diff --git a/mypy/semanal.py b/mypy/semanal.py
index 52861230af376..eb8964b30218b 100644
--- a/mypy/semanal.py
+++ b/mypy/semanal.py
@@ -3136,7 +3136,7 @@ def process_imported_symbol(
                     node.node,
                     module_public=module_public,
                     module_hidden=module_hidden,
-                    becomes_typeinfo=True,
+                    becomes_typeinfo=node.node.becomes_typeinfo,
                 )
         # NOTE: we take the original node even for final `Var`s. This is to support
         # a common pattern when constants are re-exported (same applies to import *).
@@ -3385,6 +3385,10 @@ def visit_assignment_stmt(self, s: AssignmentStmt) -> None:
                 special_form = True
             elif self.analyze_enum_assign(s):
                 special_form = True
+        elif isinstance(s.rvalue, OpExpr):
+            # In rare cases we may need to "backtrack", and make something we thought is
+            # an alias into a regular variable, see testUnionNewSyntaxUndefinedAttrNoCrash.
+            s.rvalue.analyzed = None
 
         if special_form:
             self.record_special_form_lvalue(s)
@@ -3533,6 +3537,11 @@ def should_wait_rhs(self, rv: Expression) -> bool:
                     return True
         elif isinstance(rv, IndexExpr) and isinstance(rv.base, RefExpr):
             return self.should_wait_rhs(rv.base)
+        if isinstance(rv, OpExpr) and rv.op == "|":
+            if self.is_stub_file:
+                return False
+            if self.should_wait_rhs(rv.left) or self.should_wait_rhs(rv.right):
+                return True
         elif isinstance(rv, CallExpr) and isinstance(rv.callee, RefExpr):
             # This is only relevant for builtin SCC where things like 'TypeVar'
             # may be not ready.
@@ -3543,7 +3552,7 @@ def can_be_type_alias(self, rv: Expression, allow_none: bool = False) -> bool:
         """Is this a valid r.h.s. for an alias definition?
 
         Note: this function should be only called for expressions where self.should_wait_rhs()
-        returns False.
+        returns False, keep these two functions "in sync".
         """
         if isinstance(rv, RefExpr) and self.is_type_ref(rv, bare=True):
             return True
@@ -4251,6 +4260,9 @@ def check_and_set_up_type_alias(self, s: AssignmentStmt) -> bool:
             # annotations (see the second rule).
             return False
         if not pep_613 and not pep_695 and not self.can_be_type_alias(rvalue):
+            # Backtrack potential alias to a regular variable.
+            if existing and isinstance(existing.node, TypeAlias):
+                del self.current_symbol_table()[lvalue.name]
             return False
 
         if existing and not isinstance(existing.node, (PlaceholderNode, TypeAlias)):
@@ -6862,6 +6874,10 @@ def lookup_qualified(
                     nextsym = self.get_module_symbol(node, part)
                     namespace = node.fullname
                 elif isinstance(node, PlaceholderNode):
+                    # TODO: find a cleaner way to handle this.
+                    # We don't know if the resolved placeholder will have the attribute.
+                    # But if we try to be strict here, we will break some use cases like:
+                    #     Alias = Outer.NestedOne | Outer.NestedTwo
                     return sym
                 elif isinstance(node, TypeAlias) and node.no_args:
                     assert isinstance(node.target, ProperType)
diff --git a/test-data/unit/check-newsemanal.test b/test-data/unit/check-newsemanal.test
index f2dec80051831..8d391d4725e8a 100644
--- a/test-data/unit/check-newsemanal.test
+++ b/test-data/unit/check-newsemanal.test
@@ -75,7 +75,7 @@ from b import bad # E: Module "b" has no attribute "bad"
 [file b.py]
 # TODO: Could we generate an error here as well?
 from a import bad
-[targets a, b, a, b, a, b, a, b, __main__]
+[targets a, b, a, b, a, b, __main__]
 
 [case testNewAnalyzerExportedValuesInImportAll]
 from m import *
@@ -3248,3 +3248,71 @@ def test() -> None:
 
     class Model:
         pass
+
+[case testUnionNewSyntaxUndefinedAttrNoCrash]
+class Test(Flag):  # E: Name "Flag" is not defined
+    A = auto()  # E: Name "auto" is not defined
+    B = auto()  # E: Name "auto" is not defined
+
+AB = Test.A | Test.B
+
+[case testUnionNewSyntaxUndefinedAttrRegular]
+class Test(Flag):  # E: Name "Flag" is not defined
+    A = 1
+    B = 2
+
+AB = Test.A | Test.B
+reveal_type(AB)  # N: Revealed type is "builtins.int"
+[builtins fixtures/ops.pyi]
+
+[case testUnionNewSyntaxUndefinedAttrRegularReassign]
+class Test(Flag):  # E: Name "Flag" is not defined
+    A = 1
+    B = 2
+
+AB = Test.A | Test.B
+C = AB
+reveal_type(AB)  # N: Revealed type is "builtins.int"
+reveal_type(C)  # N: Revealed type is "builtins.int"
+[builtins fixtures/ops.pyi]
+
+[case testUnionNewSyntaxNested]
+class Test(Flag):  # E: Name "Flag" is not defined
+    class A: ...
+    class B: ...
+
+AB = Test.A | Test.B
+ab: AB
+reveal_type(ab)  # N: Revealed type is "__main__.Test.A | __main__.Test.B"
+
+[case testUnionNewSyntaxImportCycleNoCrash]
+import m
+[file m.py]
+from lib import A
+
+AB = int | A
+
+[file lib.py]
+from m import whatever  # type: ignore
+
+A = whatever.A
+
+[case testAliasToNestedClassInsideClassDependingOnAlias]
+class D(list[A]):
+    class C: ...
+
+A = D.C
+x: A
+reveal_type(x)  # N: Revealed type is "__main__.D.C"
+
+[case testUnionNewSyntaxDeepDeferral]
+# flags: --disable-error-code=used-before-def
+
+A = str | B
+
+B = C
+C = D
+class D: ...
+
+x: A
+reveal_type(x)  # N: Revealed type is "builtins.str | __main__.D"
diff --git a/test-data/unit/fixtures/ops.pyi b/test-data/unit/fixtures/ops.pyi
index df615f8f65746..ec38ae740b277 100644
--- a/test-data/unit/fixtures/ops.pyi
+++ b/test-data/unit/fixtures/ops.pyi
@@ -43,6 +43,7 @@ class int:
     def __rtruediv__(self, x: 'int') -> 'int': pass
     def __mod__(self, x: 'int') -> 'int': pass
     def __floordiv__(self, x: 'int') -> 'int': pass
+    def __or__(self, x: 'int') -> 'int': pass
     def __pow__(self, x: 'int', __modulo: Optional[int] = ...) -> Any: pass
     def __pos__(self) -> 'int': pass
     def __neg__(self) -> 'int': pass