diff --git a/src/hooks/.sisyphus/ralph-loop.local.md b/src/hooks/.sisyphus/ralph-loop.local.md
new file mode 100644
index 000000000..fd670d82b
--- /dev/null
+++ b/src/hooks/.sisyphus/ralph-loop.local.md
@@ -0,0 +1,12 @@
+---
+active: true
+iteration: 2
+max_iterations: 100
+completion_promise: "DONE"
+initial_completion_promise: "DONE"
+started_at: "2026-03-14T04:20:58.486Z"
+session_id: "new-session-1"
+strategy: "reset"
+message_count_at_start: 0
+---
+Build feature
diff --git a/src/hooks/keyword-detector/hook.ts b/src/hooks/keyword-detector/hook.ts
index ea6348419..2a1462970 100644
--- a/src/hooks/keyword-detector/hook.ts
+++ b/src/hooks/keyword-detector/hook.ts
@@ -17,13 +17,18 @@ 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
 
 function extractUltraworkTask(cleanText: string): string {
+  if (TRAILING_GREETING_ULTRAWORK_PATTERN.test(cleanText)) {
+    return ""
+  }
+
   return cleanText.replace(ULTRAWORK_KEYWORD_PATTERN, "").trim()
 }
 
-function hasLeadingUltraworkKeyword(cleanText: string): boolean {
-  return LEADING_ULTRAWORK_PATTERN.test(cleanText)
+function hasEdgeUltraworkKeyword(cleanText: string): boolean {
+  return LEADING_ULTRAWORK_PATTERN.test(cleanText) || TRAILING_GREETING_ULTRAWORK_PATTERN.test(cleanText)
 }
 
 export function createKeywordDetectorHook(
@@ -81,11 +86,11 @@ export function createKeywordDetectorHook(
         }
       }
 
-      if (!hasLeadingUltraworkKeyword(cleanText)) {
+      if (!hasEdgeUltraworkKeyword(cleanText)) {
         const preFilterCount = detectedKeywords.length
         detectedKeywords = detectedKeywords.filter((k) => k.type !== "ultrawork")
         if (preFilterCount > detectedKeywords.length) {
-          log(`[keyword-detector] Filtered non-leading ultrawork keyword`, {
+          log(`[keyword-detector] Filtered non-edge ultrawork keyword`, {
             sessionID: input.sessionID,
           })
         }
diff --git a/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts b/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts
new file mode 100644
index 000000000..2ec21dec3
--- /dev/null
+++ b/src/hooks/keyword-detector/ultrawork-edge-trigger.test.ts
@@ -0,0 +1,122 @@
+import { afterEach, beforeEach, describe, expect, test } from "bun:test"
+
+import { createKeywordDetectorHook } from "./index"
+import { _resetForTesting, setMainSession } from "../../features/claude-code-session-state"
+
+type StartLoopCall = {
+  sessionID: string
+  prompt: string
+  options: Record<string, unknown>
+}
+
+function createMockPluginInput(toastCalls: string[] = []) {
+  return {
+    client: {
+      tui: {
+        showToast: async (opts: { body: { title: string } }) => {
+          toastCalls.push(opts.body.title)
+        },
+      },
+    },
+  } as any
+}
+
+function createMockRalphLoop(startLoopCalls: StartLoopCall[]) {
+  return {
+    startLoop: (sessionID: string, prompt: string, options?: Record<string, unknown>): boolean => {
+      startLoopCalls.push({ sessionID, prompt, options: options ?? {} })
+      return true
+    },
+  }
+}
+
+describe("keyword-detector ultrawork edge trigger", () => {
+  beforeEach(() => {
+    _resetForTesting()
+    setMainSession("main-session")
+  })
+
+  afterEach(() => {
+    _resetForTesting()
+  })
+
+  test("#given greeting text before ulw and surrounding whitespace #when chat.message fires #then ultrawork still activates", 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: " hi there ulw " }],
+    }
+
+    // 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: "Complete the task as instructed",
+      options: {
+        ultrawork: true,
+        maxIterations: undefined,
+        completionPromise: undefined,
+        strategy: undefined,
+      },
+    })
+    expect(output.parts[0]?.text).toContain("ULTRAWORK MODE ENABLED!")
+    expect(output.parts[0]?.text).toContain(" hi there ulw ")
+  })
+
+  test("#given ulw mentioned in the middle of a sentence #when chat.message fires #then ultrawork stays disabled", 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: "I think ulw is cool" }],
+    }
+
+    // when
+    await hook["chat.message"]({ sessionID: "main-session", agent: "sisyphus" }, output)
+
+    // then
+    expect(toastCalls).not.toContain("Ultrawork Mode Activated")
+    expect(startLoopCalls).toHaveLength(0)
+    expect(output.parts[0]?.text).toBe("I think ulw is cool")
+  })
+
+  test("#given trailing ultrawork reference without punctuation #when chat.message fires #then ultrawork stays disabled", 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: "what is ultrawork" }],
+    }
+
+    // when
+    await hook["chat.message"]({ sessionID: "main-session", agent: "sisyphus" }, output)
+
+    // then
+    expect(toastCalls).not.toContain("Ultrawork Mode Activated")
+    expect(startLoopCalls).toHaveLength(0)
+    expect(output.parts[0]?.text).toBe("what is ultrawork")
+  })
+})