diff --git a/mypy/checker.py b/mypy/checker.py
index 8720b4995f36..842a4a3d25a5 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -3895,12 +3895,15 @@ def conditional_type_map(expr: Expression,
     second element is a map from the expression to the type it would hold
     if it was not the proposed type, if any. None means bot, {} means top"""
     if proposed_type_ranges:
-        if len(proposed_type_ranges) == 1:
-            proposed_type = proposed_type_ranges[0].item  # Union with a single type breaks tests
-        else:
-            proposed_type = UnionType([type_range.item for type_range in proposed_type_ranges])
+        proposed_items = [type_range.item for type_range in proposed_type_ranges]
+        proposed_type = UnionType.make_simplified_union(proposed_items)
         if current_type:
-            if (not any(type_range.is_upper_bound for type_range in proposed_type_ranges)
+            if isinstance(proposed_type, AnyType):
+                # We don't really know much about the proposed type, so we shouldn't
+                # attempt to narrow anything. Instead, we broaden the expr to Any to
+                # avoid false positives
+                return {expr: proposed_type}, {}
+            elif (not any(type_range.is_upper_bound for type_range in proposed_type_ranges)
                and is_proper_subtype(current_type, proposed_type)):
                 # Expression is always of one of the types in proposed_type_ranges
                 return {}, None
diff --git a/test-data/unit/check-isinstance.test b/test-data/unit/check-isinstance.test
index 0b80a74c0110..ca3b2fb176ea 100644
--- a/test-data/unit/check-isinstance.test
+++ b/test-data/unit/check-isinstance.test
@@ -2101,6 +2101,34 @@ def f(x: Union[A, str]) -> None:
         x.method_only_in_a()
 [builtins fixtures/isinstance.pyi]
 
+[case testIsinstanceIgnoredImportDualAny]
+from typing import Any
+from foo import Bad, OtherBad  # type: ignore
+x: Any
+if isinstance(x, Bad):
+    reveal_type(x)  # N: Revealed type is 'Any'
+else:
+    reveal_type(x)  # N: Revealed type is 'Any'
+
+if isinstance(x, (Bad, OtherBad)):
+    reveal_type(x)  # N: Revealed type is 'Any'
+else:
+    reveal_type(x)  # N: Revealed type is 'Any'
+
+y: object
+if isinstance(y, Bad):
+    reveal_type(y)  # N: Revealed type is 'Any'
+else:
+    reveal_type(y)  # N: Revealed type is 'builtins.object'
+
+class Ok: pass
+z: Any
+if isinstance(z, Ok):
+    reveal_type(z)  # N: Revealed type is '__main__.Ok'
+else:
+    reveal_type(z)  # N: Revealed type is 'Any'
+[builtins fixtures/isinstance.pyi]
+
 [case testIsInstanceInitialNoneCheckSkipsImpossibleCasesNoStrictOptional]
 # flags: --strict-optional
 from typing import Optional, Union