diff --git a/mypy/constraints.py b/mypy/constraints.py
index 6416791fa74a8..bf69da468a69c 100644
--- a/mypy/constraints.py
+++ b/mypy/constraints.py
@@ -411,18 +411,15 @@ def _infer_constraints(
         # When the template is a union, we are okay with leaving some
         # type variables indeterminate. This helps with some special
         # cases, though this isn't very principled.
-        result = any_constraints(
+        if has_recursive_types(template) and not has_recursive_types(actual):
+            return handle_recursive_union(template, actual, direction)
+        return any_constraints(
             [
                 infer_constraints_if_possible(t_item, actual, direction)
                 for t_item in template.items
             ],
             eager=isinstance(actual, AnyType),
         )
-        if result:
-            return result
-        elif has_recursive_types(template) and not has_recursive_types(actual):
-            return handle_recursive_union(template, actual, direction)
-        return []
 
     # Remaining cases are handled by ConstraintBuilderVisitor.
     return template.accept(ConstraintBuilderVisitor(actual, direction, skip_neg_op))
@@ -535,13 +532,12 @@ def any_constraints(options: list[list[Constraint] | None], *, eager: bool) -> l
         # Multiple sets of constraints that are all the same. Just pick any one of them.
         return valid_options[0]
 
-    if all(is_similar_constraints(valid_options[0], c) for c in valid_options[1:]):
+    all_similar = all(is_similar_constraints(valid_options[0], c) for c in valid_options[1:])
+    if all_similar:
         # All options have same structure. In this case we can merge-in trivial
         # options (i.e. those that only have Any) and try again.
-        # TODO: More generally, if a given (variable, direction) pair appears in
-        # every option, combine the bounds with meet/join always, not just for Any.
         trivial_options = select_trivial(valid_options)
-        if trivial_options and len(trivial_options) < len(valid_options):
+        if 0 < len(trivial_options) < len(valid_options):
             merged_options = []
             for option in valid_options:
                 if option in trivial_options:
@@ -563,6 +559,31 @@ def any_constraints(options: list[list[Constraint] | None], *, eager: bool) -> l
     if filtered_options != options:
         return any_constraints(filtered_options, eager=eager)
 
+    if (
+        eager
+        and all_similar
+        and not any(isinstance(c.target, ErasedType) for group in valid_options for c in group)
+    ):
+        # Now we know all constraints might be satisfiable and have similar structure.
+        # Solver will apply meets and joins as necessary, but Any should be forced into
+        # union to survive during meet.
+        # If any targets are erased, fall back to empty, otherwise they will be discarded
+        # by solver, causing false early matches.
+        cmap: dict[TypeVarId, list[Constraint]] = {}
+        for option in valid_options:
+            for c in option:
+                cmap.setdefault(c.type_var, []).append(c)
+        out: list[Constraint] = []
+        for group in cmap.values():
+            if any(isinstance(get_proper_type(c.target), AnyType) for c in group):
+                group = [
+                    merge_with_any(c)
+                    for c in group
+                    if not isinstance(get_proper_type(c.target), AnyType)
+                ]
+            out.extend(dict.fromkeys(group))
+        return out
+
     # Otherwise, there are either no valid options or multiple, inconsistent valid
     # options. Give up and deduce nothing.
     return []
diff --git a/test-data/unit/check-inference-context.test b/test-data/unit/check-inference-context.test
index 5a674cca09da3..d31b482db8e35 100644
--- a/test-data/unit/check-inference-context.test
+++ b/test-data/unit/check-inference-context.test
@@ -1530,3 +1530,33 @@ def check3(use: bool, val: str) -> "str | Literal[False]":
 def check4(use: bool, val: str) -> "str | bool":
     return use and identity(val)
 [builtins fixtures/tuple.pyi]
+
+[case testDictOrLiteralInContext]
+from typing import Union, Optional, Any
+
+P = dict[str, Union[Optional[str], dict[str, Optional[str]]]]
+
+def f(x: P) -> None:
+    pass
+
+def g(x: Union[dict[str, Any], None], s: Union[str, None]) -> None:
+    f(x or {'x': s})
+[builtins fixtures/dict.pyi]
+
+[case testInferConstrainedTypeVarInUnion]
+from typing import Generic, TypeVar, Union
+
+_S_co = TypeVar("_S_co", str, int, covariant=True)
+_S = TypeVar("_S", str, int)
+
+class HasFoo(Generic[_S_co]):
+    def foo(self) -> _S_co: ...
+
+def walk(path: Union[_S, HasFoo[_S]]) -> None:
+    ...
+
+class Path(HasFoo[str]):
+    def foo(self) -> str: ...
+
+walk(Path())
+[builtins fixtures/tuple.pyi]