diff --git a/ARCHITECTURE.md b/ARCHITECTURE.md
index c9834c36..55884d71 100644
--- a/ARCHITECTURE.md
+++ b/ARCHITECTURE.md
@@ -123,7 +123,7 @@ Environment variables controlling behavior:
     HERMES_WEBUI_PASSWORD          Optional: enable password auth (off by default)
     HERMES_WEBUI_SKIP_ONBOARDING   Optional: bypass the first-run onboarding wizard
     HERMES_PREFILL_MESSAGES_FILE   Optional JSON message list for browser-turn prefill context
-    HERMES_WEBUI_PREFILL_MESSAGES_SCRIPT Optional command that prints JSON messages or text prefill context
+    HERMES_WEBUI_PREFILL_MESSAGES_SCRIPT Optional command that prints JSON messages or plain-text user prefill context
     HERMES_WEBUI_PREFILL_MESSAGES_SCRIPT_TIMEOUT Optional script timeout in seconds (default 5, max 30)
     HERMES_HOME                    Base directory for Hermes state (~/.hermes by default)
 
diff --git a/CHANGELOG.md b/CHANGELOG.md
index c365129f..dc1737b4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Plain-text `webui_prefill_messages_script` output is now wrapped as a `user` prefill message instead of an extra `system` message, keeping dynamic recall context provider-safe while preserving explicit JSON message roles.
+
 ## [v0.51.145] — 2026-05-26 — Release DQ (stage-batch27 — sidebar running-state preservation)
 
 ### Fixed
diff --git a/README.md b/README.md
index 7120dfa7..903c4b6d 100644
--- a/README.md
+++ b/README.md
@@ -154,10 +154,11 @@ HERMES_WEBUI_PREFILL_MESSAGES_SCRIPT_TIMEOUT=5 \
 ```
 
 The script may print either an OpenAI-style JSON message list, a JSON object with
-a `messages` list, or plain text; plain text is wrapped as one `system` prefill
-message. Script output is capped at 256 KiB before parsing. The browser only
-receives a compact status event (`source`, `label`, message count, and redacted
-errors), never the prefill message bodies.
+a `messages` list, or plain text; plain text is wrapped as one `user` prefill
+message so dynamic recall text becomes ordinary context instead of an extra
+system instruction. Script output is capped at 256 KiB before parsing. The
+browser only receives a compact status event (`source`, `label`, message count,
+and redacted errors), never the prefill message bodies.
 
 The bootstrap will:
 
diff --git a/api/streaming.py b/api/streaming.py
index a77a442c..bd640ae9 100644
--- a/api/streaming.py
+++ b/api/streaming.py
@@ -340,7 +340,7 @@ def _messages_from_prefill_script_output(text: str) -> list[dict]:
     messages = _valid_prefill_messages(payload)
     if messages:
         return messages
-    return [{"role": "system", "content": stripped}]
+    return [{"role": "user", "content": stripped}]
 
 
 def _load_prefill_messages_script(config_data: dict) -> dict:
diff --git a/tests/test_webui_prefill_context.py b/tests/test_webui_prefill_context.py
index 26b9aca9..9c2b4aad 100644
--- a/tests/test_webui_prefill_context.py
+++ b/tests/test_webui_prefill_context.py
@@ -70,7 +70,7 @@ def test_webui_prefill_script_loads_json_messages(tmp_path):
     assert result["messages"] == [{"role": "system", "content": "Joplin has durable context; use notes/search tools for details."}]
 
 
-def test_webui_prefill_script_wraps_plain_text_for_any_notes_source(tmp_path):
+def test_webui_prefill_script_wraps_plain_text_as_user_context(tmp_path):
     from api.streaming import _load_webui_prefill_context
 
     script = tmp_path / "obsidian_recall.py"
@@ -80,7 +80,7 @@ def test_webui_prefill_script_wraps_plain_text_for_any_notes_source(tmp_path):
 
     assert result["status"] == "loaded"
     assert result["source"] == "script"
-    assert result["messages"] == [{"role": "system", "content": "Obsidian project note context"}]
+    assert result["messages"] == [{"role": "user", "content": "Obsidian project note context"}]
 
 
 def test_webui_prefill_script_errors_are_redacted(tmp_path):
@@ -111,7 +111,7 @@ def test_webui_prefill_script_takes_precedence_over_static_file(tmp_path):
     })
 
     assert result["source"] == "script"
-    assert result["messages"] == [{"role": "system", "content": "dynamic"}]
+    assert result["messages"] == [{"role": "user", "content": "dynamic"}]
 
 
 def test_webui_prefill_script_timeout_returns_redacted_error(tmp_path):