diff --git a/routstr/core/logging.py b/routstr/core/logging.py
index d682b944..0fb5fdcb 100644
--- a/routstr/core/logging.py
+++ b/routstr/core/logging.py
@@ -155,21 +155,26 @@ class SecurityFilter(logging.Filter):
         """Filter out sensitive information from log records."""
         try:
             message = record.getMessage()
+            standalone_patterns = [
+                        r"Bearer\s+([a-zA-Z0-9_\-\.]{10,})",       # Bearer token (must be 10 characters or more to reduce false-positives)
+                        r"cashu[A-Z]+([a-zA-Z0-9_\-\.=/+]+)",      # Cashu tokens
+                        r"nsec[a-z0-9]+"                    # Nostr Public / Private Key 
+                    ]
+            for pattern in standalone_patterns:
+                message = re.sub(
+                    pattern, f"[REDACTED]", message, flags=re.IGNORECASE
+                )
 
             for key in self.SENSITIVE_KEYS:
                 if key in message.lower():
-                    patterns = [
-                        rf"{key}[:\s=]+([a-zA-Z0-9_\-\.]+)",  # key: value or key=value
-                        rf'{key}[:\s=]+["\']([^"\']+)["\']',  # key: "value" or key='value'
-                        r"Bearer\s+([a-zA-Z0-9_\-\.]+)",  # Bearer token
-                        r"cashu[A-Z]+([a-zA-Z0-9_\-\.=/+]+)",  # Cashu tokens
+                    key_patterns = [
+                        rf'{key}\s*[:=]\s*([a-zA-Z0-9_\-\.=/+]+)', # key:value or key=value (including any variant with spaces)
+                        rf'{key}\s*[:=]\s*["\']([^"\']+)["\']',    # key:"value" or key='value' (including any variant with spaces)
                     ]
-
-                    for pattern in patterns:
+                    for pattern in key_patterns:
                         message = re.sub(
                             pattern, f"{key}: [REDACTED]", message, flags=re.IGNORECASE
                         )
-
             record.msg = message
             record.args = ()
 
diff --git a/tests/unit/test_logging_securityfilter.py b/tests/unit/test_logging_securityfilter.py
new file mode 100644
index 00000000..d73e89bf
--- /dev/null
+++ b/tests/unit/test_logging_securityfilter.py
@@ -0,0 +1,112 @@
+"""Unit tests for the logging SecurityFilter.
+
+This module tests that the SecurityFilter correctly identifies and redacts
+sensitive information from log messages without causing false positives.
+
+"""
+
+import logging
+import pytest
+
+from routstr.core.logging import SecurityFilter
+
+
+@pytest.fixture
+def security_filter() -> SecurityFilter:
+    """Provide an instance of the SecurityFilter for testing."""
+    return SecurityFilter()
+
+
+@pytest.fixture
+def filter_message(security_filter: SecurityFilter):
+    """A helper fixture to apply the filter to a message string."""
+    def _filter(msg: str) -> str:
+        record = logging.LogRecord(
+            name="test_logger",
+            level=logging.INFO,
+            pathname="",
+            lineno=0,
+            msg=msg,
+            args=(),
+            exc_info=None,
+        )
+        security_filter.filter(record)
+        return record.getMessage()
+    return _filter
+
+
+def test_redacts_unquoted_key_value_pairs(filter_message) -> None:
+    """Test that an unquoted key-value pair is correctly redacted."""
+    original = "Processing request with api_key=sk-12345abcdef"
+    expected = "Processing request with api_key: [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_redacts_quoted_key_value_pairs(filter_message) -> None:
+    """Test that a quoted token is correctly redacted."""
+    original = 'User authenticated with token="cashuA123abc"'
+    expected = 'User authenticated with token: [REDACTED]'
+    assert filter_message(original) == expected
+
+
+def test_redacts_bearer_token(filter_message) -> None:
+    """Test that a Bearer token of sufficient length is redacted."""
+    original = "Authorization: Bearer abc1234567890xyzabcdefg"
+    expected = "Authorization: [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_redacts_cashu_token(filter_message) -> None:
+    """Test that a Cashu token is redacted."""
+    original = "Received cashuTOKENeyJ0b2tlbiI6W3siaWQiOiI"
+    expected = "Received [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_redacts_nsec_key(filter_message) -> None:
+    """Test that a full-length Nostr private key is redacted."""
+    original = "Private key is nsec1a8d9f8s7d9f8a7s6d5f4a3s2d1f9a8s7d6f5a4s3d2f1a9s8d7f6a5s4d3f"
+    expected = "Private key is [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_ignores_non_sensitive_message(filter_message) -> None:
+    """Test that a message with no sensitive data is left untouched."""
+    original = "No token pricing configured, using base cost"
+    expected = "No token pricing configured, using base cost"
+    assert filter_message(original) == expected
+
+
+def test_multiple_secrets_in_one_message(filter_message) -> None:
+    """Test that multiple different secrets in one message are all redacted."""
+    original = 'Auth with Bearer abcdefghijklmnopqrstuvwxyz and api_key="sk-12345"'
+    expected = "Auth with [REDACTED] and api_key: [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_redacts_key_with_no_value(filter_message) -> None:
+    """Test that a key with no value is not redacted."""
+    original = "Request contains api_key and secret."
+    expected = "Request contains api_key and secret."
+    assert filter_message(original) == expected
+
+
+def test_redacts_key_value_with_spaces(filter_message) -> None:
+    """Test that key-value pairs with extra spaces are correctly redacted."""
+    original = "Auth info:   api_key   =   'sk-12345'"
+    expected = "Auth info:   api_key: [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_is_case_insensitive_for_keys(filter_message) -> None:
+    """Test that key matching is case-insensitive."""
+    original = "TOKEN=sk-abcdef12345"
+    expected = "token: [REDACTED]"
+    assert filter_message(original) == expected
+
+
+def test_is_case_insensitive_for_standalone(filter_message) -> None:
+    """Test that standalone matching is case-insensitive."""
+    original = "Using NSEC1a8d9f8s7d9f8a7s6d5f4a3s2d1f9a8s7d6f5a4s3d2f1a9s8d7f6a5s4d3f and CaShuA123abc"
+    expected = "Using [REDACTED] and [REDACTED]"
+    assert filter_message(original) == expected
\ No newline at end of file