diff --git a/lib/towerops/llm/network_snapshot.ex b/lib/towerops/llm/network_snapshot.ex
index 0de2c180..b89d07d6 100644
--- a/lib/towerops/llm/network_snapshot.ex
+++ b/lib/towerops/llm/network_snapshot.ex
@@ -263,11 +263,29 @@ defmodule Towerops.LLM.NetworkSnapshot do
     %{high_utilization: high}
   end
 
-  defp build_gaiia(_organization_id) do
-    # The reconciliation worker has its own cache; rather than recompute
-    # here we surface only the *count* of currently active reconciliation
-    # findings (cheap query) and let the LLM see them as existing insights.
-    %{untracked: 0, ghosts: 0, mismatches: 0}
+  defp build_gaiia(organization_id) do
+    rows =
+      Insight
+      |> where([i], i.organization_id == ^organization_id)
+      |> where([i], i.type == "reconciliation_finding" and i.status == "active")
+      |> select([i], %{
+        finding_type: fragment("?->>'finding_type'", i.metadata),
+        item_count: fragment("(?->>'count')::int", i.metadata)
+      })
+      |> Repo.all()
+
+    %{
+      untracked: item_count_for(rows, "untracked"),
+      ghosts: item_count_for(rows, "ghost"),
+      mismatches: item_count_for(rows, "mismatch")
+    }
+  end
+
+  defp item_count_for(rows, type) do
+    Enum.find_value(rows, 0, fn
+      %{finding_type: ^type, item_count: count} -> count
+      _ -> nil
+    end)
   end
 
   defp build_agents(organization_id) do
diff --git a/lib/towerops/workers/ai_network_insight_worker.ex b/lib/towerops/workers/ai_network_insight_worker.ex
index 5e431816..49e7c7e6 100644
--- a/lib/towerops/workers/ai_network_insight_worker.ex
+++ b/lib/towerops/workers/ai_network_insight_worker.ex
@@ -32,14 +32,19 @@ defmodule Towerops.Workers.AiNetworkInsightWorker do
 
   @impl Oban.Worker
   def perform(%Oban.Job{}) do
-    Repo.transaction(fn ->
-      Organization
-      |> select([o], o.id)
-      |> Repo.stream()
-      |> Enum.each(&process_organization/1)
-    end)
+    case Repo.transaction(fn ->
+           Organization
+           |> select([o], o.id)
+           |> Repo.stream()
+           |> Enum.each(&process_organization/1)
+         end) do
+      {:ok, _} ->
+        :ok
 
-    :ok
+      {:error, reason} ->
+        Logger.error("AI network insight transaction failed: #{inspect(reason)}")
+        {:error, reason}
+    end
   end
 
   defp process_organization(organization_id) do
@@ -56,7 +61,7 @@ defmodule Towerops.Workers.AiNetworkInsightWorker do
         :ok
 
       {:error, reason} ->
-        Logger.warning("AI network insight failed for org #{organization_id}: #{inspect(reason)}")
+        Logger.error("AI network insight LLM call failed for org #{organization_id}: #{inspect(reason)}")
         :ok
     end
   rescue
@@ -93,7 +98,7 @@ defmodule Towerops.Workers.AiNetworkInsightWorker do
         :ok
 
       {:error, changeset} ->
-        Logger.warning("Failed to persist ai_observation: #{inspect(changeset.errors)}")
+        Logger.error("Failed to persist ai_observation: #{inspect(changeset.errors)}")
         :ok
     end
   end
@@ -106,15 +111,19 @@ defmodule Towerops.Workers.AiNetworkInsightWorker do
   end
 
   defp record_usage(organization_id, response, model) do
-    _ =
-      Usage.record(%{
-        organization_id: organization_id,
-        model: model,
-        purpose: "network_insight",
-        prompt_tokens: Map.get(response, :prompt_tokens) || 0,
-        completion_tokens: Map.get(response, :completion_tokens) || 0
-      })
+    case Usage.record(%{
+           organization_id: organization_id,
+           model: model,
+           purpose: "network_insight",
+           prompt_tokens: Map.get(response, :prompt_tokens) || 0,
+           completion_tokens: Map.get(response, :completion_tokens) || 0
+         }) do
+      {:ok, _} ->
+        :ok
 
-    :ok
+      {:error, changeset} ->
+        Logger.error("Failed to record LLM usage: #{inspect(changeset.errors)}")
+        :ok
+    end
   end
 end
diff --git a/lib/towerops/workers/insight_llm_enrichment_worker.ex b/lib/towerops/workers/insight_llm_enrichment_worker.ex
index bbf3ddb7..155a88ed 100644
--- a/lib/towerops/workers/insight_llm_enrichment_worker.ex
+++ b/lib/towerops/workers/insight_llm_enrichment_worker.ex
@@ -34,24 +34,33 @@ defmodule Towerops.Workers.InsightLlmEnrichmentWorker do
     case LLM.complete(messages, max_tokens: 400, temperature: 0.2) do
       {:ok, %{content: content, model: model} = response} ->
         {:ok, parsed} = InsightPrompt.parse(content)
-        {:ok, _} = Insights.apply_llm_enrichment(insight, parsed, model)
 
-        # Token-usage tracking lives in its own table — every LLM
-        # consumer in the codebase records here so the per-org daily
-        # cost is queryable in one place.
-        _ =
-          Usage.record(%{
-            organization_id: insight.organization_id,
-            model: model,
-            purpose: "insight_enrichment",
-            prompt_tokens: Map.get(response, :prompt_tokens) || 0,
-            completion_tokens: Map.get(response, :completion_tokens) || 0
-          })
+        case Insights.apply_llm_enrichment(insight, parsed, model) do
+          {:ok, _} ->
+            record_usage(insight.organization_id, response, model)
 
-        :ok
+          {:error, changeset} ->
+            Logger.error("Failed to persist LLM enrichment for insight #{insight.id}: #{inspect(changeset.errors)}")
+        end
 
       {:error, reason} ->
-        Logger.warning("LLM enrichment failed for insight #{insight.id}: #{inspect(reason)}")
+        Logger.error("LLM enrichment failed for insight #{insight.id}: #{inspect(reason)}")
+    end
+  end
+
+  defp record_usage(organization_id, response, model) do
+    case Usage.record(%{
+           organization_id: organization_id,
+           model: model,
+           purpose: "insight_enrichment",
+           prompt_tokens: Map.get(response, :prompt_tokens) || 0,
+           completion_tokens: Map.get(response, :completion_tokens) || 0
+         }) do
+      {:ok, _} ->
+        :ok
+
+      {:error, changeset} ->
+        Logger.error("Failed to record LLM usage: #{inspect(changeset.errors)}")
         :ok
     end
   end
diff --git a/lib/towerops_web/live/insights_live/index.ex b/lib/towerops_web/live/insights_live/index.ex
index 3dbd4744..93c43d94 100644
--- a/lib/towerops_web/live/insights_live/index.ex
+++ b/lib/towerops_web/live/insights_live/index.ex
@@ -107,16 +107,22 @@ defmodule ToweropsWeb.InsightsLive.Index do
   @impl true
   def handle_event("regenerate_insights", _params, socket) do
     if Scope.superuser?(socket.assigns.current_scope) do
-      Enum.each(@regeneration_workers, fn worker ->
-        %{} |> worker.new() |> Oban.insert()
-      end)
+      {ok_count, fail_count} = insert_regeneration_jobs()
 
-      {:noreply,
-       put_flash(
-         socket,
-         :info,
-         t("Insight regeneration queued. New insights will appear shortly.")
-       )}
+      flash =
+        if fail_count == 0 do
+          {:info, t("Insight regeneration queued. New insights will appear shortly.")}
+        else
+          {:error,
+           "%{ok} worker queued, %{fail} worker failed to queue. Check logs."
+           |> ngettext(
+             "%{ok} workers queued, %{fail} workers failed to queue. Check logs.",
+             ok_count
+           )
+           |> then(&Gettext.dngettext(ToweropsWeb.Gettext, "", &1, &1, ok_count: ok_count, fail: fail_count))}
+        end
+
+      {:noreply, put_flash(socket, elem(flash, 0), elem(flash, 1))}
     else
       {:noreply, put_flash(socket, :error, t("Not authorized."))}
     end
@@ -139,6 +145,21 @@ defmodule ToweropsWeb.InsightsLive.Index do
     end
   end
 
+  defp insert_regeneration_jobs do
+    require Logger
+
+    Enum.reduce(@regeneration_workers, {0, 0}, fn worker, {ok, fail} ->
+      case %{} |> worker.new() |> Oban.insert() do
+        {:ok, _} ->
+          {ok + 1, fail}
+
+        {:error, changeset} ->
+          Logger.error("Failed to insert #{inspect(worker)}: #{inspect(changeset.errors)}")
+          {ok, fail + 1}
+      end
+    end)
+  end
+
   defp load_insights(socket) do
     org_id = socket.assigns.organization.id
     opts = [status: socket.assigns.filter_status]