diff --git a/src/openhuman/tinyagents/middleware.rs b/src/openhuman/tinyagents/middleware.rs
index b0a0537067..a3b30cfa58 100644
--- a/src/openhuman/tinyagents/middleware.rs
+++ b/src/openhuman/tinyagents/middleware.rs
@@ -1403,6 +1403,25 @@ impl Middleware<()> for ToolOutcomeCaptureMiddleware {
         _state: &(),
         result: &mut TaToolResult,
     ) -> TaResult<()> {
+        // Enrich a raw security-policy / autonomy block (issue #4094): the ~20
+        // `[policy-blocked]` denials emitted deep in `SecurityPolicy` / the tools
+        // return a bare marker line with no workaround and no relay directive, so
+        // the agent dead-ends. Rewrite the content into the structured
+        // `Blocked / Reason / Workaround / relay` shape here — the last `after_tool`
+        // hook, so the enriched text is what the transcript keeps. The marker is
+        // preserved, and already-structured `ToolPolicyMiddleware` denials (which
+        // carry a `Workaround:` suffix) are left untouched. This runs before
+        // classification below, which still recognises the preserved marker.
+        if let Some(enriched) =
+            super::policy_denial::maybe_enrich_policy_block(&result.name, &result.content)
+        {
+            tracing::debug!(
+                tool = result.name.as_str(),
+                "[tinyagents::mw] enriched raw security-policy block with workaround + relay"
+            );
+            result.content = enriched;
+        }
+
         let success = result.error.is_none();
         // Classify the failure so the live `ToolCallCompleted` event and the
         // persisted timeline can explain it in plain language. A hard
@@ -1923,6 +1942,52 @@ mod tests {
         }
     }
 
+    // ── ToolOutcomeCaptureMiddleware policy-block enrichment (issue #4094) ───
+
+    fn outcome_capture_mw() -> ToolOutcomeCaptureMiddleware {
+        ToolOutcomeCaptureMiddleware::new(
+            std::sync::Arc::new(std::sync::Mutex::new(Vec::new())),
+            std::sync::Arc::new(std::sync::Mutex::new(std::collections::HashMap::new())),
+        )
+    }
+
+    #[tokio::test]
+    async fn raw_security_policy_block_is_enriched_with_workaround_and_relay() {
+        let mw = outcome_capture_mw();
+        let mut result = tool_result(
+            "run_command",
+            "[policy-blocked] Security policy: read-only mode — only read commands are allowed",
+        );
+        result.error = Some(result.content.clone());
+        mw.after_tool(&mut ctx(), &(), &mut result).await.unwrap();
+        // The bare denial now carries a workaround + relay directive, and keeps the
+        // marker so classification / the loop-breaker still recognise it.
+        assert!(result.content.contains("Workaround:"), "{}", result.content);
+        assert!(result.content.contains("Relay this to the user"));
+        assert!(result
+            .content
+            .contains(crate::openhuman::security::POLICY_BLOCKED_MARKER));
+        assert!(result.content.contains("read-only mode"));
+    }
+
+    #[tokio::test]
+    async fn already_structured_denial_is_not_double_wrapped() {
+        // A ToolPolicyMiddleware-style denial already has "Workaround:"; the capture
+        // middleware must leave it untouched (no second Workaround block).
+        let mw = outcome_capture_mw();
+        let structured =
+            "Blocked: Tool 'x' denied. Reason: nope. Workaround: do y. Relay this to the user: ...";
+        let mut result = tool_result("x", structured);
+        result.error = Some(result.content.clone());
+        mw.after_tool(&mut ctx(), &(), &mut result).await.unwrap();
+        assert_eq!(
+            result.content.matches("Workaround:").count(),
+            1,
+            "must not double-wrap: {}",
+            result.content
+        );
+    }
+
     // ── TurnContextMiddleware config ────────────────────────────────────────
 
     #[test]
diff --git a/src/openhuman/tinyagents/policy_denial.rs b/src/openhuman/tinyagents/policy_denial.rs
index 33db2f7596..ccf70d9371 100644
--- a/src/openhuman/tinyagents/policy_denial.rs
+++ b/src/openhuman/tinyagents/policy_denial.rs
@@ -9,11 +9,29 @@
 //! flows back into the turn the same way the unknown-tool corrective error is
 //! surfaced to the model (see PR #4360).
 
+use crate::openhuman::security::POLICY_BLOCKED_MARKER;
 use crate::openhuman::tools::PermissionLevel;
 
+/// Generic workaround for a raw security-policy / autonomy block. These denials
+/// originate deep in the tools / `SecurityPolicy` layer (autonomy tier, command
+/// classification, path checks) rather than the pluggable `ToolPolicy`, so there
+/// is no single structured reason to lean on — point the agent at the levers that
+/// actually unblock the family.
+const SECURITY_POLICY_WORKAROUND: &str = "Raise the agent's access tier / autonomy \
+    (Settings → Agent access, or the `config.update_autonomy_settings` RPC / \
+    `[autonomy]` config) if this action should be allowed; otherwise reach the goal \
+    with a permitted (e.g. read-only) alternative, or report that it can't be done \
+    here.";
+
 /// The boundary that blocked a tool call, with the context needed to explain it
 /// and suggest a way forward.
 pub(super) enum PolicyDenial<'a> {
+    /// A raw security-policy / autonomy denial emitted by the tools /
+    /// `SecurityPolicy` layer, recognised by its [`POLICY_BLOCKED_MARKER`] prefix.
+    /// It already states *what* and *why* but carries no workaround or relay
+    /// directive; [`render`](Self::render) keeps the marker and reason and appends
+    /// the missing guidance. `raw_reason` is the full marker-bearing tool output.
+    SecurityPolicyBlocked { tool: &'a str, raw_reason: &'a str },
     /// The session tool policy forbids this tool for the channel's permission
     /// tier (it is not in the allowed set).
     SessionForbidden {
@@ -57,6 +75,24 @@ impl PolicyDenial<'_> {
     /// message for the model.
     pub(super) fn render(&self) -> String {
         let (blocked, reason, workaround) = match self {
+            PolicyDenial::SecurityPolicyBlocked { tool, raw_reason } => {
+                // Strip the marker prefix from the reason (it is re-added on the
+                // `blocked` line so downstream `contains(POLICY_BLOCKED_MARKER)`
+                // checks — classification, the loop-breaker — keep matching).
+                let reason = raw_reason
+                    .trim()
+                    .strip_prefix(POLICY_BLOCKED_MARKER)
+                    .unwrap_or(raw_reason)
+                    .trim()
+                    .to_string();
+                (
+                    format!(
+                        "{POLICY_BLOCKED_MARKER} Tool '{tool}' was blocked by the security policy"
+                    ),
+                    reason,
+                    SECURITY_POLICY_WORKAROUND.to_string(),
+                )
+            }
             PolicyDenial::SessionForbidden {
                 tool,
                 required,
@@ -125,6 +161,33 @@ impl PolicyDenial<'_> {
     }
 }
 
+/// Enrich a raw security-policy / autonomy tool result (issue #4094).
+///
+/// The pluggable-`ToolPolicy` and channel-permission denials are already rendered
+/// with a `Blocked / Reason / Workaround / relay` shape by [`ToolPolicyMiddleware`]
+/// (PR #4443). But the ~20 `[policy-blocked]` denials emitted deep in
+/// `SecurityPolicy` / the tools themselves still return a bare marker line with no
+/// workaround and no relay directive, so the agent dead-ends. This wraps such a
+/// result into the structured form, appending the workaround + relay while keeping
+/// the marker (so classification and the repeated-failure breaker still match).
+///
+/// Returns `None` — leaving the content untouched — when the result is not a raw
+/// policy block, i.e. it lacks the marker, or it already carries a `Workaround:`
+/// suffix (an already-structured `ToolPolicyMiddleware` denial that must not be
+/// double-wrapped).
+pub(super) fn maybe_enrich_policy_block(tool: &str, content: &str) -> Option<String> {
+    if !content.contains(POLICY_BLOCKED_MARKER) || content.contains("Workaround:") {
+        return None;
+    }
+    Some(
+        PolicyDenial::SecurityPolicyBlocked {
+            tool,
+            raw_reason: content,
+        }
+        .render(),
+    )
+}
+
 /// Workaround shared by the permission-tier denials: raise the channel's
 /// agent-access tier, or fall back to a lower-permission tool.
 fn raise_tier_workaround(
@@ -215,6 +278,50 @@ mod tests {
         assert!(msg.contains("Relay this to the user"));
     }
 
+    #[test]
+    fn security_policy_block_keeps_marker_and_adds_workaround_and_relay() {
+        let raw =
+            "[policy-blocked] Security policy: read-only mode — only read commands are allowed";
+        let msg = PolicyDenial::SecurityPolicyBlocked {
+            tool: "run_command",
+            raw_reason: raw,
+        }
+        .render();
+
+        // The marker survives so classification + the loop-breaker still match.
+        assert!(msg.contains(POLICY_BLOCKED_MARKER));
+        assert!(msg.starts_with("Blocked:"));
+        // The original reason is preserved (without a duplicated marker in it).
+        assert!(msg.contains("read-only mode — only read commands are allowed"));
+        assert!(msg.contains("Workaround:"));
+        assert!(msg.contains("agent-access tier / autonomy") || msg.contains("Agent access"));
+        assert!(msg.contains("Relay this to the user"));
+    }
+
+    #[test]
+    fn maybe_enrich_only_touches_raw_marker_results() {
+        // A raw marker line with no workaround → enriched.
+        let raw = "[policy-blocked] Command not allowed by security policy: rm -rf /";
+        let enriched = maybe_enrich_policy_block("run_command", raw)
+            .expect("a raw policy block should be enriched");
+        assert!(enriched.contains("Workaround:"));
+        assert!(enriched.contains("Relay this to the user"));
+        assert!(enriched.contains(POLICY_BLOCKED_MARKER));
+
+        // An already-structured ToolPolicyMiddleware denial (has "Workaround:") is
+        // left alone — no double-wrapping.
+        let already = PolicyDenial::PolicyDenied {
+            tool: "run_script",
+            policy: "sandbox",
+            reason: "sandbox restriction",
+        }
+        .render();
+        assert!(maybe_enrich_policy_block("run_script", &already).is_none());
+
+        // A plain non-policy error is untouched.
+        assert!(maybe_enrich_policy_block("read_file", "Error: file not found").is_none());
+    }
+
     #[test]
     fn approval_required_suggests_approval_then_retry() {
         let msg = PolicyDenial::ApprovalRequired {
diff --git a/tests/config_auth_app_state_connectivity_e2e.rs b/tests/config_auth_app_state_connectivity_e2e.rs
index 266d46584c..802855f2fe 100644
--- a/tests/config_auth_app_state_connectivity_e2e.rs
+++ b/tests/config_auth_app_state_connectivity_e2e.rs
@@ -2802,6 +2802,7 @@ async fn worker_a_controller_schemas_are_fully_exposed() {
                 "openhuman.config_get_meet_settings",
                 "openhuman.config_get_memory_sync_settings",
                 "openhuman.config_get_onboarding_completed",
+                "openhuman.config_get_privacy_mode",
                 "openhuman.config_get_runtime_flags",
                 "openhuman.config_get_sandbox_settings",
                 "openhuman.config_get_search_settings",
@@ -2811,6 +2812,7 @@ async fn worker_a_controller_schemas_are_fully_exposed() {
                 "openhuman.config_resolve_api_url",
                 "openhuman.config_set_browser_allow_all",
                 "openhuman.config_set_onboarding_completed",
+                "openhuman.config_set_privacy_mode",
                 "openhuman.config_set_super_context_enabled",
                 "openhuman.config_update_activity_level_settings",
                 "openhuman.config_update_agent_paths",