diff --git a/studio/backend/core/inference/llama_cpp.py b/studio/backend/core/inference/llama_cpp.py
index 1207395ed6..2650168efd 100644
--- a/studio/backend/core/inference/llama_cpp.py
+++ b/studio/backend/core/inference/llama_cpp.py
@@ -69,10 +69,11 @@ _INTENT_SIGNAL = re.compile(
     r"here (?:is|are) (?:my |the |a )?(?:plan|approach|steps))"
     r"|"
     # Bare "Plan:" / "Approach:" (optionally preceded by a determiner
-    # like "My" / "The" / "Our") anchored to start of line so direct
-    # answers like "Here is a lesson plan:" or "meal plan:" do not trip
-    # the re-prompt path.
-    r"(?:^|\r?\n)[ \t]*(?:(?:my|the|our|a|this|that)\s+)?(?:plan|approach):"
+    # like "My" / "The" / "Our") anchored to start of line AND followed
+    # by a newline. Inline forms like "Your current Plan: Pro includes
+    # local chats" or "The plan: $10/month" must NOT trip the re-prompt
+    # path; only header-style framings ("Plan:\n1. ...") count.
+    r"(?:^|\r?\n)[ \t]*(?:(?:my|the|our|a|this|that)\s+)?(?:plan|approach):[ \t]*(?=\r?\n)"
     r"|"
     # "Now I" / "Next I" patterns
     r"\b(?:now i|next i)\b"
@@ -138,7 +139,7 @@ _PLAN_LIST_FRAMING = re.compile(
     r"\b(?:search|look up|call|use|fetch|browse|run|execute|"
     r"check|find|open|verify|compare|summari[sz]e|think|respond|"
     r"answer|analy[sz]e|explore|outline|gather|query|reason)\b"
-    r"|(?:^|\r?\n)[ \t]*(?:(?:my|the|our|a|this|that)\s+)?(?:plan|approach):",
+    r"|(?:^|\r?\n)[ \t]*(?:(?:my|the|our|a|this|that)\s+)?(?:plan|approach):[ \t]*(?=\r?\n)",
     re.IGNORECASE,
 )
 
diff --git a/studio/backend/tests/test_llama_cpp_reprompt_guard.py b/studio/backend/tests/test_llama_cpp_reprompt_guard.py
index 955dc423eb..8923a8294c 100644
--- a/studio/backend/tests/test_llama_cpp_reprompt_guard.py
+++ b/studio/backend/tests/test_llama_cpp_reprompt_guard.py
@@ -335,13 +335,14 @@ def test_reprompts_on_incomplete_html_intent():
 
 
 def test_reprompts_on_plan_colon_intent():
-    """Bare ``Plan:`` / ``Approach:`` at the start of a structured reply
-    is now an intent signal so the plan stall re-prompts. Pre-fix the
-    response slipped past ``_INTENT_SIGNAL`` entirely."""
+    """Bare ``Plan:`` / ``Approach:`` followed by a newline at the start
+    of a structured reply is now an intent signal so the plan stall
+    re-prompts. Inline ``Plan: <text>`` (no newline) is NOT an intent
+    signal because that shape is common in marketing / product answers
+    such as ``Plan: Pro is $10/month``."""
     samples = [
         "Plan:\n1. search the docs\n2. summarise",
         "Approach:\n1. fetch the data\n2. compare",
-        "Plan: search the docs then summarise",
     ]
     for s in samples:
         assert _INTENT_SIGNAL.search(s), s
@@ -403,17 +404,25 @@ def test_plan_colon_intent_is_line_anchored():
     re-prompt path and risk wiping a valid response."""
     # These mid-line "plan:" / "approach:" mentions are NOT intent signals.
     # The qualifier before "plan" is a content noun ("lesson", "meal",
-    # "migration") rather than a generic determiner ("my", "the", ...).
+    # "migration") rather than a generic determiner, OR the colon is
+    # followed by inline content instead of a newline-anchored header.
     direct_answers = [
         "Here is a lesson plan:\n1. Warm-up\n2. Group practice\n3. Assessment",
         "I prepared a meal plan: rice, beans, eggs.",
         "Quick approach: top-down then bottom-up.",
+        "Your current Plan: Pro includes local chats.",
+        "The plan: Basic is free, Pro is $10/month, Enterprise is custom.",
+        "My plan: use dynamic programming with memoisation.",
+        "Recommended approach: use the Python SDK for uploads.",
+        "The migration plan: backup, run, verify all in one window.",
     ]
     for s in direct_answers:
         assert not _INTENT_SIGNAL.search(s), s
         assert not _would_reprompt(s), s
     # "Plan:" / "Approach:" with optional generic determiner at the start
-    # of a line IS an intent signal.
+    # of a line, FOLLOWED BY A NEWLINE, IS an intent signal. The newline
+    # requirement is what filters inline product/answer text such as
+    # "The plan: Pro is $10/month" out of the intent path.
     plan_starts = [
         "Plan:\n1. search\n2. summarise",
         "Approach:\n1. fetch\n2. compare",