diff --git a/src/shared/internal-initiator-marker.test.ts b/src/shared/internal-initiator-marker.test.ts
new file mode 100644
index 000000000..cc1035dd8
--- /dev/null
+++ b/src/shared/internal-initiator-marker.test.ts
@@ -0,0 +1,119 @@
+import { describe, expect, test } from "bun:test"
+import {
+  OMO_INTERNAL_INITIATOR_MARKER,
+  createInternalAgentTextPart,
+  stripInternalInitiatorMarkers,
+} from "./internal-initiator-marker"
+
+describe("internal-initiator-marker", () => {
+  describe("createInternalAgentTextPart", () => {
+    test("#given clean text #when creating an internal agent text part #then appends exactly one marker", () => {
+      // given
+      const text = "Hello world"
+
+      // when
+      const part = createInternalAgentTextPart(text)
+
+      // then
+      expect(part.type).toBe("text")
+      expect(part.text).toBe(`Hello world\n${OMO_INTERNAL_INITIATOR_MARKER}`)
+    })
+
+    test("#given text already ending with the marker #when creating a text part #then does not duplicate the marker", () => {
+      // given
+      const text = `Already marked\n${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const part = createInternalAgentTextPart(text)
+
+      // then
+      const markerCount = part.text.split(OMO_INTERNAL_INITIATOR_MARKER).length - 1
+      expect(markerCount).toBe(1)
+      expect(part.text).toBe(`Already marked\n${OMO_INTERNAL_INITIATOR_MARKER}`)
+    })
+
+    test("#given text containing multiple embedded markers #when creating a text part #then collapses to a single trailing marker", () => {
+      // given
+      const text = `First\n${OMO_INTERNAL_INITIATOR_MARKER}\nSecond\n${OMO_INTERNAL_INITIATOR_MARKER}\nThird\n${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const part = createInternalAgentTextPart(text)
+
+      // then
+      const markerCount = part.text.split(OMO_INTERNAL_INITIATOR_MARKER).length - 1
+      expect(markerCount).toBe(1)
+      expect(part.text.endsWith(OMO_INTERNAL_INITIATOR_MARKER)).toBe(true)
+    })
+
+    test("#given text with embedded markers between content #when creating a text part #then strips embedded markers and keeps content", () => {
+      // given
+      const text = `Line one\n${OMO_INTERNAL_INITIATOR_MARKER}\nLine two\n${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const part = createInternalAgentTextPart(text)
+
+      // then
+      expect(part.text).toContain("Line one")
+      expect(part.text).toContain("Line two")
+      const markerCount = part.text.split(OMO_INTERNAL_INITIATOR_MARKER).length - 1
+      expect(markerCount).toBe(1)
+    })
+
+    test("#given empty text #when creating a text part #then still appends a single marker", () => {
+      // given
+      const text = ""
+
+      // when
+      const part = createInternalAgentTextPart(text)
+
+      // then
+      expect(part.text).toBe(`\n${OMO_INTERNAL_INITIATOR_MARKER}`)
+    })
+  })
+
+  describe("stripInternalInitiatorMarkers", () => {
+    test("#given text with no markers #when stripping #then returns text trimmed at the end", () => {
+      // given
+      const text = "No markers here"
+
+      // when
+      const result = stripInternalInitiatorMarkers(text)
+
+      // then
+      expect(result).toBe("No markers here")
+    })
+
+    test("#given text with one trailing marker #when stripping #then removes the marker", () => {
+      // given
+      const text = `Content\n${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const result = stripInternalInitiatorMarkers(text)
+
+      // then
+      expect(result).toBe("Content")
+    })
+
+    test("#given text with multiple stacked markers #when stripping #then removes all of them", () => {
+      // given
+      const text = `Content\n${OMO_INTERNAL_INITIATOR_MARKER}\n${OMO_INTERNAL_INITIATOR_MARKER}\n${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const result = stripInternalInitiatorMarkers(text)
+
+      // then
+      expect(result).toBe("Content")
+    })
+
+    test("#given text with markers on consecutive lines without separators #when stripping #then removes all markers", () => {
+      // given
+      const text = `${OMO_INTERNAL_INITIATOR_MARKER}${OMO_INTERNAL_INITIATOR_MARKER}${OMO_INTERNAL_INITIATOR_MARKER}`
+
+      // when
+      const result = stripInternalInitiatorMarkers(text)
+
+      // then
+      expect(result).toBe("")
+    })
+  })
+})
diff --git a/src/shared/internal-initiator-marker.ts b/src/shared/internal-initiator-marker.ts
index 3e19c5819..7e810a15e 100644
--- a/src/shared/internal-initiator-marker.ts
+++ b/src/shared/internal-initiator-marker.ts
@@ -1,11 +1,18 @@
 export const OMO_INTERNAL_INITIATOR_MARKER = "<!-- OMO_INTERNAL_INITIATOR -->"
 
+const INTERNAL_INITIATOR_MARKER_PATTERN = /\n*<!--\s*OMO_INTERNAL_INITIATOR\s*-->\s*/g
+
+export function stripInternalInitiatorMarkers(text: string): string {
+  return text.replace(INTERNAL_INITIATOR_MARKER_PATTERN, "").trimEnd()
+}
+
 export function createInternalAgentTextPart(text: string): {
   type: "text"
   text: string
 } {
+  const cleanText = stripInternalInitiatorMarkers(text)
   return {
     type: "text",
-    text: `${text}\n${OMO_INTERNAL_INITIATOR_MARKER}`,
+    text: `${cleanText}\n${OMO_INTERNAL_INITIATOR_MARKER}`,
   }
 }
diff --git a/src/shared/system-directive.test.ts b/src/shared/system-directive.test.ts
index 9da4c9563..2626bb771 100644
--- a/src/shared/system-directive.test.ts
+++ b/src/shared/system-directive.test.ts
@@ -144,6 +144,50 @@ const x = 1;
       const directive = `  ${createSystemDirective("TEST")}`
       expect(isSystemDirective(directive)).toBe(true)
     })
+
+    test("#given a ralph-loop ULW continuation prefixed with 'ultrawork ' #when checking system directive #then returns true", () => {
+      // given
+      const directive = `ultrawork ${createSystemDirective("RALPH LOOP 2/500")}\n\nYour previous attempt did not output the completion promise.`
+
+      // when
+      const result = isSystemDirective(directive)
+
+      // then
+      expect(result).toBe(true)
+    })
+
+    test("#given a continuation prefixed with 'ulw ' shorthand #when checking system directive #then returns true", () => {
+      // given
+      const directive = `ulw ${createSystemDirective("ULTRAWORK LOOP VERIFICATION 1/500")}\n\nYou already emitted <promise>DONE</promise>.`
+
+      // when
+      const result = isSystemDirective(directive)
+
+      // then
+      expect(result).toBe(true)
+    })
+
+    test("#given a continuation prefixed with uppercase 'ULTRAWORK ' #when checking system directive #then returns true", () => {
+      // given
+      const directive = `ULTRAWORK ${createSystemDirective("RALPH LOOP 5/500")}`
+
+      // when
+      const result = isSystemDirective(directive)
+
+      // then
+      expect(result).toBe(true)
+    })
+
+    test("#given user text that legitimately starts with 'ultrawork' word #when no directive follows #then returns false", () => {
+      // given
+      const text = "ultrawork is a great mode but I have a question about it"
+
+      // when
+      const result = isSystemDirective(text)
+
+      // then
+      expect(result).toBe(false)
+    })
   })
 
   describe("integration with keyword detection", () => {
diff --git a/src/shared/system-directive.ts b/src/shared/system-directive.ts
index f2ae8c602..001017aa5 100644
--- a/src/shared/system-directive.ts
+++ b/src/shared/system-directive.ts
@@ -7,6 +7,8 @@
 
 export const SYSTEM_DIRECTIVE_PREFIX = "[SYSTEM DIRECTIVE: OH-MY-OPENCODE"
 
+const SYSTEM_DIRECTIVE_LEADING_KEYWORD_PATTERN = /^\s*(?:ultrawork|ulw)\s+/i
+
 /**
  * Creates a system directive header with the given type.
  * @param type - The directive type (e.g., "TODO CONTINUATION", "RALPH LOOP")
@@ -23,7 +25,12 @@ export function createSystemDirective(type: string): string {
  * @returns true if the message is a system directive
  */
 export function isSystemDirective(text: string): boolean {
-  return text.trimStart().startsWith(SYSTEM_DIRECTIVE_PREFIX)
+  const trimmed = text.trimStart()
+  if (trimmed.startsWith(SYSTEM_DIRECTIVE_PREFIX)) {
+    return true
+  }
+  const withoutLeadingKeyword = trimmed.replace(SYSTEM_DIRECTIVE_LEADING_KEYWORD_PATTERN, "")
+  return withoutLeadingKeyword.startsWith(SYSTEM_DIRECTIVE_PREFIX)
 }
 
 /**