diff --git a/agent/redact.py b/agent/redact.py
index 04d35e3c93602..a9ecd8bb1c7fa 100644
--- a/agent/redact.py
+++ b/agent/redact.py
@@ -15,7 +15,24 @@
 
 # Snapshot at import time so runtime env mutations (e.g. LLM-generated
 # `export HERMES_REDACT_SECRETS=false`) cannot disable redaction mid-session.
-_REDACT_ENABLED = os.getenv("HERMES_REDACT_SECRETS", "").lower() not in ("0", "false", "no", "off")
+#
+# Gateway mode always forces redaction on regardless of config, because
+# gateway serves multiple users over messaging platforms — leaking secrets
+# into LLM context risks reflecting them to any connected user.
+_IS_GATEWAY = os.getenv("HERMES_GATEWAY_SESSION", "").lower() in ("1", "true", "yes")
+_USER_DISABLED = os.getenv("HERMES_REDACT_SECRETS", "").lower() in ("0", "false", "no", "off")
+_REDACT_ENABLED = True if _IS_GATEWAY else not _USER_DISABLED
+
+if _USER_DISABLED and _IS_GATEWAY:
+    logger.warning(
+        "security.redact_secrets is set to false, but redaction is forced ON "
+        "in gateway mode to protect multi-user sessions."
+    )
+elif _USER_DISABLED:
+    logger.warning(
+        "Secret redaction is DISABLED (security.redact_secrets: false). "
+        "API keys and tokens will appear in plaintext in logs and tool output."
+    )
 
 # Known API key prefixes -- match the prefix + contiguous token chars
 _PREFIX_PATTERNS = [
diff --git a/gateway/run.py b/gateway/run.py
index 207ae120bae6e..ac21074dda741 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -197,7 +197,10 @@ def _ensure_ssl_certs() -> None:
         _tz_cfg = _cfg.get("timezone", "")
         if _tz_cfg and isinstance(_tz_cfg, str) and "HERMES_TIMEZONE" not in os.environ:
             os.environ["HERMES_TIMEZONE"] = _tz_cfg.strip()
-        # Security settings
+        # Security settings — gateway always forces redaction on to protect
+        # multi-user sessions.  The config value is still read so that
+        # redact.py can log a warning, but HERMES_GATEWAY_SESSION ensures
+        # _REDACT_ENABLED stays True regardless.
         _security_cfg = _cfg.get("security", {})
         if isinstance(_security_cfg, dict):
             _redact = _security_cfg.get("redact_secrets")
diff --git a/tests/agent/test_redact.py b/tests/agent/test_redact.py
index 83b1b4d1a1352..efede90ef0578 100644
--- a/tests/agent/test_redact.py
+++ b/tests/agent/test_redact.py
@@ -185,6 +185,47 @@ def test_url_without_key_unchanged(self):
         assert redact_sensitive_text(text) == text
 
 
+class TestGatewayForcesRedaction:
+    """Gateway mode must force redaction on even when config disables it."""
+
+    def test_gateway_overrides_disabled_redaction(self, monkeypatch):
+        """When HERMES_GATEWAY_SESSION=true, _REDACT_ENABLED must be True
+        even if HERMES_REDACT_SECRETS=false."""
+        monkeypatch.setenv("HERMES_GATEWAY_SESSION", "true")
+        monkeypatch.setenv("HERMES_REDACT_SECRETS", "false")
+        # Re-evaluate the module-level flag with the patched env
+        is_gateway = os.getenv("HERMES_GATEWAY_SESSION", "").lower() in ("1", "true", "yes")
+        user_disabled = os.getenv("HERMES_REDACT_SECRETS", "").lower() in ("0", "false", "no", "off")
+        enabled = True if is_gateway else not user_disabled
+        assert enabled is True
+
+    def test_gateway_env_variations(self, monkeypatch):
+        """All truthy values for HERMES_GATEWAY_SESSION should force redaction."""
+        for val in ("1", "true", "yes", "True", "YES"):
+            monkeypatch.setenv("HERMES_GATEWAY_SESSION", val)
+            monkeypatch.setenv("HERMES_REDACT_SECRETS", "false")
+            is_gateway = os.getenv("HERMES_GATEWAY_SESSION", "").lower() in ("1", "true", "yes")
+            assert is_gateway is True
+
+    def test_cli_mode_respects_disabled(self, monkeypatch):
+        """In CLI mode (no gateway), redact_secrets: false should take effect."""
+        monkeypatch.delenv("HERMES_GATEWAY_SESSION", raising=False)
+        monkeypatch.setenv("HERMES_REDACT_SECRETS", "false")
+        is_gateway = os.getenv("HERMES_GATEWAY_SESSION", "").lower() in ("1", "true", "yes")
+        user_disabled = os.getenv("HERMES_REDACT_SECRETS", "").lower() in ("0", "false", "no", "off")
+        enabled = True if is_gateway else not user_disabled
+        assert enabled is False
+
+    def test_redaction_active_by_default(self, monkeypatch):
+        """With no env vars set, redaction should be enabled."""
+        monkeypatch.delenv("HERMES_GATEWAY_SESSION", raising=False)
+        monkeypatch.delenv("HERMES_REDACT_SECRETS", raising=False)
+        is_gateway = os.getenv("HERMES_GATEWAY_SESSION", "").lower() in ("1", "true", "yes")
+        user_disabled = os.getenv("HERMES_REDACT_SECRETS", "").lower() in ("0", "false", "no", "off")
+        enabled = True if is_gateway else not user_disabled
+        assert enabled is True
+
+
 class TestRedactingFormatter:
     def test_formats_and_redacts(self):
         formatter = RedactingFormatter("%(message)s")
diff --git a/tests/tools/test_approval.py b/tests/tools/test_approval.py
index bbd11cd45ce58..ba4f5d1c11b9b 100644
--- a/tests/tools/test_approval.py
+++ b/tests/tools/test_approval.py
@@ -359,6 +359,16 @@ def test_tee_quoted_custom_hermes_home_env(self):
         assert dangerous is True
         assert key is not None
 
+    def test_tee_hermes_config_yaml(self):
+        dangerous, key, desc = detect_dangerous_command("echo x | tee ~/.hermes/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
+    def test_tee_custom_hermes_home_config_yaml(self):
+        dangerous, key, desc = detect_dangerous_command("echo x | tee $HERMES_HOME/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
     def test_tee_tmp_safe(self):
         dangerous, key, desc = detect_dangerous_command("echo hello | tee /tmp/output.txt")
         assert dangerous is False
@@ -370,6 +380,36 @@ def test_tee_local_file_safe(self):
         assert key is None
 
 
+class TestSensitiveRedirectConfigYaml:
+    """Detect shell redirection writes to ~/.hermes/config.yaml.
+
+    config.yaml contains security settings (redact_secrets, tirith, etc.)
+    that control the agent's own safety mechanisms. Writing to it should
+    require the same approval as writing to .env.
+    """
+
+    def test_redirect_to_hermes_config_yaml(self):
+        dangerous, key, desc = detect_dangerous_command("echo x > ~/.hermes/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
+    def test_redirect_to_custom_hermes_home_config(self):
+        dangerous, key, desc = detect_dangerous_command("echo x > $HERMES_HOME/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
+    def test_append_to_hermes_config_yaml(self):
+        dangerous, key, desc = detect_dangerous_command("echo x >> ~/.hermes/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
+    def test_redirect_to_unrelated_config_yaml_safe(self):
+        """config.yaml outside ~/.hermes/ should not be flagged."""
+        dangerous, key, desc = detect_dangerous_command("echo x > ./config.yaml")
+        assert dangerous is False
+        assert key is None
+
+
 class TestFindExecFullPathRm:
     """Detect find -exec with full-path rm bypasses."""
 
@@ -412,6 +452,11 @@ def test_append_to_tilde_ssh_authorized_keys(self):
         assert dangerous is True
         assert key is not None
 
+    def test_redirect_to_hermes_config_yaml(self):
+        dangerous, key, desc = detect_dangerous_command("echo x > ~/.hermes/config.yaml")
+        assert dangerous is True
+        assert key is not None
+
     def test_redirect_to_safe_tmp_file(self):
         dangerous, key, desc = detect_dangerous_command("echo hello > /tmp/output.txt")
         assert dangerous is False
diff --git a/tools/approval.py b/tools/approval.py
index 9a3a4ef260ee9..13f71e28e2268 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -62,10 +62,20 @@ def get_current_session_key(default: str = "default") -> str:
     r'(?:\$hermes_home|\$\{hermes_home\})/)'
     r'\.env\b'
 )
+# config.yaml contains security settings (redact_secrets, tirith, etc.)
+# that control the agent's own safety mechanisms — protect it the same
+# way we protect .env to prevent prompt injection from disabling guards.
+_HERMES_CONFIG_PATH = (
+    r'(?:~\/\.hermes/|'
+    r'(?:\$home|\$\{home\})/\.hermes/|'
+    r'(?:\$hermes_home|\$\{hermes_home\})/)'
+    r'config\.yaml\b'
+)
 _SENSITIVE_WRITE_TARGET = (
     r'(?:/etc/|/dev/sd|'
     rf'{_SSH_SENSITIVE_PATH}|'
-    rf'{_HERMES_ENV_PATH})'
+    rf'{_HERMES_ENV_PATH}|'
+    rf'{_HERMES_CONFIG_PATH})'
 )
 
 # =========================================================================