diff --git a/lib/predicate_converter.ex b/lib/predicate_converter.ex
index 6905357..6bfefee 100644
--- a/lib/predicate_converter.ex
+++ b/lib/predicate_converter.ex
@@ -259,7 +259,11 @@ defmodule Predicates.PredicateConverter do
       )
 
   defp convert_not_eq({:single, field}, value),
-    do: dynamic([q], field(q, ^field) != ^value or is_nil(field(q, ^field)))
+    do:
+      dynamic(
+        [q],
+        field(q, ^field) != ^value or is_nil(field(q, ^field))
+      )
 
   defp convert_not_eq({:virtual, field, type, json_path}, value),
     do:
@@ -461,17 +465,32 @@ defmodule Predicates.PredicateConverter do
 
       sub_schema = get_schema(sub_association)
 
-      # define the subquery to execute the given predicates against the defined association
-      subquery =
+      association =
         from(s in sub_schema,
           select: 1,
           where:
             field(s, ^sub_association.related_key) ==
               field(parent_as(^parent_table_name), ^sub_association.owner_key)
         )
-        |> build_sub_query(sub_predicate, meta)
 
-      dynamic(exists(subquery))
+      subquery = build_sub_query(association, sub_predicate, meta)
+
+      cond do
+        sub_predicate["op"] == "not_eq" and not is_nil(sub_predicate["arg"]) ->
+          dynamic(exists(subquery) or not exists(association))
+
+        sub_predicate["op"] == "eq" and is_nil(sub_predicate["arg"]) ->
+          dynamic(exists(subquery) or not exists(association))
+
+        sub_predicate["op"] == "in" and Enum.any?(sub_predicate["arg"], &is_nil(&1)) ->
+          dynamic(exists(subquery) or not exists(association))
+
+        sub_predicate["op"] == "not_in" and not Enum.any?(sub_predicate["arg"], &is_nil(&1)) ->
+          dynamic(exists(subquery) or not exists(association))
+
+        true ->
+          dynamic(exists(subquery))
+      end
     end
   end
 
diff --git a/test/predicates_test.exs b/test/predicates_test.exs
index 4433148..9acab97 100644
--- a/test/predicates_test.exs
+++ b/test/predicates_test.exs
@@ -644,6 +644,87 @@ defmodule PredicatesTest do
                })
                |> Predicates.Repo.one()
     end
+
+    test "nil handling in associations" do
+      {3, [goethe, schiller, lessing]} =
+        Predicates.Repo.insert_all(
+          Author,
+          [%{name: "Goethe"}, %{name: "Schiller"}, %{name: "Lessing"}],
+          returning: true
+        )
+
+      # logic test
+      Predicates.Repo.insert_all(Post, [
+        %{name: "Faust", author_id: goethe.id},
+        %{name: nil, author_id: schiller.id}
+      ])
+
+      # eq and not_eq tests
+      assert [schiller, lessing] =
+               Converter.build_query(Author, %{
+                 "op" => "eq",
+                 "path" => "posts.name",
+                 "arg" => nil
+               })
+               |> Predicates.Repo.all()
+
+      assert [goethe] =
+               Converter.build_query(Author, %{
+                 "op" => "not_eq",
+                 "path" => "posts.name",
+                 "arg" => nil
+               })
+               |> Predicates.Repo.all()
+
+      assert [goethe] =
+               Converter.build_query(Author, %{
+                 "op" => "eq",
+                 "path" => "posts.name",
+                 "arg" => "Faust"
+               })
+               |> Predicates.Repo.all()
+
+      assert [schiller, lessing] =
+               Converter.build_query(Author, %{
+                 "op" => "not_eq",
+                 "path" => "posts.name",
+                 "arg" => "Faust"
+               })
+               |> Predicates.Repo.all()
+
+      # in and not_in tests
+      assert [schiller, lessing] =
+               Converter.build_query(Author, %{
+                 "op" => "in",
+                 "path" => "posts.name",
+                 "arg" => [nil]
+               })
+               |> Predicates.Repo.all()
+
+      assert [goethe] =
+               Converter.build_query(Author, %{
+                 "op" => "not_in",
+                 "path" => "posts.name",
+                 "arg" => [nil]
+               })
+               |> Predicates.Repo.all()
+
+      assert [goethe] =
+               Converter.build_query(Author, %{
+                 "op" => "in",
+                 "path" => "posts.name",
+                 "arg" => ["Faust"]
+               })
+               |> Predicates.Repo.all()
+
+      assert [schiller, lessing] =
+               Converter.build_query(Author, %{
+                 "op" => "not_in",
+                 "path" => "posts.name",
+                 "arg" => ["Faust"]
+               })
+               |> Predicates.Repo.all()
+    end
   end
 
   test "supports shorthand true/false expressions" do
@@ -756,7 +837,9 @@ defmodule PredicatesTest do
 
     test "walks association" do
       {2, [goethe, schiller]} =
-        Predicates.Repo.insert_all(Author, [%{name: "Goethe"}, %{name: "Schiller"}],
+        Predicates.Repo.insert_all(
+          Author,
+          [%{name: "Goethe"}, %{name: "Schiller"}],
           returning: true
         )