diff --git a/app/models/account.rb b/app/models/account.rb
index dd95023a2..d2a86eaf2 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -36,7 +36,7 @@ class Account < ApplicationRecord
     manual.where.not(status: :pending_deletion)
   }
 
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   delegated_type :accountable, types: Accountable::TYPES, dependent: :destroy
   delegate :subtype, to: :accountable, allow_nil: true
diff --git a/app/models/coinbase_item.rb b/app/models/coinbase_item.rb
index 667223a23..f67aeb753 100644
--- a/app/models/coinbase_item.rb
+++ b/app/models/coinbase_item.rb
@@ -24,7 +24,7 @@ class CoinbaseItem < ApplicationRecord
   validates :api_secret, presence: true
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :coinbase_accounts, dependent: :destroy
   has_many :accounts, through: :coinbase_accounts
diff --git a/app/models/coinstats_item.rb b/app/models/coinstats_item.rb
index 72da54d1f..c2c9f51fd 100644
--- a/app/models/coinstats_item.rb
+++ b/app/models/coinstats_item.rb
@@ -22,7 +22,7 @@ class CoinstatsItem < ApplicationRecord
   validates :api_key, presence: true
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :coinstats_accounts, dependent: :destroy
   has_many :accounts, through: :coinstats_accounts
diff --git a/app/models/enable_banking_item.rb b/app/models/enable_banking_item.rb
index 8e84cdb62..7de761bde 100644
--- a/app/models/enable_banking_item.rb
+++ b/app/models/enable_banking_item.rb
@@ -17,7 +17,7 @@ class EnableBankingItem < ApplicationRecord
   validates :client_certificate, presence: true, on: :create
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :enable_banking_accounts, dependent: :destroy
   has_many :accounts, through: :enable_banking_accounts
diff --git a/app/models/lunchflow_item.rb b/app/models/lunchflow_item.rb
index 9f4f4cc7a..1165ba836 100644
--- a/app/models/lunchflow_item.rb
+++ b/app/models/lunchflow_item.rb
@@ -14,7 +14,7 @@ class LunchflowItem < ApplicationRecord
   validates :api_key, presence: true, on: :create
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :lunchflow_accounts, dependent: :destroy
   has_many :accounts, through: :lunchflow_accounts
diff --git a/app/models/mercury_item.rb b/app/models/mercury_item.rb
index a6bcaeb99..2c781265a 100644
--- a/app/models/mercury_item.rb
+++ b/app/models/mercury_item.rb
@@ -21,7 +21,7 @@ class MercuryItem < ApplicationRecord
   validates :token, presence: true, on: :create
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :mercury_accounts, dependent: :destroy
   has_many :accounts, through: :mercury_accounts
diff --git a/app/models/pdf_import.rb b/app/models/pdf_import.rb
index 0e0250462..90cb3379d 100644
--- a/app/models/pdf_import.rb
+++ b/app/models/pdf_import.rb
@@ -1,5 +1,5 @@
 class PdfImport < Import
-  has_one_attached :pdf_file
+  has_one_attached :pdf_file, dependent: :purge_later
 
   validates :document_type, inclusion: { in: DOCUMENT_TYPES }, allow_nil: true
 
diff --git a/app/models/plaid_item.rb b/app/models/plaid_item.rb
index c7f325134..4ac59d0cf 100644
--- a/app/models/plaid_item.rb
+++ b/app/models/plaid_item.rb
@@ -17,7 +17,7 @@ class PlaidItem < ApplicationRecord
   before_destroy :remove_plaid_item
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :plaid_accounts, dependent: :destroy
   has_many :legacy_accounts, through: :plaid_accounts, source: :account
diff --git a/app/models/simplefin_item.rb b/app/models/simplefin_item.rb
index 07039ad77..253b6098c 100644
--- a/app/models/simplefin_item.rb
+++ b/app/models/simplefin_item.rb
@@ -20,7 +20,7 @@ class SimplefinItem < ApplicationRecord
   before_destroy :remove_simplefin_item
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :simplefin_accounts, dependent: :destroy
   has_many :legacy_accounts, through: :simplefin_accounts, source: :account
diff --git a/app/models/snaptrade_item.rb b/app/models/snaptrade_item.rb
index 365d6af3f..0c627d7d3 100644
--- a/app/models/snaptrade_item.rb
+++ b/app/models/snaptrade_item.rb
@@ -29,7 +29,7 @@ class SnaptradeItem < ApplicationRecord
   # via ensure_user_registered!, so we don't validate them on create
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :snaptrade_accounts, dependent: :destroy
   has_many :linked_accounts, through: :snaptrade_accounts
diff --git a/app/models/user.rb b/app/models/user.rb
index 3ab9276f8..df8f9fc5e 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -59,7 +59,7 @@ class User < ApplicationRecord
     User.exists? ? fallback_role : :super_admin
   end
 
-  has_one_attached :profile_image do |attachable|
+  has_one_attached :profile_image, dependent: :purge_later do |attachable|
     attachable.variant :thumbnail, resize_to_fill: [ 300, 300 ], convert: :webp, saver: { quality: 80 }
     attachable.variant :small, resize_to_fill: [ 72, 72 ], convert: :webp, saver: { quality: 80 }, preprocessed: true
   end
diff --git a/lib/generators/provider/family/templates/item_model.rb.tt b/lib/generators/provider/family/templates/item_model.rb.tt
index 9cfbf1997..9d4a8e437 100644
--- a/lib/generators/provider/family/templates/item_model.rb.tt
+++ b/lib/generators/provider/family/templates/item_model.rb.tt
@@ -27,7 +27,7 @@ class <%= class_name %>Item < ApplicationRecord
 <% end -%>
 
   belongs_to :family
-  has_one_attached :logo
+  has_one_attached :logo, dependent: :purge_later
 
   has_many :<%= file_name %>_accounts, dependent: :destroy
   has_many :accounts, through: :<%= file_name %>_accounts
diff --git a/test/models/account_test.rb b/test/models/account_test.rb
index 8a52192af..5a41f432e 100644
--- a/test/models/account_test.rb
+++ b/test/models/account_test.rb
@@ -1,7 +1,7 @@
 require "test_helper"
 
 class AccountTest < ActiveSupport::TestCase
-  include SyncableInterfaceTest, EntriesTestHelper
+  include SyncableInterfaceTest, EntriesTestHelper, ActiveJob::TestHelper
 
   setup do
     @account = @syncable = accounts(:depository)
@@ -155,4 +155,21 @@ class AccountTest < ActiveSupport::TestCase
     assert @account.taxable?
     assert_not @account.tax_advantaged?
   end
+
+  test "destroying account purges attached logo" do
+    @account.logo.attach(
+      io: StringIO.new("fake-logo-content"),
+      filename: "logo.png",
+      content_type: "image/png"
+    )
+
+    attachment_id = @account.logo.id
+    assert ActiveStorage::Attachment.exists?(attachment_id)
+
+    perform_enqueued_jobs do
+      @account.destroy!
+    end
+
+    assert_not ActiveStorage::Attachment.exists?(attachment_id)
+  end
 end
diff --git a/test/models/pdf_import_test.rb b/test/models/pdf_import_test.rb
index a2491ee1a..37281b5cc 100644
--- a/test/models/pdf_import_test.rb
+++ b/test/models/pdf_import_test.rb
@@ -132,4 +132,21 @@ class PdfImportTest < ActiveSupport::TestCase
     assert_nil @import.account
     assert_not_includes @import.mapping_steps, Import::AccountMapping
   end
+
+  test "destroying import purges attached pdf_file" do
+    @import.pdf_file.attach(
+      io: StringIO.new("fake-pdf-content"),
+      filename: "statement.pdf",
+      content_type: "application/pdf"
+    )
+
+    attachment_id = @import.pdf_file.id
+    assert ActiveStorage::Attachment.exists?(attachment_id)
+
+    perform_enqueued_jobs do
+      @import.destroy!
+    end
+
+    assert_not ActiveStorage::Attachment.exists?(attachment_id)
+  end
 end
diff --git a/test/models/user_test.rb b/test/models/user_test.rb
index a1c0c496e..53b49ed9a 100644
--- a/test/models/user_test.rb
+++ b/test/models/user_test.rb
@@ -1,10 +1,17 @@
 require "test_helper"
 
 class UserTest < ActiveSupport::TestCase
+  include ActiveJob::TestHelper
+
   def setup
     @user = users(:family_admin)
   end
 
+  def teardown
+    clear_enqueued_jobs
+    clear_performed_jobs
+  end
+
   test "should be valid" do
     assert @user.valid?, @user.errors.full_messages.to_sentence
   end
@@ -348,4 +355,45 @@ class UserTest < ActiveSupport::TestCase
     assert_equal :member, User.role_for_new_family_creator(fallback_role: :member)
     assert_equal "custom_role", User.role_for_new_family_creator(fallback_role: "custom_role")
   end
+
+  # ActiveStorage attachment cleanup tests
+  test "purging a user removes attached profile image" do
+    user = users(:family_admin)
+    user.profile_image.attach(
+      io: StringIO.new("profile-image-data"),
+      filename: "profile.png",
+      content_type: "image/png"
+    )
+
+    attachment_id = user.profile_image.id
+    assert ActiveStorage::Attachment.exists?(attachment_id)
+
+    perform_enqueued_jobs do
+      user.purge
+    end
+
+    assert_not User.exists?(user.id)
+    assert_not ActiveStorage::Attachment.exists?(attachment_id)
+  end
+
+  test "purging the last user cascades to remove family and its export attachments" do
+    family = Family.create!(name: "Solo Family", locale: "en", date_format: "%m-%d-%Y", currency: "USD")
+    user = User.create!(family: family, email: "solo@example.com", password: "password123")
+    export = family.family_exports.create!
+    export.export_file.attach(
+      io: StringIO.new("export-data"),
+      filename: "export.zip",
+      content_type: "application/zip"
+    )
+
+    export_attachment_id = export.export_file.id
+    assert ActiveStorage::Attachment.exists?(export_attachment_id)
+
+    perform_enqueued_jobs do
+      user.purge
+    end
+
+    assert_not Family.exists?(family.id)
+    assert_not ActiveStorage::Attachment.exists?(export_attachment_id)
+  end
 end