4 files changed, 48 insertions, 1 deletions
diff --git a/activerecord/CHANGELOG.md b/activerecord/CHANGELOG.md
index 8676f95d6d..99d9101347 100644
--- a/activerecord/CHANGELOG.md
+++ b/activerecord/CHANGELOG.md
@@ -1,3 +1,10 @@
+*   Don't raise an error if an association failed to destroy when `destroy` was
+    called on the parent (as opposed to `destroy!`).
+
+    Fixes #20991.
+
+    *Sean Griffin*
+
 *   ActiveRecord::RecordNotFound modified to store model name, primary_key and
     id of the caller model. It allows the catcher of this exception to make
     a better decision to what to do with it. For example consider this simple
diff --git a/activerecord/lib/active_record/callbacks.rb b/activerecord/lib/active_record/callbacks.rb
index 19f0dca5a6..c7c769b283 100644
--- a/activerecord/lib/active_record/callbacks.rb
+++ b/activerecord/lib/active_record/callbacks.rb
@@ -290,6 +290,9 @@ module ActiveRecord
 
     def destroy #:nodoc:
       _run_destroy_callbacks { super }
+    rescue RecordNotDestroyed => e
+      @_association_destroy_exception = e
+      false
     end
 
     def touch(*) #:nodoc:
diff --git a/activerecord/lib/active_record/persistence.rb b/activerecord/lib/active_record/persistence.rb
index 0a6e4ac0bd..09c36d7b4d 100644
--- a/activerecord/lib/active_record/persistence.rb
+++ b/activerecord/lib/active_record/persistence.rb
@@ -193,7 +193,7 @@ module ActiveRecord
     # and #destroy! raises ActiveRecord::RecordNotDestroyed.
     # See ActiveRecord::Callbacks for further details.
     def destroy!
-      destroy || raise(RecordNotDestroyed.new("Failed to destroy the record", self))
+      destroy || _raise_record_not_destroyed
     end
 
     # Returns an instance of the specified +klass+ with the attributes of the
@@ -548,5 +548,12 @@ module ActiveRecord
     def verify_readonly_attribute(name)
       raise ActiveRecordError, "#{name} is marked as readonly" if self.class.readonly_attributes.include?(name)
     end
+
+    def _raise_record_not_destroyed
+      @_association_destroy_exception ||= nil
+      raise @_association_destroy_exception || RecordNotDestroyed.new("Failed to destroy the record", self)
+    ensure
+      @_association_destroy_exception = nil
+    end
   end
 end
diff --git a/activerecord/test/cases/associations/has_many_associations_test.rb b/activerecord/test/cases/associations/has_many_associations_test.rb
index c2ef59d0f7..21e2ee3b11 100644
--- a/activerecord/test/cases/associations/has_many_associations_test.rb
+++ b/activerecord/test/cases/associations/has_many_associations_test.rb
@@ -2278,4 +2278,34 @@ class HasManyAssociationsTest < ActiveRecord::TestCase
 
     assert_deprecated { company.clients_of_firm(true) }
   end
+
+  class AuthorWithErrorDestroyingAssociation < ActiveRecord::Base
+    self.table_name = "authors"
+    has_many :posts_with_error_destroying,
+      class_name: "PostWithErrorDestroying",
+      foreign_key: :author_id,
+      dependent: :destroy
+  end
+
+  class PostWithErrorDestroying < ActiveRecord::Base
+    self.table_name = "posts"
+    self.inheritance_column = nil
+    before_destroy -> { throw :abort }
+  end
+
+  def test_destroy_does_not_raise_when_association_errors_on_destroy
+    assert_no_difference "AuthorWithErrorDestroyingAssociation.count" do
+      author = AuthorWithErrorDestroyingAssociation.first
+
+      assert_not author.destroy
+    end
+  end
+
+  def test_destroy_with_bang_bubbles_errors_from_associations
+    error = assert_raises ActiveRecord::RecordNotDestroyed do
+      AuthorWithErrorDestroyingAssociation.first.destroy!
+    end
+
+    assert_instance_of PostWithErrorDestroying, error.record
+  end
 end