diff --git a/src/auto-reply/tokens.test.ts b/src/auto-reply/tokens.test.ts
new file mode 100644
index 000000000..c8cee251a
--- /dev/null
+++ b/src/auto-reply/tokens.test.ts
@@ -0,0 +1,37 @@
+import { describe, it, expect } from "vitest";
+import { isSilentReplyText } from "./tokens.js";
+
+describe("isSilentReplyText", () => {
+  it("returns true for exact token", () => {
+    expect(isSilentReplyText("NO_REPLY")).toBe(true);
+  });
+
+  it("returns true for token with surrounding whitespace", () => {
+    expect(isSilentReplyText("  NO_REPLY  ")).toBe(true);
+    expect(isSilentReplyText("\nNO_REPLY\n")).toBe(true);
+  });
+
+  it("returns false for undefined/empty", () => {
+    expect(isSilentReplyText(undefined)).toBe(false);
+    expect(isSilentReplyText("")).toBe(false);
+  });
+
+  it("returns false for substantive text ending with token (#19537)", () => {
+    const text = "Here is a helpful response.\n\nNO_REPLY";
+    expect(isSilentReplyText(text)).toBe(false);
+  });
+
+  it("returns false for substantive text starting with token", () => {
+    const text = "NO_REPLY but here is more content";
+    expect(isSilentReplyText(text)).toBe(false);
+  });
+
+  it("returns false for token embedded in text", () => {
+    expect(isSilentReplyText("Please NO_REPLY to this")).toBe(false);
+  });
+
+  it("works with custom token", () => {
+    expect(isSilentReplyText("HEARTBEAT_OK", "HEARTBEAT_OK")).toBe(true);
+    expect(isSilentReplyText("Checked inbox. HEARTBEAT_OK", "HEARTBEAT_OK")).toBe(false);
+  });
+});
diff --git a/src/auto-reply/tokens.ts b/src/auto-reply/tokens.ts
index c0bce2a2d..18cabceaa 100644
--- a/src/auto-reply/tokens.ts
+++ b/src/auto-reply/tokens.ts
@@ -11,12 +11,10 @@ export function isSilentReplyText(
     return false;
   }
   const escaped = escapeRegExp(token);
-  const prefix = new RegExp(`^\\s*${escaped}(?=$|\\W)`);
-  if (prefix.test(text)) {
-    return true;
-  }
-  const suffix = new RegExp(`\\b${escaped}\\b\\W*$`);
-  return suffix.test(text);
+  // Only match when the entire response (trimmed) is the silent token,
+  // optionally surrounded by whitespace/punctuation. This prevents
+  // substantive replies ending with NO_REPLY from being suppressed (#19537).
+  return new RegExp(`^\\s*${escaped}\\s*$`).test(text);
 }
 
 export function isSilentReplyPrefixText(