Queue bounded support and legal email

README.md

@@ -77,7 +77,9 @@ local Codex CLI authenticated with their ChatGPT subscription.
   verified-contact status links, verification-gated support alerts, and audited
   staff queues. Support sends one initial response email and later public-status
   changes through the dedicated Oban `mail` queue; ordinary conversation
-  messages stay in the private inbox and optional push.
+  messages stay in the private inbox and optional push. Content-removal
+  confirmation, receipt, and public decision updates use the same bounded queue,
+  while internal assignment-only changes do not email the submitter.
   Authenticated users can download an allow-listed JSON data export that omits
   password/session/push credentials and counterpart message bodies. A
   moderator-only deletion preflight reports active workflows without performing

docs/operations.md

@@ -1047,11 +1047,13 @@ The worker role consumes `maintenance`, `push`, and `mail`. Configure their
 per-worker limits with `OBAN_MAINTENANCE_CONCURRENCY`,
 `OBAN_PUSH_CONCURRENCY`, and `OBAN_MAIL_CONCURRENCY`; multiplying a value by
 the number of worker replicas gives the configured cluster-wide concurrency
-for that queue. Authentication and mandatory legal-intake confirmations remain
+for that queue. Authentication links remain synchronous because their database
-synchronous. Ordinary support-update email runs in `mail`, so SMTP latency does
+token is committed only when delivery succeeds. Support-contact verification,
-not occupy a web request or the `push` queue. Optional new-case operator alerts
+support updates, content-removal confirmation/receipt/decision messages, and
-also run in `mail`; requester conversation messages do not generate operator
+optional new-case operator alerts run in `mail`, so their SMTP latency does not
-email.
+occupy a web request or the `push` queue. Requester and staff conversation
+messages do not each generate email, and internal assignment-only legal updates
+do not notify the submitter.
 
 After starting the isolated load project, run an explicitly sized experiment:
 

docs/support-and-content-removal.md

@@ -115,6 +115,14 @@ specific review.
   public support contact is verified. Content-removal notification behavior is
   kept separate because those notices can require prompt legal or safety review.
 
+All support-contact and content-removal confirmation, receipt, decision, and
+optional operator-alert messages run through the dedicated Oban `mail` queue.
+Authentication email remains a separate immediate path. A legal operator's
+assignment or other internal-only change does not email the submitter; a public
+status or decision-text change does. Queue uniqueness coalesces an undelivered
+update to the latest persisted case state instead of sending one message for
+each rapid edit.
+
 The alert intentionally excludes the free-text report and reported URLs. The
 full record remains in the protected database queue. If the variable is empty,
 intake and reporter acknowledgement still work, but no operator inbox alert is

docs/verification.md

@@ -30,11 +30,14 @@ results from product limits and unknown production properties.
   response or a later public-status change, while authenticated requesters also
   receive an in-app support update. Ordinary requester and staff conversation
   messages do not each generate email.
-- Optional support email runs through the dedicated Oban `mail` queue, whose
+- Support-contact verification, optional support updates, content-removal
-  default concurrency is one per worker. Fixed-purpose delivery telemetry
+  confirmation/receipt/decision messages, and optional operator alerts run
-  records only the allow-listed purpose and outcome, without email addresses or
+  through the dedicated Oban `mail` queue, whose default concurrency is one per
-  message content. Authentication and content-removal confirmations remain
+  worker. Internal legal assignment-only changes do not email the submitter.
-  transactional email paths by design.
+  Fixed-purpose delivery telemetry records only the allow-listed purpose and
+  outcome, without email addresses or message content. Authentication links
+  remain synchronous by design because their database token is committed only
+  when delivery succeeds.
 - Exact-name inspection after completion found no container or temporary image
   belonging to quality scope `20260812133255-3403320` /
   `wnh_quality_202608121332553403320`.

lib/who_need_help/content_removal.ex

@@ -6,6 +6,7 @@ defmodule WhoNeedHelp.ContentRemoval do
   alias WhoNeedHelp.Accounts
   alias WhoNeedHelp.Accounts.{Scope, User}
   alias WhoNeedHelp.ContentRemoval.{Notice, Notifier}
+  alias WhoNeedHelp.Mail.ContentRemovalEmailWorker
   alias WhoNeedHelp.Pagination
   alias WhoNeedHelp.PublicAccess
   alias WhoNeedHelp.Repo
@@ -63,11 +64,11 @@ defmodule WhoNeedHelp.ContentRemoval do
                    "regime" => to_string(notice.regime),
                    "status" => to_string(notice.status)
                  }
-               ) do
+               ),
+             {:ok, _jobs} <- enqueue_created_emails(notice) do
           {:ok, notice}
         end
       end)
-      |> notify_received()
     end
   end
 
@@ -198,7 +199,13 @@ defmodule WhoNeedHelp.ContentRemoval do
             |> Repo.one()
 
           if notice do
-            with {:ok, notice} <- notice |> Notice.moderation_changeset(attrs) |> Repo.update(),
+            changeset = Notice.moderation_changeset(notice, attrs)
+
+            requester_update? =
+              Ecto.Changeset.changed?(changeset, :status) or
+                Ecto.Changeset.changed?(changeset, :resolution_note)
+
+            with {:ok, notice} <- Repo.update(changeset),
                  {:ok, _audit} <-
                    Trust.audit(
                      moderator.id,
@@ -209,14 +216,15 @@ defmodule WhoNeedHelp.ContentRemoval do
                        "status" => to_string(notice.status),
                        "assigned_to_id" => notice.assigned_to_id
                      }
-                   ) do
+                   ),
-              {:ok, Repo.preload(notice, :assigned_to, force: true)}
+                 {:ok, _job} <- maybe_enqueue_update(notice, requester_update?) do
+              {:ok, {Repo.preload(notice, :assigned_to, force: true), requester_update?}}
             end
           else
             {:error, :not_found}
           end
         end)
-        |> notify_decision()
+        |> normalize_moderation_result()
       end
     else
       false -> {:error, :forbidden}
@@ -224,52 +232,8 @@ defmodule WhoNeedHelp.ContentRemoval do
     end
   end
 
-  defp notify_received({:ok, %Notice{contact_email: email, contact_verified_at: nil} = notice})
+  defp normalize_moderation_result({:ok, {notice, _requester_update?}}), do: {:ok, notice}
-       when is_binary(email) and email != "" do
+  defp normalize_moderation_result(result), do: result
-    case Notifier.deliver_confirmation(notice, confirmation_url(notice)) do
-      {:ok, _metadata} -> mark_acknowledgement_sent(notice)
-      _error -> {:ok, notice}
-    end
-  end
-
-  defp notify_received({:ok, %Notice{contact_email: email} = notice}) when email in [nil, ""],
-    do: notify_operator(notice)
-
-  defp notify_received({:ok, notice}) do
-    result =
-      case Notifier.deliver_received(notice, status_url(notice)) do
-        {:ok, _metadata} -> mark_acknowledgement_sent(notice)
-        _error -> {:ok, notice}
-      end
-
-    case result do
-      {:ok, current} -> notify_operator(current)
-      error -> error
-    end
-  end
-
-  defp notify_received(result), do: result
-
-  defp notify_operator(notice) do
-    _ = Notifier.deliver_operator_alert(notice)
-    {:ok, notice}
-  end
-
-  defp notify_decision({:ok, %Notice{contact_verified_at: nil} = notice}), do: {:ok, notice}
-
-  defp notify_decision({:ok, notice}) do
-    case Notifier.deliver_decision(notice, status_url(notice)) do
-      {:ok, _metadata} ->
-        notice
-        |> Ecto.Changeset.change(decision_sent_at: DateTime.utc_now(:second))
-        |> Repo.update()
-
-      _error ->
-        {:ok, notice}
-    end
-  end
-
-  defp notify_decision(result), do: result
 
   defp verify_contact(%Notice{contact_verified_at: nil} = notice) do
     Repo.transact(fn ->
@@ -287,13 +251,13 @@ defmodule WhoNeedHelp.ContentRemoval do
           {:ok, {current, :already_verified}}
 
         true ->
-          current
+          with {:ok, verified} <-
-          |> Ecto.Changeset.change(contact_verified_at: DateTime.utc_now(:second))
+                 current
-          |> Repo.update()
+                 |> Ecto.Changeset.change(contact_verified_at: DateTime.utc_now(:second))
-          |> then(fn
+                 |> Repo.update(),
-            {:ok, verified} -> {:ok, {verified, :newly_verified}}
+               {:ok, _jobs} <- enqueue_verified_emails(verified) do
-            error -> error
+            {:ok, {verified, :newly_verified}}
-          end)
+          end
       end
     end)
     |> notify_verified_notice()
@@ -302,8 +266,6 @@ defmodule WhoNeedHelp.ContentRemoval do
   defp verify_contact(%Notice{} = notice), do: {:ok, notice}
 
   defp notify_verified_notice({:ok, {notice, :newly_verified}}) do
-    _ = Notifier.deliver_received(notice, status_url(notice))
-    _ = Notifier.deliver_operator_alert(notice)
     {:ok, notice}
   end
 
@@ -325,12 +287,46 @@ defmodule WhoNeedHelp.ContentRemoval do
     Application.fetch_env!(:who_need_help, :public_case_access_max_age_seconds)
   end
 
-  defp mark_acknowledgement_sent(notice) do
+  defp enqueue_email(notice, kind) do
-    notice
+    %{notice_id: notice.id, kind: to_string(kind)}
-    |> Ecto.Changeset.change(acknowledgement_sent_at: DateTime.utc_now(:second))
+    |> ContentRemovalEmailWorker.new()
-    |> Repo.update()
+    |> Oban.insert()
   end
 
+  defp enqueue_created_emails(%Notice{contact_email: email, contact_verified_at: nil} = notice)
+       when is_binary(email) and email != "" do
+    with {:ok, confirmation} <- enqueue_email(notice, :confirmation) do
+      {:ok, [confirmation]}
+    end
+  end
+
+  defp enqueue_created_emails(%Notice{} = notice), do: enqueue_verified_emails(notice)
+
+  defp enqueue_verified_emails(%Notice{} = notice) do
+    with {:ok, received} <- maybe_enqueue_received(notice),
+         {:ok, operator} <- maybe_enqueue_operator(notice) do
+      {:ok, [received, operator]}
+    end
+  end
+
+  defp maybe_enqueue_received(%Notice{contact_email: email} = notice)
+       when is_binary(email) and email != "",
+       do: enqueue_email(notice, :received)
+
+  defp maybe_enqueue_received(%Notice{}), do: {:ok, :no_contact_email}
+
+  defp maybe_enqueue_operator(%Notice{} = notice) do
+    if Notifier.operator_alerts_enabled?(),
+      do: enqueue_email(notice, :operator),
+      else: {:ok, :disabled}
+  end
+
+  defp maybe_enqueue_update(%Notice{contact_verified_at: nil}, _requester_update?),
+    do: {:ok, :contact_not_verified}
+
+  defp maybe_enqueue_update(%Notice{} = notice, true), do: enqueue_email(notice, :update)
+  defp maybe_enqueue_update(%Notice{}, false), do: {:ok, :not_needed}
+
   defp visible_to_staff(query) do
     where(
       query,

lib/who_need_help/content_removal/notifier.ex

@@ -93,6 +93,8 @@ defmodule WhoNeedHelp.ContentRemoval.Notifier do
     end
   end
 
+  def operator_alerts_enabled?, do: match?({:ok, _address}, operator_alert_address())
+
   defp deliver(recipient, subject, body, kind) do
     from = Application.fetch_env!(:who_need_help, :mailer_from)
 

lib/who_need_help/email_delivery.ex

@@ -17,7 +17,6 @@ defmodule WhoNeedHelp.EmailDelivery do
     :content_removal_operator,
     :content_removal_received,
     :content_removal_update,
-    :nearby_alert,
     :support_confirmation,
     :support_operator,
     :support_update

lib/who_need_help/mail/content_removal_email_worker.ex

@@ -0,0 +1,74 @@
+defmodule WhoNeedHelp.Mail.ContentRemovalEmailWorker do
+  @moduledoc false
+
+  use Oban.Worker,
+    queue: :mail,
+    max_attempts: 8,
+    unique: [
+      period: :infinity,
+      fields: [:args, :worker],
+      keys: [:notice_id, :kind],
+      states: :incomplete
+    ]
+
+  alias WhoNeedHelp.ContentRemoval
+  alias WhoNeedHelp.ContentRemoval.{Notice, Notifier}
+  alias WhoNeedHelp.Repo
+
+  @impl Oban.Worker
+  def perform(%Oban.Job{args: %{"notice_id" => notice_id, "kind" => kind}}) do
+    case Repo.get(Notice, notice_id) do
+      nil ->
+        {:cancel, :content_removal_notice_missing}
+
+      %Notice{} = notice ->
+        deliver(notice, kind)
+    end
+  end
+
+  defp deliver(%Notice{contact_verified_at: verified_at}, "confirmation")
+       when not is_nil(verified_at),
+       do: {:cancel, :contact_already_verified}
+
+  defp deliver(%Notice{} = notice, "confirmation") do
+    notice
+    |> Notifier.deliver_confirmation(ContentRemoval.confirmation_url(notice))
+    |> mark_sent(notice, :acknowledgement_sent_at)
+  end
+
+  defp deliver(%Notice{contact_verified_at: nil}, kind) when kind in ["received", "update"],
+    do: {:cancel, :contact_not_verified}
+
+  defp deliver(%Notice{} = notice, "received") do
+    notice
+    |> Notifier.deliver_received(ContentRemoval.status_url(notice))
+    |> mark_sent(notice, :acknowledgement_sent_at)
+  end
+
+  defp deliver(%Notice{} = notice, "update") do
+    notice
+    |> Notifier.deliver_decision(ContentRemoval.status_url(notice))
+    |> mark_sent(notice, :decision_sent_at)
+  end
+
+  defp deliver(%Notice{} = notice, "operator") do
+    case Notifier.deliver_operator_alert(notice) do
+      {:ok, _metadata} -> :ok
+      {:error, reason} -> {:error, reason}
+    end
+  end
+
+  defp deliver(%Notice{}, _kind), do: {:cancel, :unknown_content_removal_email_kind}
+
+  defp mark_sent({:ok, _metadata}, notice, field) do
+    notice
+    |> Ecto.Changeset.change([{field, DateTime.utc_now(:second)}])
+    |> Repo.update()
+    |> case do
+      {:ok, _notice} -> :ok
+      {:error, reason} -> {:error, reason}
+    end
+  end
+
+  defp mark_sent({:error, reason}, _notice, _field), do: {:error, reason}
+end

lib/who_need_help/mail/support_confirmation_worker.ex

@@ -0,0 +1,34 @@
+defmodule WhoNeedHelp.Mail.SupportConfirmationWorker do
+  @moduledoc false
+
+  use Oban.Worker,
+    queue: :mail,
+    max_attempts: 8,
+    unique: [
+      period: :infinity,
+      fields: [:args, :worker],
+      keys: [:request_id],
+      states: :incomplete
+    ]
+
+  alias WhoNeedHelp.Repo
+  alias WhoNeedHelp.Support
+  alias WhoNeedHelp.Support.{Notifier, SupportRequest}
+
+  @impl Oban.Worker
+  def perform(%Oban.Job{args: %{"request_id" => request_id}}) do
+    case Repo.get(SupportRequest, request_id) do
+      nil ->
+        {:cancel, :support_request_missing}
+
+      %SupportRequest{contact_verified_at: verified_at} when not is_nil(verified_at) ->
+        {:cancel, :contact_already_verified}
+
+      %SupportRequest{} = request ->
+        case Notifier.deliver_confirmation(request, Support.confirmation_url(request)) do
+          {:ok, _metadata} -> :ok
+          {:error, reason} -> {:error, reason}
+        end
+    end
+  end
+end

lib/who_need_help/support.ex

@@ -6,7 +6,13 @@ defmodule WhoNeedHelp.Support do
   alias WhoNeedHelp.Accounts
   alias WhoNeedHelp.Accounts.DataLifecycle
   alias WhoNeedHelp.Accounts.{Scope, User}
-  alias WhoNeedHelp.Mail.{SupportOperatorAlertWorker, SupportUpdateWorker}
+
+  alias WhoNeedHelp.Mail.{
+    SupportConfirmationWorker,
+    SupportOperatorAlertWorker,
+    SupportUpdateWorker
+  }
+
   alias WhoNeedHelp.Notifications
   alias WhoNeedHelp.Pagination
   alias WhoNeedHelp.PublicAccess
@@ -70,14 +76,14 @@ defmodule WhoNeedHelp.Support do
                    request.status,
                    user && user.id,
                    :requester
-                 ) do
+                 ),
+               {:ok, _job} <- enqueue_created_email(request) do
             {:ok, request}
           end
         end)
 
       result
       |> resolve_duplicate_submission(fingerprint)
-      |> notify_created()
       |> broadcast_request_update()
     end
   end
@@ -257,14 +263,14 @@ defmodule WhoNeedHelp.Support do
                        "status" => to_string(request.status),
                        "assigned_to_id" => request.assigned_to_id
                      }
-                   ) do
+                   ),
-              {:ok,
+                 update = %{
-               {preload_conversation(request),
+                   audit_id: audit.id,
-                %{
+                   message_added: match?(%ConversationMessage{}, message),
-                  audit_id: audit.id,
+                   status_changed: previous_status != request.status
-                  message_added: match?(%ConversationMessage{}, message),
+                 },
-                  status_changed: previous_status != request.status
+                 {:ok, _job} <- maybe_enqueue_support_email(request, update) do
-                }}}
+              {:ok, {preload_conversation(request), update}}
             end
           else
             {:error, :not_found}
@@ -406,18 +412,13 @@ defmodule WhoNeedHelp.Support do
     end
   end
 
-  defp notify_created({:ok, {request, :pending_verification}}) do
+  defp enqueue_created_email(%SupportRequest{contact_verified_at: nil} = request) do
-    _ = Notifier.deliver_confirmation(request, confirmation_url(request))
+    request.id
-    {:ok, request}
+    |> then(&SupportConfirmationWorker.new(%{request_id: &1}))
+    |> Oban.insert()
   end
 
-  defp notify_created({:ok, {request, :verified}}) do
+  defp enqueue_created_email(%SupportRequest{} = request), do: enqueue_operator_alert(request)
-    _ = enqueue_operator_alert(request)
-    {:ok, request}
-  end
-
-  defp notify_created({:ok, {request, :duplicate}}), do: {:ok, request}
-  defp notify_created(result), do: result
 
   defp notify_decision({:ok, {%SupportRequest{contact_verified_at: nil} = request, _update}}),
     do: {:ok, request}
@@ -427,10 +428,6 @@ defmodule WhoNeedHelp.Support do
       notify_requester_in_app(request, update)
     end
 
-    if support_email_needed?(request, update) do
-      _ = enqueue_support_email(request)
-    end
-
     {:ok, request}
   end
 
@@ -493,7 +490,8 @@ defmodule WhoNeedHelp.Support do
                    "support_request.contact_verified",
                    "support_request",
                    verified.id
-                 ) do
+                 ),
+               {:ok, _job} <- enqueue_operator_alert(verified) do
             {:ok, {verified, :newly_verified}}
           end
       end
@@ -504,8 +502,6 @@ defmodule WhoNeedHelp.Support do
   defp verify_contact(%SupportRequest{} = request), do: {:ok, request}
 
   defp notify_verified_request({:ok, {request, :newly_verified}}) do
-    _ = enqueue_operator_alert(request)
-
     event = {:support_request_updated, request.id}
     Phoenix.PubSub.broadcast(WhoNeedHelp.PubSub, request_topic(request.id), event)
     Phoenix.PubSub.broadcast(WhoNeedHelp.PubSub, @staff_topic, event)
@@ -538,6 +534,14 @@ defmodule WhoNeedHelp.Support do
     update.status_changed or (update.message_added and is_nil(request.response_sent_at))
   end
 
+  defp maybe_enqueue_support_email(request, update) do
+    if support_email_needed?(request, update) do
+      enqueue_support_email(request)
+    else
+      {:ok, :not_needed}
+    end
+  end
+
   defp enqueue_support_email(request) do
     request.id
     |> then(&SupportUpdateWorker.new(%{request_id: &1}))
@@ -757,15 +761,14 @@ defmodule WhoNeedHelp.Support do
   end
 
   defp resolve_duplicate_submission({:ok, request}, _fingerprint) do
-    outcome = if request.contact_verified_at, do: :verified, else: :pending_verification
+    {:ok, request}
-    {:ok, {request, outcome}}
   end
 
   defp resolve_duplicate_submission({:error, %Ecto.Changeset{} = changeset} = error, fingerprint)
        when is_binary(fingerprint) do
     if duplicate_fingerprint_error?(changeset) do
       case Repo.get_by(SupportRequest, public_submission_fingerprint: fingerprint) do
-        %SupportRequest{} = request -> {:ok, {request, :duplicate}}
+        %SupportRequest{} = request -> {:ok, request}
         nil -> error
       end
     else

test/who_need_help/support_and_content_removal_test.exs

@@ -7,7 +7,14 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
 
   alias WhoNeedHelp.{Catalog, ContentRemoval, Help, Repo, Support}
   alias WhoNeedHelp.ContentRemoval.Notice
-  alias WhoNeedHelp.Mail.{SupportOperatorAlertWorker, SupportUpdateWorker}
+
+  alias WhoNeedHelp.Mail.{
+    ContentRemovalEmailWorker,
+    SupportConfirmationWorker,
+    SupportOperatorAlertWorker,
+    SupportUpdateWorker
+  }
+
   alias WhoNeedHelp.Notifications.Notification
   alias WhoNeedHelp.Support.{ConversationMessage, StatusEvent, SupportRequest}
   alias WhoNeedHelp.Trust.AuditEvent
@@ -27,6 +34,14 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
     assert is_binary(request.public_submission_fingerprint)
     assert is_nil(request.contact_verified_at)
 
+    assert_enqueued(
+      worker: SupportConfirmationWorker,
+      queue: :mail,
+      args: %{"request_id" => request.id}
+    )
+
+    assert :ok = perform_job(SupportConfirmationWorker, %{"request_id" => request.id})
+
     test_pid = self()
 
     assert_email_sent(fn email ->
@@ -103,6 +118,8 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
                  "Please review the moderation decision identified in my account notice."
              })
 
+    assert :ok = perform_job(SupportConfirmationWorker, %{"request_id" => request.id})
+
     assert_email_sent(fn email ->
       email.to == [{"", "appeal@example.com"}] and
         email.reply_to == {"", "support@example.com"} and
@@ -179,6 +196,7 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
     }
 
     assert {:ok, first} = Support.create_request(nil, attrs)
+    assert :ok = perform_job(SupportConfirmationWorker, %{"request_id" => first.id})
     assert_email_sent()
 
     assert {:ok, duplicate} =
@@ -386,11 +404,98 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
 
     assert {:ok, assigned_notice} =
              ContentRemoval.moderate(operator_scope, notice.id, %{
-               "status" => "reviewing",
+               "status" => "open",
                "assigned_to_id" => legal_assignee.id
              })
 
     assert assigned_notice.assigned_to_id == legal_assignee.id
+
+    refute_enqueued(
+      worker: ContentRemovalEmailWorker,
+      args: %{"notice_id" => notice.id, "kind" => "update"}
+    )
+  end
+
+  test "content-removal mail is queued and internal assignment does not notify the submitter" do
+    requester = user_fixture()
+    assert_email_sent()
+    legal_operator = staff_user_fixture([:legal], display_name: "Legal operator")
+    assert_email_sent()
+    operator_scope = user_scope_fixture(legal_operator)
+
+    assert {:ok, notice} =
+             ContentRemoval.create_notice(user_scope_fixture(requester), :general, %{
+               "category" => "privacy_violation",
+               "submitter_name" => "Verified submitter",
+               "relationship" => "self",
+               "content_locations" => "https://example.test/requests/queued-legal-mail",
+               "explanation" =>
+                 "This notice verifies bounded asynchronous legal-notice email delivery.",
+               "electronic_signature" => "Verified submitter",
+               "good_faith" => "true",
+               "accurate_complete" => "true"
+             })
+
+    assert_enqueued(
+      worker: ContentRemovalEmailWorker,
+      queue: :mail,
+      args: %{"notice_id" => notice.id, "kind" => "received"}
+    )
+
+    refute_receive {:email, _synchronous_received_email}, 50
+
+    assert :ok =
+             perform_job(ContentRemovalEmailWorker, %{
+               "notice_id" => notice.id,
+               "kind" => "received"
+             })
+
+    assert Repo.reload!(notice).acknowledgement_sent_at
+
+    assert_email_sent(fn email ->
+      email.subject =~ notice.reference and email.text_body =~ "We received removal notice"
+    end)
+
+    assert {:ok, assigned} =
+             ContentRemoval.moderate(operator_scope, notice.id, %{
+               "status" => "open",
+               "assigned_to_id" => legal_operator.id
+             })
+
+    assert assigned.assigned_to_id == legal_operator.id
+
+    refute_enqueued(
+      worker: ContentRemovalEmailWorker,
+      args: %{"notice_id" => notice.id, "kind" => "update"}
+    )
+
+    assert {:ok, updated} =
+             ContentRemoval.moderate(operator_scope, notice.id, %{
+               "status" => "needs_information",
+               "assigned_to_id" => legal_operator.id,
+               "resolution_note" => "Please provide one exact public URL for review."
+             })
+
+    assert updated.status == :needs_information
+
+    assert_enqueued(
+      worker: ContentRemovalEmailWorker,
+      queue: :mail,
+      args: %{"notice_id" => notice.id, "kind" => "update"}
+    )
+
+    assert :ok =
+             perform_job(ContentRemovalEmailWorker, %{
+               "notice_id" => notice.id,
+               "kind" => "update"
+             })
+
+    assert Repo.reload!(updated).decision_sent_at
+
+    assert_email_sent(fn email ->
+      email.subject =~ "removal notice update" and
+        email.text_body =~ "Please provide one exact public URL for review."
+    end)
   end
 
   test "requester replies reopen a finished case and preserve the full conversation history" do
@@ -515,6 +620,18 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
     assert notice.response_due_at
     assert is_nil(notice.contact_verified_at)
 
+    assert_enqueued(
+      worker: ContentRemovalEmailWorker,
+      queue: :mail,
+      args: %{"notice_id" => notice.id, "kind" => "confirmation"}
+    )
+
+    assert :ok =
+             perform_job(ContentRemovalEmailWorker, %{
+               "notice_id" => notice.id,
+               "kind" => "confirmation"
+             })
+
     assert_email_sent(fn email ->
       email.subject =~ "Confirm Who Need Help removal notice" and
         email.text_body =~ notice.reference and
@@ -538,6 +655,12 @@ defmodule WhoNeedHelp.SupportAndContentRemovalTest do
 
     assert verified.contact_verified_at
 
+    assert_enqueued(
+      worker: ContentRemovalEmailWorker,
+      queue: :mail,
+      args: %{"notice_id" => notice.id, "kind" => "received"}
+    )
+
     assert Enum.map(ContentRemoval.paginate_for_staff(moderator_scope).entries, & &1.id) == [
              notice.id
            ]

test/who_need_help_web/controllers/support_controller_test.exs

@@ -1,11 +1,13 @@
 defmodule WhoNeedHelpWeb.SupportControllerTest do
   use WhoNeedHelpWeb.ConnCase, async: false
+  use Oban.Testing, repo: WhoNeedHelp.Repo
 
   import Phoenix.LiveViewTest
   import WhoNeedHelp.AccountsFixtures
   import Swoosh.TestAssertions
 
   alias WhoNeedHelp.Repo
+  alias WhoNeedHelp.Mail.{ContentRemovalEmailWorker, SupportConfirmationWorker}
   alias WhoNeedHelp.Support.SupportRequest
 
   describe "public support and removal intake" do
@@ -66,6 +68,18 @@ defmodule WhoNeedHelpWeb.SupportControllerTest do
       assert location =~ "/support/received?reference=SUP-"
       refute location =~ "token="
 
+      request = Repo.get_by!(SupportRequest, contact_email: "person@example.com")
+
+      assert_enqueued(
+        worker: SupportConfirmationWorker,
+        queue: :mail,
+        args: %{"request_id" => request.id}
+      )
+
+      refute_receive {:email, _synchronous_confirmation}, 50
+
+      assert :ok = perform_job(SupportConfirmationWorker, %{"request_id" => request.id})
+
       assert_email_sent(fn email ->
         email.to == [{"", "person@example.com"}] and
           email.subject =~ "Confirm Who Need Help support request"
@@ -134,6 +148,26 @@ defmodule WhoNeedHelpWeb.SupportControllerTest do
       location = redirected_to(conn)
       assert location =~ "/legal/content-removal/received?reference=REM-"
       refute location =~ "token="
+
+      notice =
+        Repo.get_by!(WhoNeedHelp.ContentRemoval.Notice,
+          contact_email: "affected@example.com"
+        )
+
+      assert_enqueued(
+        worker: ContentRemovalEmailWorker,
+        queue: :mail,
+        args: %{"notice_id" => notice.id, "kind" => "confirmation"}
+      )
+
+      refute_receive {:email, _synchronous_confirmation}, 50
+
+      assert :ok =
+               perform_job(ContentRemovalEmailWorker, %{
+                 "notice_id" => notice.id,
+                 "kind" => "confirmation"
+               })
+
       assert_email_sent()
     end