diff --git a/desktop/src/features/workflows/triggerOperations.test.mjs b/desktop/src/features/workflows/triggerOperations.test.mjs
index 7fb669afd8..fb2f3e3352 100644
--- a/desktop/src/features/workflows/triggerOperations.test.mjs
+++ b/desktop/src/features/workflows/triggerOperations.test.mjs
@@ -58,6 +58,7 @@ test("production owner retains exact signed payload after committed response los
   release();
   await assert.rejects(first, /response lost/);
   assert.equal(owner.state(key).status, "error");
+  assert.equal(owner.state(key).failurePhase, "submit");
   const result = await owner.run("workflow", scope);
   assert.equal(result.runId, "run-1");
   assert.equal(prepared, 1);
@@ -119,6 +120,10 @@ test("preflight rejection retries preparation without inventing a submitted even
       assert.fail("preflight failure must not publish"),
   });
   await assert.rejects(owner.run("workflow", scope), /stale revision/);
+  assert.equal(
+    owner.state(owner.key("workflow", scope)).failurePhase,
+    "prepare",
+  );
   await assert.rejects(owner.run("workflow", scope), /stale revision/);
   assert.equal(tries, 2);
 });
diff --git a/desktop/src/features/workflows/triggerOperations.ts b/desktop/src/features/workflows/triggerOperations.ts
index 55670288a3..1d2fd1676b 100644
--- a/desktop/src/features/workflows/triggerOperations.ts
+++ b/desktop/src/features/workflows/triggerOperations.ts
@@ -8,6 +8,7 @@ import type { RelayEvent, TriggerWorkflowResponse } from "@/shared/api/types";
 export type TriggerState = {
   status: "idle" | "pending" | "error" | "success";
   error?: string;
+  failurePhase?: "prepare" | "submit";
   result?: TriggerWorkflowResponse;
 };
 const idle: TriggerState = { status: "idle" };
@@ -61,7 +62,8 @@ export class WorkflowTriggerOperations {
     let op = this.operations.get(key);
     if (op?.inFlight) return op.inFlight;
     // A settled success means the next explicit Trigger is a distinct run.
-    // An error means Retry of the same event unless the user explicitly opts out.
+    // Submission errors retry the same event unless the user explicitly opts out.
+    // Preparation errors have not published anything and may prepare again.
     if (!op || newRun || op.state.status === "success") {
       if (!op && this.operations.size >= 256) {
         for (const [oldKey, old] of this.operations) {
@@ -99,6 +101,7 @@ export class WorkflowTriggerOperations {
         operation.state = {
           status: "error",
           error: error instanceof Error ? error.message : String(error),
+          failurePhase: operation.event ? "submit" : "prepare",
         };
         throw error;
       } finally {
diff --git a/desktop/src/features/workflows/ui/WorkflowTriggerFeedback.tsx b/desktop/src/features/workflows/ui/WorkflowTriggerFeedback.tsx
index b915299728..0389ac5cc7 100644
--- a/desktop/src/features/workflows/ui/WorkflowTriggerFeedback.tsx
+++ b/desktop/src/features/workflows/ui/WorkflowTriggerFeedback.tsx
@@ -34,6 +34,19 @@ export function WorkflowTriggerFeedback({
         Run created: {state.result?.runId}
       </p>
     );
+  if (state.failurePhase === "prepare")
+    return (
+      <div
+        role="alert"
+        className="pointer-events-auto space-y-2 text-xs text-destructive"
+      >
+        <p>Workflow run was not started. {state.error}</p>
+        <p>Retry prepares a new request before submitting it.</p>
+        <Button size="sm" variant="outline" onClick={onRetry}>
+          Retry trigger
+        </Button>
+      </div>
+    );
   return (
     <div
       role="alert"
diff --git a/desktop/src/features/workflows/ui/workflowTriggerFeedback.test.mjs b/desktop/src/features/workflows/ui/workflowTriggerFeedback.test.mjs
index 5621fec457..8e45b0bed1 100644
--- a/desktop/src/features/workflows/ui/workflowTriggerFeedback.test.mjs
+++ b/desktop/src/features/workflows/ui/workflowTriggerFeedback.test.mjs
@@ -45,7 +45,7 @@ after(() => dom.window.close());
 // Actual card + detail hook + IPC adapters. Unlike the former invocation-count
 // assertion, this peer signs and commits an event, loses the response, then
 // verifies the exact retry bytes and returns the same persisted run identity.
-test("card/detail share pending, accessible error/retry and confirmed-only success animation", async () => {
+test("card/detail distinguish preparation from ambiguous submission and animate only confirmed success", async () => {
   const keys = generateSecretKey();
   const pubkey = getPublicKey(keys);
   localStorage.setItem(
@@ -92,6 +92,7 @@ test("card/detail share pending, accessible error/retry and confirmed-only succe
       if (command === "get_run_approvals") return { approvals: [] };
       if (command === "prepare_workflow_trigger") {
         prepares++;
+        if (prepares === 1) throw new Error("revision lookup failed");
         assert.equal(args.expectedRelayUrl, "wss://a.example");
         assert.equal(args.expectedSignerPubkey, pubkey);
         return finalizeEvent(
@@ -196,6 +197,26 @@ test("card/detail share pending, accessible error/retry and confirmed-only succe
     fireEvent.click(
       rendered.getByRole("menuitem", { name: "Trigger", exact: true }),
     );
+    await waitFor(() =>
+      assert.match(
+        card.getByRole("alert").textContent,
+        /revision lookup failed/,
+      ),
+    );
+    for (const surface of [card, detail]) {
+      const text = surface.getByRole("alert").textContent;
+      assert.match(text, /Workflow run was not started/);
+      assert.doesNotMatch(text, /may already exist|same signed request/);
+      assert.equal(
+        surface.queryByRole("button", { name: "Start a distinct run…" }),
+        null,
+      );
+    }
+    assert.equal(posts.length, 0, "preparation failure cannot publish");
+    assert.equal(stack.firstChild, originalTile);
+    fireEvent.click(
+      card.getByRole("button", { name: "Retry trigger", exact: true }),
+    );
     await waitFor(() => assert.equal(posts.length, 1));
     assert.match(card.getByRole("status").textContent, /Triggering/);
     assert.equal(
@@ -226,6 +247,13 @@ test("card/detail share pending, accessible error/retry and confirmed-only succe
       ),
     );
     assert.match(detail.getByRole("alert").textContent, /same signed request/);
+    for (const surface of [card, detail]) {
+      assert.doesNotMatch(
+        surface.getByRole("alert").textContent,
+        /was not started/,
+      );
+      assert.ok(surface.getByRole("button", { name: "Start a distinct run…" }));
+    }
     assert.equal(
       stack.firstChild,
       originalTile,
@@ -236,7 +264,7 @@ test("card/detail share pending, accessible error/retry and confirmed-only succe
     );
     await waitFor(() => assert.equal(posts.length, 2));
     assert.equal(posts[0], posts[1]);
-    assert.equal(prepares, 1);
+    assert.equal(prepares, 2);
     assert.equal(runs.size, 1);
     await act(async () => {
       resolvePost();