s = ''
 reveal_type(d.get(s))
 [out]
-_testTypedDictGet.py:7: note: Revealed type is "builtins.int"
-_testTypedDictGet.py:8: note: Revealed type is "builtins.str"
-_testTypedDictGet.py:9: note: Revealed type is "builtins.object"
-_testTypedDictGet.py:10: error: All overload variants of "get" of "Mapping" require at least one argument
-_testTypedDictGet.py:10: note: Possible overload variants:
-_testTypedDictGet.py:10: note:     def get(self, str, /) -> object
-_testTypedDictGet.py:10: note:     def [_T] get(self, str, /, default: object) -> object
-_testTypedDictGet.py:12: note: Revealed type is "builtins.object"
+_testTypedDictGet.py:6: note: Revealed type is "Union[builtins.int, None]"
+_testTypedDictGet.py:7: note: Revealed type is "Union[builtins.str, None]"
+_testTypedDictGet.py:8: note: Revealed type is "builtins.object"
+_testTypedDictGet.py:9: error: All overload variants of "get" of "Mapping" require at least one argument
+_testTypedDictGet.py:9: note: Possible overload variants:
+_testTypedDictGet.py:9: note:     def get(self, str, /) -> object
+_testTypedDictGet.py:9: note:     def [_T] get(self, str, /, default: object) -> object
+_testTypedDictGet.py:11: note: Revealed type is "builtins.object"
 
 [case testTypedDictMappingMethods]
 from mypy_extensions import TypedDict
@@ -1143,10 +1151,10 @@ _testTypedDictMappingMethods.py:16: error: Key "value" of TypedDict "Cell" canno
 _testTypedDictMappingMethods.py:21: note: Revealed type is "builtins.int"
 
 [case testCrashOnComplexCheckWithNamedTupleNext]
-from typing import NamedTuple
+from typing import NamedTuple, Optional
 
 MyNamedTuple = NamedTuple('MyNamedTuple', [('parent', 'MyNamedTuple')]) # type: ignore
-def foo(mymap) -> MyNamedTuple:
+def foo(mymap) -> Optional[MyNamedTuple]:
     return next((mymap[key] for key in mymap), None)
 [out]
 
@@ -1374,7 +1382,7 @@ JsonBlob = Dict[str, Any]
 Column = Union[List[str], List[int], List[bool], List[float], List[DateTime], List[JsonBlob]]
 
 def print_custom_table() -> None:
-    a = None  # type: Column
+    a: Column
 
     for row in simple_map(format_row, a, a, a, a, a, a, a, a):  # 8 columns
         reveal_type(row)