diff --git a/extensions/discord/src/monitor/questions.test.ts b/extensions/discord/src/monitor/questions.test.ts
index c77e22ae0a52..e176b2f05c70 100644
--- a/extensions/discord/src/monitor/questions.test.ts
+++ b/extensions/discord/src/monitor/questions.test.ts
@@ -1,6 +1,15 @@
 // Discord question component feedback tests.
+import { InteractionResponseType, MessageFlags } from "discord-api-types/v10";
 import { describe, expect, it, vi } from "vitest";
-import type { ButtonInteraction } from "../internal/discord.js";
+import {
+  createInteraction as createDiscordInteraction,
+  type ButtonInteraction,
+} from "../internal/discord.js";
+import {
+  attachRestMock,
+  createInternalComponentInteractionPayload,
+  createInternalTestClient,
+} from "../internal/test-builders.test-support.js";
 import { createDiscordQuestionButton } from "./questions.js";
 
 type InteractionHarness = {
@@ -91,4 +100,99 @@ describe("Discord question button", () => {
       ephemeral: true,
     });
   });
+
+  it.each(
+    [
+      {
+        name: "submitted answer",
+        result: {
+          status: "answered" as const,
+          questionId: "target",
+          optionValue: "Production",
+        },
+        expectedText: "Answer submitted.",
+      },
+      {
+        name: "already answered question",
+        result: { status: "already-terminal" as const, reason: "already-terminal" as const },
+        expectedText: "This question was already answered.",
+      },
+      {
+        name: "question resolution failure",
+        error: new Error("question service unavailable"),
+        expectedText: "Could not submit this answer.",
+      },
+    ].flatMap((outcome) => [
+      { ...outcome, acknowledged: false },
+      { ...outcome, acknowledged: true },
+    ]),
+  )("delivers $name feedback when acknowledgement is $acknowledged", async (testCase) => {
+    const client = createInternalTestClient();
+    const post = vi.fn(async () => undefined);
+    if (!testCase.acknowledged) {
+      post.mockRejectedValueOnce(new Error("temporary connection reset"));
+    }
+    attachRestMock(client, { post });
+    const interaction = createDiscordInteraction(
+      client,
+      createInternalComponentInteractionPayload({
+        id: "interaction-1",
+        token: "interaction-token",
+        user: {
+          id: "user-1",
+          username: "Alice",
+          discriminator: "0",
+          avatar: null,
+          global_name: null,
+        },
+      }),
+    ) as ButtonInteraction;
+    const resolveQuestion = vi.fn(async () => {
+      if (testCase.error) {
+        throw testCase.error;
+      }
+      return testCase.result;
+    });
+    const button = createDiscordQuestionButton({
+      cfg: {} as never,
+      accountId: "default",
+      authorizeQuestion: vi.fn(async () => true),
+      resolveQuestion: resolveQuestion as never,
+    });
+
+    await button.run(interaction, {
+      id: "ask_0123456789abcdef0123456789abcdef",
+      i: "1",
+    });
+
+    expect(resolveQuestion).toHaveBeenCalledOnce();
+    expect(post).toHaveBeenNthCalledWith(
+      1,
+      "/interactions/interaction-1/interaction-token/callback",
+      {
+        body: { type: InteractionResponseType.DeferredMessageUpdate },
+      },
+    );
+    if (testCase.acknowledged) {
+      expect(post).toHaveBeenNthCalledWith(
+        2,
+        "/webhooks/app1/interaction-token",
+        { body: { content: testCase.expectedText, flags: MessageFlags.Ephemeral } },
+        undefined,
+      );
+      expect(interaction.responseState).toBe("deferred-update");
+    } else {
+      expect(post).toHaveBeenNthCalledWith(
+        2,
+        "/interactions/interaction-1/interaction-token/callback",
+        {
+          body: {
+            type: InteractionResponseType.ChannelMessageWithSource,
+            data: { content: testCase.expectedText, flags: MessageFlags.Ephemeral },
+          },
+        },
+      );
+      expect(interaction.responseState).toBe("replied");
+    }
+  });
 });
diff --git a/extensions/discord/src/monitor/questions.ts b/extensions/discord/src/monitor/questions.ts
index c6abedebe4ed..90636ee31ea0 100644
--- a/extensions/discord/src/monitor/questions.ts
+++ b/extensions/discord/src/monitor/questions.ts
@@ -41,31 +41,28 @@ class QuestionButton extends Button {
     try {
       await interaction.acknowledge();
     } catch {}
-    let result: Awaited<ReturnType<QuestionResolver>>;
+    let content: string;
     try {
-      result = await this.ctx.resolveQuestion({
+      const result = await this.ctx.resolveQuestion({
         cfg: this.ctx.cfg,
         questionId: callback.questionId,
         optionIndex: callback.optionIndex,
         senderId: interaction.userId,
         clientDisplayName: `Discord question (${this.ctx.accountId})`,
       });
+      content =
+        result.status === "answered" ? "Answer submitted." : "This question was already answered.";
     } catch {
-      try {
-        await interaction.followUp({ content: "Could not submit this answer.", ephemeral: true });
-      } catch {}
-      return;
+      content = "Could not submit this answer.";
     }
     try {
-      await interaction.followUp({
-        content:
-          result.status === "answered"
-            ? "Answer submitted."
-            : "This question was already answered.",
-        ephemeral: true,
-      });
+      const feedback = { content, ephemeral: true };
+      // A rejected acknowledgement leaves the initial callback available, not the webhook.
+      await (interaction.responseState === "unacknowledged"
+        ? interaction.reply(feedback)
+        : interaction.followUp(feedback));
     } catch {
-      // Gateway state already committed; receipt delivery is best-effort.
+      // Gateway state may already be committed; receipt delivery is best-effort.
     }
   }
 }