diff --git a/studio/backend/core/tool_healing.py b/studio/backend/core/tool_healing.py
index 4663512033..e91b541c0d 100644
--- a/studio/backend/core/tool_healing.py
+++ b/studio/backend/core/tool_healing.py
@@ -37,6 +37,10 @@ _TC_PARAM_CLOSE_RE = re.compile(r"\s*</parameter>\s*$")
 _GEMMA_QUOTE = '<|"|>'
 _PARAM_CLOSE_TAG = "</parameter>"
 _FUNC_CLOSE_TAG = "</function>"
+# A bare (unquoted) Gemma value ends at `}` or at a comma that begins the next
+# `key:` pair. A comma NOT followed by a key token is part of the value (e.g.
+# `location:New York, NY`), so it must not terminate the value.
+_GEMMA_NEXT_KEY_RE = re.compile(r"\s*[\w-]+\s*:")
 
 
 def _balanced_brace_end(
@@ -146,7 +150,14 @@ def _quote_gemma_object_keys(src: str) -> str:
             parts.append(src[ws:i])
             if i < len(src) and src[i] not in '"{[':
                 v_start = i
-                while i < len(src) and src[i] not in ",}":
+                # Consume the bare value up to `}` or a comma that starts the
+                # next key:value pair; a comma inside the value (e.g.
+                # `New York, NY`) does not terminate it.
+                while i < len(src):
+                    if src[i] == "}":
+                        break
+                    if src[i] == "," and _GEMMA_NEXT_KEY_RE.match(src, i + 1):
+                        break
                     i += 1
                 raw = src[v_start:i]
                 try:
@@ -196,6 +207,10 @@ def parse_tool_calls_from_text(
       <tool_call><function=web_search><parameter=query>...</parameter></function></tool_call>
     """
     tool_calls: list[dict] = []
+    # Byte spans already claimed by a parsed tool call. A tool-call marker that
+    # appears INSIDE another call's argument string is data, not a real call, so
+    # it must not be re-parsed into a spurious second call.
+    consumed: list[tuple[int, int]] = []
 
     for m in _TC_JSON_START_RE.finditer(content):
         brace_start = m.end() - 1
@@ -220,10 +235,13 @@ def parse_tool_calls_from_text(
             if isinstance(tc["function"]["arguments"], dict):
                 tc["function"]["arguments"] = json.dumps(tc["function"]["arguments"])
             tool_calls.append(tc)
+            consumed.append((m.start(), i + 1))
         except (json.JSONDecodeError, ValueError):
             pass
 
     for m in _TC_GEMMA_START_RE.finditer(content):
+        if any(start <= m.start() < end for start, end in consumed):
+            continue
         brace_start = m.end() - 1
         i = _balanced_brace_end(content, brace_start, gemma_quotes = True)
         if i < 0:
@@ -243,6 +261,7 @@ def parse_tool_calls_from_text(
                     },
                 }
             )
+            consumed.append((m.start(), i + 1))
         except (json.JSONDecodeError, ValueError):
             pass
 
diff --git a/studio/backend/routes/inference.py b/studio/backend/routes/inference.py
index 3ee0319a7d..5c88387e9b 100644
--- a/studio/backend/routes/inference.py
+++ b/studio/backend/routes/inference.py
@@ -9577,6 +9577,13 @@ async def _openai_passthrough_stream(
                                 delta = choice.get("delta")
                                 if isinstance(delta, dict) and delta.get("tool_calls"):
                                     saw_tool_call_delta = True
+                        # Detect an upstream error chunk independently of API
+                        # monitoring: when monitor_id is None (skip_api_monitor),
+                        # _monitor_openai_sse_line returns before inspecting the
+                        # error, so without this the synthetic-finish guard would
+                        # emit a successful finish_reason after a failed stream.
+                        if _monitor_openai_error_message(chunk_data):
+                            saw_stream_error = True
                     monitor_event = _monitor_openai_sse_line(
                         monitor_id,
                         raw_line,
diff --git a/studio/backend/tests/test_gemma_tool_parse_edge_cases.py b/studio/backend/tests/test_gemma_tool_parse_edge_cases.py
new file mode 100644
index 0000000000..45e3277a4b
--- /dev/null
+++ b/studio/backend/tests/test_gemma_tool_parse_edge_cases.py
@@ -0,0 +1,64 @@
+# SPDX-License-Identifier: AGPL-3.0-only
+# Copyright 2026-present the Unsloth AI Inc. team. All rights reserved. See /studio/LICENSE.AGPL-3.0
+
+"""Edge cases in Gemma-native tool-call parsing.
+
+Covers two failure modes:
+  1. A bare (unquoted) string argument that contains a comma, e.g.
+     ``location:New York, NY`` -- the comma must not be treated as the next
+     key boundary, or the whole call is dropped.
+  2. A tool-call marker that appears INSIDE another call's argument string is
+     data, not a real call, so it must not be promoted to a second tool call.
+"""
+
+from __future__ import annotations
+
+import json
+import sys
+from pathlib import Path
+
+_BACKEND_DIR = str(Path(__file__).resolve().parent.parent)
+if _BACKEND_DIR not in sys.path:
+    sys.path.insert(0, _BACKEND_DIR)
+
+from core.inference.tool_call_parser import parse_tool_calls_from_text
+
+
+def _args(call: dict) -> dict:
+    return json.loads(call["function"]["arguments"])
+
+
+def test_bare_string_argument_with_comma_is_kept():
+    calls = parse_tool_calls_from_text(
+        "<|tool_call>call:get_weather{location:New York, NY,unit:celsius}<tool_call|>"
+    )
+    assert len(calls) == 1, calls
+    assert calls[0]["function"]["name"] == "get_weather"
+    assert _args(calls[0]) == {"location": "New York, NY", "unit": "celsius"}
+
+
+def test_normal_multi_key_arguments_still_split():
+    calls = parse_tool_calls_from_text('<|tool_call>call:f{a:1,b:hello,c:"x,y"}<tool_call|>')
+    assert len(calls) == 1, calls
+    # Numbers stay numeric, bare strings get quoted, an explicit quoted comma
+    # stays inside its value.
+    assert _args(calls[0]) == {"a": 1, "b": "hello", "c": "x,y"}
+
+
+def test_marker_inside_json_argument_is_not_a_second_call():
+    # A python call whose `code` argument contains a Gemma marker string. The
+    # marker is data and must not execute as a second `terminal` call.
+    content = (
+        '<tool_call>{"name":"python","arguments":{"code":'
+        '"x = 1  # <|tool_call>call:terminal{command:ls}<tool_call|>"}}</tool_call>'
+    )
+    calls = parse_tool_calls_from_text(content)
+    assert [c["function"]["name"] for c in calls] == ["python"], calls
+
+
+def test_two_separate_gemma_calls_both_parse():
+    content = "<|tool_call>call:a{x:1}<tool_call|> and <|tool_call>call:b{y:2}<tool_call|>"
+    calls = parse_tool_calls_from_text(content)
+    assert [c["function"]["name"] for c in calls] == ["a", "b"], calls
+    assert _args(calls[0]) == {"x": 1}
+    assert _args(calls[1]) == {"y": 2}