diff --git a/src/hooks/keyword-detector/hook.ts b/src/hooks/keyword-detector/hook.ts
index 2a1462970..52a5a292b 100644
--- a/src/hooks/keyword-detector/hook.ts
+++ b/src/hooks/keyword-detector/hook.ts
@@ -17,18 +17,20 @@ import { parseRalphLoopArguments } from "../ralph-loop/command-arguments"
 
 const ULTRAWORK_KEYWORD_PATTERN = /\b(ultrawork|ulw)\b/i
 const LEADING_ULTRAWORK_PATTERN = /^\s*(ultrawork|ulw)\b/i
-const TRAILING_GREETING_ULTRAWORK_PATTERN = /^\s*(?:hi|hello|hey|hiya|greetings)(?:\s+there)?\s+(ultrawork|ulw)\s*$/i
+const GREETING_PREFIX_ULTRAWORK_PATTERN = /^\s*(?:hi|hello|hey|hiya|greetings)(?:\s+there)?(?:[!,.:;-]+\s*|\s+)(ultrawork|ulw)\b/i
 
 function extractUltraworkTask(cleanText: string): string {
-  if (TRAILING_GREETING_ULTRAWORK_PATTERN.test(cleanText)) {
-    return ""
+  const greetingPrefixedMatch = cleanText.match(GREETING_PREFIX_ULTRAWORK_PATTERN)
+
+  if (greetingPrefixedMatch) {
+    return cleanText.slice(greetingPrefixedMatch[0].length).trim()
   }
 
   return cleanText.replace(ULTRAWORK_KEYWORD_PATTERN, "").trim()
 }
 
 function hasEdgeUltraworkKeyword(cleanText: string): boolean {
-  return LEADING_ULTRAWORK_PATTERN.test(cleanText) || TRAILING_GREETING_ULTRAWORK_PATTERN.test(cleanText)
+  return LEADING_ULTRAWORK_PATTERN.test(cleanText) || GREETING_PREFIX_ULTRAWORK_PATTERN.test(cleanText)
 }
 
 export function createKeywordDetectorHook(
diff --git a/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts b/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts
index 2ec21dec3..0fc7e8f30 100644
--- a/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts
+++ b/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts
@@ -74,6 +74,40 @@ describe("keyword-detector ultrawork edge trigger", () => {
     expect(output.parts[0]?.text).toContain(" hi there ulw ")
   })
 
+  test("#given greeting before ulw with a trailing task #when chat.message fires #then ultrawork activates and preserves the task", async () => {
+    // given
+    const toastCalls: string[] = []
+    const startLoopCalls: StartLoopCall[] = []
+    const hook = createKeywordDetectorHook(
+      createMockPluginInput(toastCalls),
+      undefined,
+      createMockRalphLoop(startLoopCalls),
+    )
+    const output = {
+      message: {} as Record<string, unknown>,
+      parts: [{ type: "text", text: "hey ulw fix the flaky keyword tests" }],
+    }
+
+    // when
+    await hook["chat.message"]({ sessionID: "main-session", agent: "sisyphus" }, output)
+
+    // then
+    expect(toastCalls).toContain("Ultrawork Mode Activated")
+    expect(startLoopCalls).toHaveLength(1)
+    expect(startLoopCalls[0]).toEqual({
+      sessionID: "main-session",
+      prompt: "fix the flaky keyword tests",
+      options: {
+        ultrawork: true,
+        maxIterations: undefined,
+        completionPromise: undefined,
+        strategy: undefined,
+      },
+    })
+    expect(output.parts[0]?.text).toContain("ULTRAWORK MODE ENABLED!")
+    expect(output.parts[0]?.text).toContain("hey ulw fix the flaky keyword tests")
+  })
+
   test("#given ulw mentioned in the middle of a sentence #when chat.message fires #then ultrawork stays disabled", async () => {
     // given
     const toastCalls: string[] = []