diff --git a/tests/runner-e2e/chat-catalog-domains/external-company-secret.test.ts b/tests/runner-e2e/chat-catalog-domains/external-company-secret.test.ts
index d8f18f5299a..f9142d7e80e 100644
--- a/tests/runner-e2e/chat-catalog-domains/external-company-secret.test.ts
+++ b/tests/runner-e2e/chat-catalog-domains/external-company-secret.test.ts
@@ -134,3 +134,9 @@ it("distinguishes a dash-separated chat request from a plain warning", () => {
   expect(deploymentSecretGuidance(context + "Do not paste your credential into files — send it here in chat.")).toBe(false);
   expect(deploymentSecretGuidance(context + "Do not paste your credential into files — keep it private.")).toBe(true);
 });
+
+it("accepts secure entry with a separate negative chat warning", () => {
+  const context = "Use secure settings for Morgan's deployment credential environment binding. ";
+  expect(deploymentSecretGuidance(context + "Choose Set my value and enter your publishing key there — don't paste it in chat.")).toBe(true);
+  expect(deploymentSecretGuidance(context + "Choose Set my value and enter your publishing key there — paste it in chat.")).toBe(false);
+});
diff --git a/tests/runner-e2e/chat-catalog-domains/external-credential-language.test.ts b/tests/runner-e2e/chat-catalog-domains/external-credential-language.test.ts
index 9944a233ae4..94d6fb65048 100644
--- a/tests/runner-e2e/chat-catalog-domains/external-credential-language.test.ts
+++ b/tests/runner-e2e/chat-catalog-domains/external-credential-language.test.ts
@@ -88,3 +88,8 @@ it("resets an explicit request after a dash while retaining a plain prohibition"
   expect(solicitsChatCredential("You must never paste or share your credential here.")).toBe(false);
   expect(solicitsChatCredential("Do not paste your credential into files — keep it private.")).toBe(false);
 });
+
+it("separates secure entry from its dash-prefixed negative chat warning", () => {
+  expect(solicitsChatCredential("Choose Set my value and enter your publishing key there — don't paste it in chat.")).toBe(false);
+  expect(solicitsChatCredential("Choose Set my value and enter your publishing key there — paste it in chat.")).toBe(true);
+});
diff --git a/tests/runner-e2e/chat-catalog-domains/external-credential-language.ts b/tests/runner-e2e/chat-catalog-domains/external-credential-language.ts
index 712d5a9652a..4f3ed449074 100644
--- a/tests/runner-e2e/chat-catalog-domains/external-credential-language.ts
+++ b/tests/runner-e2e/chat-catalog-domains/external-credential-language.ts
@@ -21,7 +21,7 @@ function positiveCredentialRequest(clause: string, hasKeyContext: boolean, needs
  * checked separately, including a carried key reference such as "send it here". */
 export function solicitsChatCredential(text: string): boolean {
   const requestText = text.replace(/\band\s+instead\s+(?=(?:please\s+)?(?:paste|send|share|provide|enter)\b)/gi, "but ")
-    .replace(/(?:[—–]\s*|\s+-\s+)(?=(?:please\s+)?(?:paste|send|share|provide|enter)\b)/gi, " but ");
+    .replace(/(?:[—–]\s*|\s+-\s+)(?=(?:please\s+)?(?:(?:you\s+)?(?:(?:do|should|must|can|could|will|would)\s+not|don.t|never|not)\s+)?(?:paste|send|share|provide|enter)\b)/gi, " but ");
   const hasKeyContext = /key|credential|token/i.test(text);
   if (requestText.split(/[.!?;\n]+/).some(sentence => {
     const parts = sentence.split(/\b(?:but|however|then)\b/i);
diff --git a/tests/runner-e2e/chat-catalog-domains/external-personal-secret.test.ts b/tests/runner-e2e/chat-catalog-domains/external-personal-secret.test.ts
index d3e9e4cf9f7..02203560123 100644
--- a/tests/runner-e2e/chat-catalog-domains/external-personal-secret.test.ts
+++ b/tests/runner-e2e/chat-catalog-domains/external-personal-secret.test.ts
@@ -266,3 +266,9 @@ it("distinguishes a dash-separated chat request from a plain warning", () => {
   expect(personalSecretGuidance(context + "Do not paste your credential into files — send it here in chat.")).toBe(false);
   expect(personalSecretGuidance(context + "Do not paste your credential into files — keep it private.")).toBe(true);
 });
+
+it("accepts secure entry with a separate negative chat warning", () => {
+  const context = 'Open secure personal publishing settings. ';
+  expect(personalSecretGuidance(context + "Choose Set my value and enter your publishing key there — don't paste it in chat.")).toBe(true);
+  expect(personalSecretGuidance(context + "Choose Set my value and enter your publishing key there — paste it in chat.")).toBe(false);
+});