diff --git a/mypy/checker.py b/mypy/checker.py
index 20a825e9cc5e..a4e7619e4e65 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -85,11 +85,13 @@
     CallExpr,
     ClassDef,
     ComparisonExpr,
+    ConditionalExpr,
     Context,
     ContinueStmt,
     Decorator,
     DelStmt,
     DictExpr,
+    DictionaryComprehension,
     EllipsisExpr,
     Expression,
     ExpressionStmt,
@@ -98,6 +100,7 @@
     FuncBase,
     FuncDef,
     FuncItem,
+    GeneratorExpr,
     GlobalDecl,
     IfStmt,
     Import,
@@ -107,6 +110,7 @@
     IndexExpr,
     IntExpr,
     LambdaExpr,
+    ListComprehension,
     ListExpr,
     Lvalue,
     MatchStmt,
@@ -124,7 +128,9 @@
     RaiseStmt,
     RefExpr,
     ReturnStmt,
+    SetComprehension,
     SetExpr,
+    SliceExpr,
     StarExpr,
     Statement,
     StrExpr,
@@ -4928,6 +4934,8 @@ def infer_context_dependent(
             return typ
 
         # If there are errors with the original type context, try re-inferring in empty context.
+        # However, skip this fallback if the expression contains assignment expressions (walrus
+        # operator), as they can cause incorrect type inference when the context is removed.
         original_messages = msg.filtered_errors()
         original_type_map = type_map
         with self.msg.filter_errors(
@@ -4937,7 +4945,12 @@ def infer_context_dependent(
                 alt_typ = get_proper_type(
                     self.expr_checker.accept(expr, None, allow_none_return=allow_none_func_call)
                 )
-        if not msg.has_new_errors() and is_subtype(alt_typ, type_ctx):
+
+        if (
+            not msg.has_new_errors()
+            and is_subtype(alt_typ, type_ctx)
+            and not self.contains_assignment_expr(expr)
+        ):
             self.store_types(type_map)
             return alt_typ
 
@@ -4979,7 +4992,10 @@ def check_return_stmt(self, s: ReturnStmt) -> None:
 
                 # Return with a value.
                 if (
-                    isinstance(s.expr, (CallExpr, ListExpr, TupleExpr, DictExpr, SetExpr, OpExpr))
+                    isinstance(
+                        s.expr,
+                        (CallExpr, ListExpr, TupleExpr, DictExpr, SetExpr, OpExpr, AssignmentExpr),
+                    )
                     or isinstance(s.expr, AwaitExpr)
                     and isinstance(s.expr.expr, CallExpr)
                 ):
@@ -5057,6 +5073,125 @@ def check_return_stmt(self, s: ReturnStmt) -> None:
                 if self.in_checked_function():
                     self.fail(message_registry.RETURN_VALUE_EXPECTED, s)
 
+    def contains_assignment_expr(self, expr: Expression) -> bool:
+        """Check if expression contains any AssignmentExpr (walrus operator)."""
+        # Base case: found an assignment expression
+        if isinstance(expr, AssignmentExpr):
+            return True
+
+        # Recursively check nested expressions in various expression types
+
+        # Container expressions
+        if isinstance(expr, (TupleExpr, ListExpr, SetExpr)):
+            return any(self.contains_assignment_expr(item) for item in expr.items)
+
+        if isinstance(expr, DictExpr):
+            # Check both keys and values
+            # DictExpr.items is list[tuple[Expression | None, Expression]]
+            for key_expr, value_expr in expr.items:
+                if key_expr is not None and self.contains_assignment_expr(key_expr):
+                    return True
+                if self.contains_assignment_expr(value_expr):
+                    return True
+            return False
+
+        # Binary operations (left and right operands)
+        if isinstance(expr, OpExpr):
+            return self.contains_assignment_expr(expr.left) or self.contains_assignment_expr(
+                expr.right
+            )
+
+        # Unary operations
+        if isinstance(expr, UnaryExpr):
+            return self.contains_assignment_expr(expr.expr)
+
+        # Comparison expressions (multiple operands)
+        if isinstance(expr, ComparisonExpr):
+            return any(self.contains_assignment_expr(operand) for operand in expr.operands)
+
+        # Function calls (check arguments)
+        if isinstance(expr, CallExpr):
+            # Check callee and all arguments
+            if self.contains_assignment_expr(expr.callee):
+                return True
+            return any(self.contains_assignment_expr(arg) for arg in expr.args)
+
+        # Index expressions (subscripts)
+        if isinstance(expr, IndexExpr):
+            if self.contains_assignment_expr(expr.base):
+                return True
+            return self.contains_assignment_expr(expr.index)
+
+        # Member access
+        if isinstance(expr, MemberExpr):
+            return self.contains_assignment_expr(expr.expr)
+
+        # Starred expressions (unpacking)
+        if isinstance(expr, StarExpr):
+            return self.contains_assignment_expr(expr.expr)
+
+        # Await expressions
+        if isinstance(expr, AwaitExpr):
+            return self.contains_assignment_expr(expr.expr)
+
+        # Yield expressions
+        if isinstance(expr, YieldExpr):
+            if expr.expr is not None:
+                return self.contains_assignment_expr(expr.expr)
+            return False
+
+        # Conditional expressions (ternary operator: x if cond else y)
+        if isinstance(expr, ConditionalExpr):
+            return (
+                self.contains_assignment_expr(expr.cond)
+                or self.contains_assignment_expr(expr.if_expr)
+                or self.contains_assignment_expr(expr.else_expr)
+            )
+
+        # Slice expressions (x:y:z)
+        if isinstance(expr, SliceExpr):
+            return (
+                (expr.begin_index is not None and self.contains_assignment_expr(expr.begin_index))
+                or (expr.end_index is not None and self.contains_assignment_expr(expr.end_index))
+                or (expr.stride is not None and self.contains_assignment_expr(expr.stride))
+            )
+
+        # Generator expressions and comprehensions
+        if isinstance(expr, GeneratorExpr):
+            if self.contains_assignment_expr(expr.left_expr):
+                return True
+            for seq in expr.sequences:
+                if self.contains_assignment_expr(seq):
+                    return True
+            for condlist in expr.condlists:
+                for cond in condlist:
+                    if self.contains_assignment_expr(cond):
+                        return True
+            return False
+
+        if isinstance(expr, ListComprehension):
+            return self.contains_assignment_expr(expr.generator)
+
+        if isinstance(expr, SetComprehension):
+            return self.contains_assignment_expr(expr.generator)
+
+        if isinstance(expr, DictionaryComprehension):
+            if self.contains_assignment_expr(expr.key) or self.contains_assignment_expr(
+                expr.value
+            ):
+                return True
+            for seq in expr.sequences:
+                if self.contains_assignment_expr(seq):
+                    return True
+            for condlist in expr.condlists:
+                for cond in condlist:
+                    if self.contains_assignment_expr(cond):
+                        return True
+            return False
+
+        # All other expression types (NameExpr, IntExpr, StrExpr, etc.) don't contain nested expressions
+        return False
+
     def visit_if_stmt(self, s: IfStmt) -> None:
         """Type check an if statement."""
         # This frame records the knowledge from previous if/elif clauses not being taken.