diff --git a/ui/src/pages/custodian/custodian-page.structured-wizard.test.ts b/ui/src/pages/custodian/custodian-page.structured-wizard.test.ts
index 2ffe6151dd09..b7ee6dc88120 100644
--- a/ui/src/pages/custodian/custodian-page.structured-wizard.test.ts
+++ b/ui/src/pages/custodian/custodian-page.structured-wizard.test.ts
@@ -19,7 +19,10 @@ describe("custodian structured wizard", () => {
     vi.restoreAllMocks();
   });
 
-  it("keeps a rejected typed answer active without showing a submitted receipt", async () => {
+  it.each([
+    { accepted: false, result: "rejected" },
+    { accepted: undefined, result: "ambiguous" },
+  ])("keeps a $result typed answer active as a plain user turn", async ({ accepted }) => {
     const step = {
       id: "port",
       type: "text" as const,
@@ -38,7 +41,7 @@ describe("custodian structured wizard", () => {
         sessionId: "validation-session",
         reply: "Enter port 18789.",
         action: "none",
-        wizardActionAccepted: false,
+        ...(accepted === undefined ? {} : { wizardActionAccepted: accepted }),
         wizardInputPending: true,
         step,
       });
@@ -63,7 +66,64 @@ describe("custodian structured wizard", () => {
     });
     expect(page.querySelector(".custodian__structured-response")).toBeNull();
     expect(page.querySelector(".custodian__wizard-step")).not.toBeNull();
-    expect(page.querySelector(".chat-group.user")).toBeNull();
+    expect(page.querySelector(".chat-group.user")?.textContent).toContain("banana");
+    const groups = [...page.querySelectorAll(".chat-group")];
+    const rejectedTurnIndex = groups.findIndex(
+      (group) => group.classList.contains("user") && group.textContent?.includes("banana"),
+    );
+    const guidanceIndex = groups.findIndex(
+      (group) =>
+        group.classList.contains("assistant") && group.textContent?.includes("Enter port 18789."),
+    );
+    expect(rejectedTurnIndex).toBeGreaterThanOrEqual(0);
+    expect(guidanceIndex).toBeGreaterThanOrEqual(0);
+    expect(rejectedTurnIndex).toBeLessThan(guidanceIndex);
+  });
+
+  it("keeps an ambiguously delivered sensitive answer masked as a plain user turn", async () => {
+    const step = {
+      id: "port",
+      type: "text" as const,
+      message: "Gateway port",
+      sensitive: true,
+    };
+    const request = vi
+      .fn()
+      .mockResolvedValueOnce({
+        sessionId: "uncertain-session",
+        reply: "Enter a port.",
+        action: "none",
+        sensitive: true,
+        wizardInputPending: true,
+        step,
+      })
+      .mockImplementationOnce(
+        async (_method: string, _params: unknown, options: { onSent?: () => void }) => {
+          options.onSent?.();
+          throw new Error("connection closed after send");
+        },
+      );
+    const { context } = createContext(request);
+    const { page } = await mountPage(context);
+
+    const input = await waitForFast(() => {
+      const element = page.querySelector<HTMLInputElement>(
+        '.custodian__wizard-step input[name="wizard-text"][type="password"]',
+      );
+      expect(element).not.toBeNull();
+      return element!;
+    });
+    input.value = "banana";
+    input.dispatchEvent(new Event("input", { bubbles: true }));
+    await page.updateComplete;
+    page.querySelector<HTMLButtonElement>(".custodian__wizard-step .btn.primary")!.click();
+
+    await waitForFast(() =>
+      expect(page.querySelector(".chat-group.user")?.textContent).toContain("Sensitive reply sent"),
+    );
+    expect(page.querySelector(".custodian__structured-response")).toBeNull();
+    expect(page.querySelector(".custodian__wizard-step")).not.toBeNull();
+    expect(page.innerHTML).not.toContain("banana");
   });
 
   it("does not confirm an answer after its Gateway client is replaced", async () => {
@@ -131,6 +191,7 @@ describe("custodian structured wizard", () => {
     await waitForFast(() => expect(page.textContent).toContain("Gateway connection changed"));
     expect(page.textContent).not.toContain("Answer submitted");
     expect(page.querySelector(".custodian__structured-response")).toBeNull();
+    expect(page.querySelector(".chat-group.user")?.textContent).toContain("18789");
   });
 
   it("keeps older-Gateway wizard answers as plain user turns", async () => {
diff --git a/ui/src/pages/custodian/custodian-session-store.ts b/ui/src/pages/custodian/custodian-session-store.ts
index 76d5c5384de4..01edfb10ddf9 100644
--- a/ui/src/pages/custodian/custodian-session-store.ts
+++ b/ui/src/pages/custodian/custodian-session-store.ts
@@ -244,7 +244,7 @@ export class CustodianSessionStore extends CustodianTranscriptState {
     params: SystemAgentChatParams,
     displayText: string,
     questionReply: boolean,
-    appendUserMessage = true,
+    userTurnProjection: "always" | "unless-accepted" = "always",
   ): Promise<eventNudgeState.CustodianSendOutcome> {
     const questionState = [this.answeredQuestions, this.questionReplyUncertain] as const;
     if (questionReply) {
@@ -252,25 +252,32 @@ export class CustodianSessionStore extends CustodianTranscriptState {
     }
     this.abandonedTurnOutcomeUnknown = false;
     this.answeredQuestions = retireCustodianQuestions(this.messages, this.answeredQuestions);
-    if (appendUserMessage) {
-      this.messages = [
-        ...this.messages,
-        {
-          id: this.nextMessageId++,
-          role: "user",
-          text: displayText,
-          at: Date.now(),
-          question: null,
-          step: null,
-          structuredResponse: null,
-        },
-      ];
+    const precedingMessage = this.messages.at(-1) ?? null;
+    const userMessage: CustodianMessage = {
+      id: this.nextMessageId++,
+      role: "user",
+      text: displayText,
+      at: Date.now(),
+      question: null,
+      step: null,
+      structuredResponse: null,
+    };
+    if (userTurnProjection === "always") {
+      this.messages = [...this.messages, userMessage];
     }
     this.input = "";
     this.emit();
     const reply = this.requestReply(client, params);
     const replyEpoch = this.requestEpoch;
     const outcome = await reply;
+    if (userTurnProjection === "unless-accepted" && outcome !== "accepted") {
+      // Owner-confirmed acceptance replaces the attempted turn with a receipt. Every other
+      // outcome keeps the masked display in its original transcript position.
+      const precedingIndex = precedingMessage ? this.messages.indexOf(precedingMessage) : -1;
+      if (precedingIndex >= 0) {
+        this.messages = this.messages.toSpliced(precedingIndex + 1, 0, userMessage);
+      }
+    }
     if (questionReply && this.requestEpoch === replyEpoch) {
       this.questionReplyUncertain = eventNudgeState.questionUncertainty(questionState[1], outcome);
       if (outcome === "rejected") {
diff --git a/ui/src/pages/custodian/custodian-structured-interaction.ts b/ui/src/pages/custodian/custodian-structured-interaction.ts
index 992afd7ab076..8ee871834068 100644
--- a/ui/src/pages/custodian/custodian-structured-interaction.ts
+++ b/ui/src/pages/custodian/custodian-structured-interaction.ts
@@ -25,7 +25,7 @@ type StructuredInteractionHost = {
     client: GatewayBrowserClient,
     params: SystemAgentChatParams,
     display: string,
-    appendUserMessage: boolean,
+    userTurnProjection: "always" | "unless-accepted",
   ) => Promise<eventNudgeState.CustodianSendOutcome>;
 };
 
@@ -76,7 +76,7 @@ export function createCustodianStructuredInteraction(host: StructuredInteraction
       params.client,
       params.request,
       params.display,
-      !state.wizardActionReceiptsAvailable,
+      state.wizardActionReceiptsAvailable ? "unless-accepted" : "always",
     );
     if (!state.wizardActionReceiptsAvailable) {
       return outcome;