diff --git a/mypy/build.py b/mypy/build.py
index c2e378290274..3ba7d4a6c0c9 100644
--- a/mypy/build.py
+++ b/mypy/build.py
@@ -40,7 +40,14 @@
     TypedDict,
 )
 
-from librt.internal import cache_version
+
+# from librt.internal import cache_version
+# from mypy.cache import CACHE_VERSION as cache_version
+def cache_version() -> int:
+    from mypy.cache import CACHE_VERSION
+
+    return CACHE_VERSION
+
 
 import mypy.semanal_main
 from mypy.cache import (
diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 9990caaeb7a1..a503930b50cb 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+# sys.exit(1)
 import enum
 import itertools
 import time
@@ -1749,7 +1750,41 @@ def check_callable_call(
             callee = callee.copy_modified(ret_type=fresh_ret_type)
 
         if callee.is_generic():
+            # import sys
+            # sys.stderr.write(f"DEBUG: Checking generic callee: {callee}\n")
             callee = freshen_function_type_vars(callee)
+            ctx = self.type_context[-1]
+            if ctx:
+                p_ctx = get_proper_type(ctx)
+                if isinstance(p_ctx, UnionType):
+                    # sys.stderr.write(f"DEBUG: Union Context found: {ctx}\n")
+                    candidates = []
+                    for item in p_ctx.items:
+                        candidate = self.infer_function_type_arguments_using_context(
+                            callee, context, type_context=item
+                        )
+                        # Filter out candidates that did not respect the context (e.g. remained generic
+                        # or inferred something incompatible).
+                        if is_subtype(candidate.ret_type, item):
+                            candidates.append(candidate)
+
+                    if candidates:
+                        # We use 'None' context to prevent infinite recursion when checking overloads
+                        # provided one of the candidates remains generic.
+                        self.type_context.append(None)
+                        try:
+                            return self.check_overload_call(
+                                Overloaded(candidates),
+                                args,
+                                arg_kinds,
+                                arg_names,
+                                callable_name,
+                                object_type,
+                                context,
+                            )
+                        finally:
+                            self.type_context.pop()
+
             callee = self.infer_function_type_arguments_using_context(callee, context)
 
         formal_to_actual = map_actuals_to_formals(
@@ -1982,7 +2017,7 @@ def infer_arg_types_in_context(
         return cast(list[Type], res)
 
     def infer_function_type_arguments_using_context(
-        self, callable: CallableType, error_context: Context
+        self, callable: CallableType, error_context: Context, type_context: Type | None = None
     ) -> CallableType:
         """Unify callable return type to type context to infer type vars.
 
@@ -1990,11 +2025,15 @@ def infer_function_type_arguments_using_context(
         of callable, and if the context is set[int], return callable modified
         by substituting 't' with 'int'.
         """
-        ctx = self.type_context[-1]
+        ctx: Type | None
+        if type_context:
+            ctx = type_context
+        else:
+            ctx = self.type_context[-1]
         if not ctx:
             return callable
         # The return type may have references to type metavariables that
-        # we are inferring right now. We must consider them as indeterminate
+        # we are inferred right now. We must consider them as indeterminate
         # and they are not potential results; thus we replace them with the
         # special ErasedType type. On the other hand, class type variables are
         # valid results.
@@ -3143,13 +3182,23 @@ def type_overrides_set(
     ) -> Iterator[None]:
         """Set _temporary_ type overrides for given expressions."""
         assert len(exprs) == len(overrides)
+        # Use a dict to store original values. This handles duplicates in exprs automatically
+        # by only storing the original value for the first occurrence (since we iterate and
+        # populate if not present).
+        original_values: dict[Expression, Type | None] = {}
         for expr, typ in zip(exprs, overrides):
+            if expr not in original_values:
+                original_values[expr] = self.type_overrides.get(expr)
             self.type_overrides[expr] = typ
         try:
             yield
         finally:
-            for expr in exprs:
-                del self.type_overrides[expr]
+            for expr, prev in original_values.items():
+                if prev is None:
+                    if expr in self.type_overrides:
+                        del self.type_overrides[expr]
+                else:
+                    self.type_overrides[expr] = prev
 
     def combine_function_signatures(self, types: list[ProperType]) -> AnyType | CallableType:
         """Accepts a list of function signatures and attempts to combine them together into a