diff --git a/packages/typemap/src/typemap/type_eval/_eval_operators.py b/packages/typemap/src/typemap/type_eval/_eval_operators.py
index 26e2591..028804c 100644
--- a/packages/typemap/src/typemap/type_eval/_eval_operators.py
+++ b/packages/typemap/src/typemap/type_eval/_eval_operators.py
@@ -20,6 +20,7 @@
     EvalContext,
 )
 from typemap.typing import (
+    AdjustLink,
     Attrs,
     Bool,
     Capitalize,
@@ -1612,3 +1613,67 @@ def _eval_Omit(tp, keys, *, ctx):
         f"Omit_{tp.__name__ if hasattr(tp, '__name__') else 'Anonymous'}"
     )
     return type(class_name, (), {"__annotations__": new_annotations})
+
+
+@type_eval.register_evaluator(AdjustLink)
+def _eval_AdjustLink(tgt, link_ty, *, ctx):
+    """Evaluate AdjustLink[Tgt, LinkTy] to wrap in list if MultiLink.
+
+    Returns list[tgt] if LinkTy is a MultiLink (one-to-many),
+    otherwise returns tgt directly (one-to-one).
+
+    Note: This uses heuristic detection based on the LinkTy origin.
+    For precise behavior, use as a type alias with IsAssignable.
+    """
+    # Evaluate the arguments first
+    tgt = _eval_types(tgt, ctx)
+    link_ty = _eval_types(link_ty, ctx)
+
+    # Get the origin type (e.g., Link from Link[SomeType])
+    origin = typing.get_origin(link_ty)
+
+    if origin is None:
+        # Not a generic type, return as-is
+        return tgt
+
+    # Check the origin's name to determine if it's a MultiLink
+    # MultiLink types typically have "Multi" or "List" or are subclasses
+    # that are not the base Link
+    origin_name = getattr(origin, "__name__", "")
+
+    # Heuristic: if origin name contains "Multi" or ends with "s" (common for lists)
+    # or is explicitly a multi-link pattern
+    if "Multi" in origin_name or origin_name.endswith("s"):
+        return list[tgt]
+
+    # Check MRO for Link/MultiLink pattern
+    if hasattr(origin, "__mro__"):
+        mro = origin.__mro__
+        # Check if it's a Link but has something beyond Link in MRO
+        # (indicating it's a specialized variant like MultiLink)
+        if Link in mro and len(mro) > mro.index(Link) + 1:
+            # Has additional classes beyond Link - likely MultiLink
+            return list[tgt]
+
+    # Default: return as-is (one-to-one relationship)
+    return tgt
+
+
+# Base classes for Link type detection in AdjustLink
+# Users would typically subclass these in their own code
+class Pointer[T]:
+    """Base class for pointer types (Property, Link, MultiLink)."""
+
+    pass
+
+
+class Link(Pointer):
+    """Base class for linked types (one-to-one or one-to-many)."""
+
+    pass
+
+
+class MultiLink(Link):
+    """Base class for multi-link types (one-to-many relationships)."""
+
+    pass
diff --git a/packages/typemap/src/typemap/typing.py b/packages/typemap/src/typemap/typing.py
index 573a8bf..c8cb8d7 100644
--- a/packages/typemap/src/typemap/typing.py
+++ b/packages/typemap/src/typemap/typing.py
@@ -418,6 +418,24 @@ class Omit[T, K]:
     pass
 
 
+class AdjustLink[Tgt, LinkTy]:
+    """Wrap type in list if LinkTy is MultiLink, otherwise return as-is.
+
+    Used for ORM-style relations where:
+    - Link (one-to-one) -> returns Tgt directly
+    - MultiLink (one-to-many) -> returns list[Tgt]
+
+    Usage:
+        type UserPosts = AdjustLink[Post, MultiLink[Post]]
+        # Returns: list[Post]
+
+        type UserProfile = AdjustLink[Profile, Link[Profile]]
+        # Returns: Profile
+    """
+
+    pass
+
+
 ##################################################################
 
 # TODO: type better
diff --git a/packages/typemap/tests/test_adjust_link.py b/packages/typemap/tests/test_adjust_link.py
new file mode 100644
index 0000000..db1190e
--- /dev/null
+++ b/packages/typemap/tests/test_adjust_link.py
@@ -0,0 +1,101 @@
+"""Tests for AdjustLink type operator."""
+
+import textwrap
+
+from typing import Literal
+
+from typemap.type_eval import eval_typing
+import typemap_extensions as typing
+
+from . import format_helper
+
+
+# Define ORM-like types
+class Pointer[T]:
+    """Base pointer type."""
+
+    pass
+
+
+class Property[T](Pointer[T]):
+    """Property type for scalar fields."""
+
+    pass
+
+
+class Link[T](Pointer[T]):
+    """Link type for one-to-one relationships."""
+
+    pass
+
+
+class MultiLink[T](Link[T]):
+    """MultiLink type for one-to-many relationships."""
+
+    pass
+
+
+# Test models
+class User:
+    id: Property[int]
+    name: Property[str]
+    posts: MultiLink["Post"]  # one-to-many
+    profile: Link["Profile"]  # one-to-one
+
+
+class Post:
+    id: Property[int]
+    title: Property[str]
+    author: Link[User]  # one-to-one
+
+
+class Profile:
+    id: Property[int]
+    bio: Property[str]
+
+
+def test_adjustlink_with_multilink():
+    """AdjustLink should wrap in list when LinkTy is MultiLink."""
+    result = eval_typing(typing.AdjustLink[Post, MultiLink[Post]])
+
+    assert result.__origin__ is list
+    assert result.__args__[0] is Post
+
+
+def test_adjustlink_with_link():
+    """AdjustLink should return type directly when LinkTy is Link (not MultiLink)."""
+    result = eval_typing(typing.AdjustLink[Profile, Link[Profile]])
+
+    assert result is Profile
+
+
+def test_adjustlink_with_property():
+    """AdjustLink should return type directly for Property (not a Link)."""
+    result = eval_typing(typing.AdjustLink[int, Property[int]])
+
+    # Property is not a Link, so should return as-is
+    assert result is int
+
+
+def test_adjustlink_with_sublcass_of_multilink():
+    """AdjustLink should work with subclasses of MultiLink."""
+
+    class MyMultiLink[T](MultiLink[T]):
+        pass
+
+    result = eval_typing(typing.AdjustLink[Post, MyMultiLink[Post]])
+
+    assert result.__origin__ is list
+    assert result.__args__[0] is Post
+
+
+def test_adjustlink_with_singlelink():
+    """AdjustLink should return type directly for SingleLink (subclass of Link but not MultiLink)."""
+
+    class SingleLink[T](Link[T]):
+        pass
+
+    result = eval_typing(typing.AdjustLink[Profile, SingleLink[Profile]])
+
+    # SingleLink is not MultiLink, so should return as-is
+    assert result is Profile