diff --git a/src/lib/agent/runner/sequence/orchestrator/__tests__/optional-tasks.test.ts b/src/lib/agent/runner/sequence/orchestrator/__tests__/optional-tasks.test.ts
index 85e130bce..1e4e2d7f4 100644
--- a/src/lib/agent/runner/sequence/orchestrator/__tests__/optional-tasks.test.ts
+++ b/src/lib/agent/runner/sequence/orchestrator/__tests__/optional-tasks.test.ts
@@ -8,7 +8,10 @@ vi.mock('@utils/analytics', () => ({
 }));
 
 import { QueueStore } from '@lib/agent/runner/sequence/orchestrator/queue';
-import { drainVerdict } from '@lib/agent/runner/sequence/orchestrator/orchestrator-runner';
+import {
+  describeDrainFailure,
+  drainVerdict,
+} from '@lib/agent/runner/sequence/orchestrator/orchestrator-runner';
 
 describe('drainVerdict', () => {
   let dir: string;
@@ -52,5 +55,47 @@ describe('drainVerdict', () => {
     const v = drainVerdict(store.list());
     expect(v.requiredFailedTypes).toEqual(['install']);
     expect(v.blocked).toBe(1);
+    expect(v.blockedTypes).toEqual(['report']);
+  });
+
+  it('names a step the user accepted that never became runnable', () => {
+    const install = store.enqueue({ type: 'install' });
+    store.enqueue({
+      type: 'warehouse',
+      optional: true,
+      dependsOn: [install.id],
+    });
+    finish(install.id, false);
+
+    expect(drainVerdict(store.list()).blockedTypes).toEqual(['warehouse']);
+  });
+});
+
+describe('describeDrainFailure', () => {
+  it('names the failure and the steps it stopped', () => {
+    expect(
+      describeDrainFailure({
+        requiredFailedTypes: ['install'],
+        blockedTypes: ['warehouse', 'report'],
+      }),
+    ).toBe('the install step failed, so the warehouse, report steps never ran');
+  });
+
+  it('names blocked steps when nothing failed outright', () => {
+    expect(
+      describeDrainFailure({
+        requiredFailedTypes: [],
+        blockedTypes: ['warehouse'],
+      }),
+    ).toBe('the warehouse step never ran');
+  });
+
+  it('names the failure alone when nothing was left pending', () => {
+    expect(
+      describeDrainFailure({
+        requiredFailedTypes: ['report'],
+        blockedTypes: [],
+      }),
+    ).toBe('the report step failed');
   });
 });
diff --git a/src/lib/agent/runner/sequence/orchestrator/orchestrator-runner.ts b/src/lib/agent/runner/sequence/orchestrator/orchestrator-runner.ts
index 8778431ad..fcbf4c15b 100644
--- a/src/lib/agent/runner/sequence/orchestrator/orchestrator-runner.ts
+++ b/src/lib/agent/runner/sequence/orchestrator/orchestrator-runner.ts
@@ -370,8 +370,10 @@ export function drainVerdict(tasks: readonly QueuedTask[]): {
   requiredFailedTypes: string[];
   optionalFailedTypes: string[];
   blocked: number;
+  blockedTypes: string[];
 } {
   const failed = tasks.filter((t) => t.status === TaskStatus.Failed);
+  const pending = tasks.filter((t) => t.status === TaskStatus.Pending);
   return {
     requiredFailedTypes: failed
       .filter((t) => t.optional !== true)
@@ -379,10 +381,37 @@ export function drainVerdict(tasks: readonly QueuedTask[]): {
     optionalFailedTypes: failed
       .filter((t) => t.optional === true)
       .map((t) => t.type),
-    blocked: tasks.filter((t) => t.status === TaskStatus.Pending).length,
+    blocked: pending.length,
+    blockedTypes: pending.map((t) => t.type),
   };
 }
 
+/**
+ * The one-line "what went wrong" the abort message leads with.
+ *
+ * Both halves are named. A drain that ends with work still pending used to
+ * report only how many steps never ran, which is the least useful fact about
+ * them: a user who agreed to connect their data sources and then read that
+ * "2 steps never ran" had no way to tell whether that step was one of them.
+ */
+export function describeDrainFailure(verdict: {
+  requiredFailedTypes: string[];
+  blockedTypes: string[];
+}): string {
+  const parts: string[] = [];
+  if (verdict.requiredFailedTypes.length > 0) {
+    parts.push(`the ${verdict.requiredFailedTypes.join(', ')} step failed`);
+  }
+  if (verdict.blockedTypes.length > 0) {
+    parts.push(
+      `the ${verdict.blockedTypes.join(', ')} step${
+        verdict.blockedTypes.length === 1 ? '' : 's'
+      } never ran`,
+    );
+  }
+  return parts.join(', so ');
+}
+
 /** How many tasks deep in the graph a task sits — 0 when it depends on nothing. */
 function graphDepth(
   task: QueuedTask,
@@ -1155,11 +1184,23 @@ export async function runOrchestrator(
   // A failed optional task is exempt: reported per-task, never run-failing.
   const verdict = drainVerdict(store.list());
   const blocked = verdict.blocked;
+  // A pending task at this point never ran and never will — its dependency
+  // failed. No transition fires for it, so without this the step leaves no
+  // terminal event at all: a step the user was offered and accepted simply
+  // drops out of the funnel. The queue itself is left alone, because the run
+  // cache is already wiped by here and writing to it would recreate the folder
+  // the cleanup just removed.
+  for (const task of store.list()) {
+    if (task.status !== TaskStatus.Pending) continue;
+    analytics.wizardCapture('orchestrator task blocked', {
+      type: task.type,
+      optional: task.optional === true,
+      failed_types: verdict.requiredFailedTypes.join(',') || 'none',
+    });
+  }
   if (verdict.requiredFailedTypes.length > 0 || blocked > 0) {
     const failedTypes = verdict.requiredFailedTypes.join(', ');
-    const whatFailed = failedTypes
-      ? `the ${failedTypes} step failed`
-      : `${blocked} steps never ran`;
+    const whatFailed = describeDrainFailure(verdict);
     // A grant narrowed at login is the one failure cause the user can fix
     // alone — lead with the fix, and only fall back to the report-a-bug line
     // when trying again doesn't work.