diff --git a/server/src/plugins/tools.ts b/server/src/plugins/tools.ts
index 35aa4753..9036b0e3 100644
--- a/server/src/plugins/tools.ts
+++ b/server/src/plugins/tools.ts
@@ -85,8 +85,12 @@ export function grantedToolGuidance(tools: GrantedTool[]): string {
     ),
     "Use them for anything about those systems. Do NOT browse to one of their websites instead: your",
     "browser is signed in as nobody, so it sees less than these tools do and will meet a sign-in wall",
-    "that connecting an account has already solved. If one of these systems is involved but no tool",
-    "above covers the part you need, say which part is missing rather than going around it.",
+    "that connecting an account has already solved.",
+    "If one of these systems is involved and no tool above covers the part you need, that is a",
+    "missing grant and not something to work around. Say so plainly, name the capability you would",
+    "need, and say an administrator can grant it on that connector. Do not reach for the browser, do",
+    "not ask the person to sign in, and do not ask them to fetch it for you: they already have the",
+    "access, and the thing that is missing is yours, not theirs.",
   ].join("\n");
 }
 
diff --git a/server/tests/copilot.test.ts b/server/tests/copilot.test.ts
index ee623640..87791b21 100644
--- a/server/tests/copilot.test.ts
+++ b/server/tests/copilot.test.ts
@@ -537,6 +537,29 @@ describe("what a Bot is told it holds", () => {
     expect(grantedToolGuidance(drive).toLowerCase()).toContain("do not browse");
   });
 
+  test("says a gap in what it holds is a grant to ask for, not a wall to climb", () => {
+    /*
+     * The half of the Drive failure the "do not browse" line does not cover.
+     *
+     * Only `search_files` was granted. The Bot found the document, had no way to read it, and
+     * surfaced that as an authentication problem on `docs.google.com`: it opened the vendor, met
+     * Google's sign-in page and asked its person to take the wheel and sign in. They already had
+     * access. The Bot lacked a grant, and nothing on screen said so.
+     *
+     * A sentence naming the missing capability points at the screen that fixes it. A sign-in box
+     * does not, and asking the person to fetch it instead is the same mistake wearing a hat.
+     */
+    // Whitespace-normalised: the guidance is assembled line by line, so a sentence spans a newline
+    // wherever the source happened to wrap, which is not a fact about what the Bot is told.
+    const guidance = grantedToolGuidance(drive)
+      .toLowerCase()
+      .replace(/\s+/g, " ");
+    expect(guidance).toContain("missing grant");
+    expect(guidance).toContain("name the capability");
+    expect(guidance).toContain("administrator can grant it");
+    expect(guidance).toContain("do not ask the person to sign in");
+  });
+
   test("says nothing at all when the Bot holds nothing", () => {
     // A deployment with no connectors must not be told about connectors it does not have.
     expect(grantedToolGuidance([])).toBe("");