diff --git a/mypy/checker.py b/mypy/checker.py
index dde8a3441c35d..35dd2b246f936 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -1995,10 +1995,9 @@ def is_raising_or_empty(self, s: Statement) -> bool:
             if isinstance(s.expr, EllipsisExpr):
                 return True
             elif isinstance(s.expr, CallExpr):
-                self.expr_checker.msg.disable_errors()
-                typ = get_proper_type(self.expr_checker.accept(
-                    s.expr, allow_none_return=True, always_allow_any=True))
-                self.expr_checker.msg.enable_errors()
+                with self.expr_checker.msg.disable_errors():
+                    typ = get_proper_type(self.expr_checker.accept(
+                        s.expr, allow_none_return=True, always_allow_any=True))
 
                 if isinstance(typ, UninhabitedType):
                     return True
@@ -3050,14 +3049,13 @@ def check_member_assignment(self, instance_type: Type, attribute_type: Type,
         # For non-overloaded setters, the result should be type-checked like a regular assignment.
         # Hence, we first only try to infer the type by using the rvalue as type context.
         type_context = rvalue
-        self.msg.disable_errors()
-        _, inferred_dunder_set_type = self.expr_checker.check_call(
-            dunder_set_type,
-            [TempNode(instance_type, context=context), type_context],
-            [nodes.ARG_POS, nodes.ARG_POS],
-            context, object_type=attribute_type,
-            callable_name=callable_name)
-        self.msg.enable_errors()
+        with self.msg.disable_errors():
+            _, inferred_dunder_set_type = self.expr_checker.check_call(
+                dunder_set_type,
+                [TempNode(instance_type, context=context), type_context],
+                [nodes.ARG_POS, nodes.ARG_POS],
+                context, object_type=attribute_type,
+                callable_name=callable_name)
 
         # And now we in fact type check the call, to show errors related to wrong arguments
         # count, etc., replacing the type context for non-overloaded setters only.
diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 3bfe0a306446f..8c8b442b09531 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -865,12 +865,12 @@ def check_union_call_expr(self, e: CallExpr, object_type: UnionType, member: str
         res = []  # type: List[Type]
         for typ in object_type.relevant_items():
             # Member access errors are already reported when visiting the member expression.
-            self.msg.disable_errors()
-            item = analyze_member_access(member, typ, e, False, False, False,
-                                         self.msg, original_type=object_type, chk=self.chk,
-                                         in_literal_context=self.is_literal_context(),
-                                         self_type=typ)
-            self.msg.enable_errors()
+            with self.msg.disable_errors():
+                item = analyze_member_access(member, typ, e, False, False, False,
+                                            self.msg, original_type=object_type, chk=self.chk,
+                                            in_literal_context=self.is_literal_context(),
+                                            self_type=typ)
+
             narrowed = self.narrow_type_from_binder(e.callee, item, skip_non_overlapping=True)
             if narrowed is None:
                 continue
@@ -1203,12 +1203,9 @@ def infer_function_type_arguments(self, callee_type: CallableType,
             # due to partial available context information at this time, but
             # these errors can be safely ignored as the arguments will be
             # inferred again later.
-            self.msg.disable_errors()
-
-            arg_types = self.infer_arg_types_in_context(
-                callee_type, args, arg_kinds, formal_to_actual)
-
-            self.msg.enable_errors()
+            with self.msg.disable_errors():
+                arg_types = self.infer_arg_types_in_context(
+                    callee_type, args, arg_kinds, formal_to_actual)
 
             arg_pass_nums = self.get_arg_infer_passes(
                 callee_type.arg_types, formal_to_actual, len(args))
@@ -2816,12 +2813,15 @@ def check_boolean_op(self, e: OpExpr, context: Context) -> Type:
             left_map = None
 
         if right_map is None:
-            self.msg.disable_errors()
-        try:
-            right_type = self.analyze_cond_branch(right_map, e.right, left_type)
-        finally:
-            if right_map is None:
-                self.msg.enable_errors()
+            self.msg.disable_errors1()
+            right_type = self.analyze_cond_branch(map=right_map,
+                                                  node=e.right,
+                                                  context=left_type)
+            self.msg.enable_errors()
+        else:
+            right_type = self.analyze_cond_branch(map=right_map,
+                                                  node=e.right,
+                                                  context=left_type)
 
         if right_map is None:
             # The boolean expression is statically known to be the left value
diff --git a/mypy/messages.py b/mypy/messages.py
index 9038660c88246..e2a322ee94700 100644
--- a/mypy/messages.py
+++ b/mypy/messages.py
@@ -13,8 +13,9 @@
 import re
 import difflib
 from textwrap import dedent
+from contextlib import contextmanager
 
-from typing import cast, List, Dict, Any, Sequence, Iterable, Tuple, Set, Optional, Union
+from typing import cast, List, Dict, Any, Sequence, Iterable, Tuple, Set, Optional, Union, Iterator
 from typing_extensions import Final
 
 from mypy.erasetype import erase_type
@@ -136,9 +137,17 @@ def add_errors(self, messages: 'MessageBuilder') -> None:
                 for info in errs:
                     self.errors.add_error_info(info)
 
-    def disable_errors(self) -> None:
+    def disable_errors1(self) -> None:
         self.disable_count += 1
 
+    @contextmanager
+    def disable_errors(self) -> Iterator[None]:
+        self.disable_count += 1
+        try:
+            yield
+        finally:
+            self.disable_count -= 1
+
     def enable_errors(self) -> None:
         self.disable_count -= 1