diff --git a/openviking/privacy/skill_placeholder.py b/openviking/privacy/skill_placeholder.py
index bc2ffabe40..d0879d7437 100644
--- a/openviking/privacy/skill_placeholder.py
+++ b/openviking/privacy/skill_placeholder.py
@@ -2,6 +2,7 @@
 # SPDX-License-Identifier: AGPL-3.0
 """Placeholder helpers for skill privacy values."""
 
+import re
 from dataclasses import dataclass, field
 
 
@@ -21,18 +22,6 @@ def _replace_structured_value(content: str, raw_value: str, placeholder: str) ->
     replacements = (
         (f'"{raw_value}"', f'"{placeholder}"'),
         (f"'{raw_value}'", f"'{placeholder}'"),
-        (f": {raw_value}\n", f": {placeholder}\n"),
-        (f": {raw_value}\r\n", f": {placeholder}\r\n"),
-        (f":{raw_value}\n", f":{placeholder}\n"),
-        (f":{raw_value}\r\n", f":{placeholder}\r\n"),
-        (f": {raw_value}", f": {placeholder}"),
-        (f":{raw_value}", f":{placeholder}"),
-        (f"= {raw_value}\n", f"= {placeholder}\n"),
-        (f"= {raw_value}\r\n", f"= {placeholder}\r\n"),
-        (f"={raw_value}\n", f"={placeholder}\n"),
-        (f"={raw_value}\r\n", f"={placeholder}\r\n"),
-        (f"= {raw_value}", f"= {placeholder}"),
-        (f"={raw_value}", f"={placeholder}"),
     )
 
     replaced = False
@@ -40,7 +29,20 @@ def _replace_structured_value(content: str, raw_value: str, placeholder: str) ->
         if old in content:
             content = content.replace(old, new)
             replaced = True
-    return content, replaced
+
+    bare_value_pattern = re.compile(
+        rf"(?P<separator>[:=])(?P<leading>[ \t]*){re.escape(raw_value)}"
+        r"(?P<trailing>[ \t]*)(?=\r?$)",
+        re.MULTILINE,
+    )
+    content, bare_replacement_count = bare_value_pattern.subn(
+        lambda match: (
+            f"{match.group('separator')}{match.group('leading')}"
+            f"{placeholder}{match.group('trailing')}"
+        ),
+        content,
+    )
+    return content, replaced or bare_replacement_count > 0
 
 
 def placeholderize_skill_content_with_blocks(
diff --git a/tests/server/test_privacy_config_service.py b/tests/server/test_privacy_config_service.py
index e4b8012621..d228577d7e 100644
--- a/tests/server/test_privacy_config_service.py
+++ b/tests/server/test_privacy_config_service.py
@@ -280,3 +280,29 @@ def test_placeholderization_replaces_all_structured_occurrences_for_same_value()
         'api_key: "{{ov_privacy:skill:multi-hit-skill:api_key}}"\n'
         "backup={{ov_privacy:skill:multi-hit-skill:api_key}}\n"
     )
+
+
+def test_placeholderization_preserves_crlf_spacing_and_regex_special_values():
+    result = placeholderize_skill_content_with_blocks(
+        "token:\ta.b+c?[x]  \r\ntext: a.b+c?[x] should stay here\r\n",
+        "regex-skill",
+        {"token": "a.b+c?[x]"},
+    )
+
+    assert result.replaced_values == {"token": "a.b+c?[x]"}
+    assert result.sanitized_content == (
+        "token:\t{{ov_privacy:skill:regex-skill:token}}  \r\ntext: a.b+c?[x] should stay here\r\n"
+    )
+
+
+def test_placeholderization_preserves_quoted_value_matching():
+    result = placeholderize_skill_content_with_blocks(
+        'note: use "secret" in prose\n',
+        "quoted-skill",
+        {"api_key": "secret"},
+    )
+
+    assert result.replaced_values == {"api_key": "secret"}
+    assert result.sanitized_content == (
+        'note: use "{{ov_privacy:skill:quoted-skill:api_key}}" in prose\n'
+    )