diff --git a/src/agent/agent_loop.rs b/src/agent/agent_loop.rs
index 1780ba9d..4282daa5 100644
--- a/src/agent/agent_loop.rs
+++ b/src/agent/agent_loop.rs
@@ -146,6 +146,8 @@ pub struct AgentDeps {
     pub transcription: Option<Arc<crate::transcription::TranscriptionMiddleware>>,
     /// Document text extraction middleware for PDF, DOCX, PPTX, etc.
     pub document_extraction: Option<Arc<crate::document_extraction::DocumentExtractionMiddleware>>,
+    /// Sandbox readiness state for full-job routine dispatch.
+    pub sandbox_readiness: crate::agent::routine_engine::SandboxReadiness,
     /// Software builder for self-repair tool rebuilding.
     pub builder: Option<Arc<dyn crate::tools::SoftwareBuilder>>,
 }
@@ -556,6 +558,7 @@ impl Agent {
                         Some(self.scheduler.clone()),
                         self.tools().clone(),
                         self.safety().clone(),
+                        self.deps.sandbox_readiness,
                     ));
 
                     // Register routine tools
diff --git a/src/agent/dispatcher.rs b/src/agent/dispatcher.rs
index d3825b2f..0b47c928 100644
--- a/src/agent/dispatcher.rs
+++ b/src/agent/dispatcher.rs
@@ -1199,6 +1199,7 @@ mod tests {
             http_interceptor: None,
             transcription: None,
             document_extraction: None,
+            sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
         };
 
@@ -2070,6 +2071,7 @@ mod tests {
             http_interceptor: None,
             transcription: None,
             document_extraction: None,
+            sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
         };
 
@@ -2189,6 +2191,7 @@ mod tests {
                 http_interceptor: None,
                 transcription: None,
                 document_extraction: None,
+                sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
                 builder: None,
             };
 
diff --git a/src/agent/mod.rs b/src/agent/mod.rs
index ee980233..81c56dad 100644
--- a/src/agent/mod.rs
+++ b/src/agent/mod.rs
@@ -39,7 +39,7 @@ pub use context_monitor::{CompactionStrategy, ContextBreakdown, ContextMonitor};
 pub use heartbeat::{HeartbeatConfig, HeartbeatResult, HeartbeatRunner, spawn_heartbeat};
 pub use router::{MessageIntent, Router};
 pub use routine::{Routine, RoutineAction, RoutineRun, Trigger};
-pub use routine_engine::RoutineEngine;
+pub use routine_engine::{RoutineEngine, SandboxReadiness};
 pub use scheduler::Scheduler;
 pub use self_repair::{BrokenTool, RepairResult, RepairTask, SelfRepair, StuckJob};
 pub use session::{PendingApproval, PendingAuth, Session, Thread, ThreadState, Turn, TurnState};
diff --git a/src/agent/routine_engine.rs b/src/agent/routine_engine.rs
index 6e216fdc..a4f35ccb 100644
--- a/src/agent/routine_engine.rs
+++ b/src/agent/routine_engine.rs
@@ -44,6 +44,17 @@ enum EventMatcher {
     System { routine: Routine },
 }
 
+/// Distinguishes why sandbox is unavailable so error messages are accurate.
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum SandboxReadiness {
+    /// Docker is available and sandbox is enabled.
+    Available,
+    /// User explicitly disabled sandboxing (SANDBOX_ENABLED=false).
+    DisabledByConfig,
+    /// Sandbox is enabled but Docker is not running or not installed.
+    DockerUnavailable,
+}
+
 /// The routine execution engine.
 pub struct RoutineEngine {
     config: RoutineConfig,
@@ -62,6 +73,8 @@ pub struct RoutineEngine {
     tools: Arc<ToolRegistry>,
     /// Safety layer for tool output sanitization.
     safety: Arc<SafetyLayer>,
+    /// Sandbox readiness state for full-job dispatch.
+    sandbox_readiness: SandboxReadiness,
     /// Timestamp when this engine instance was created. Used by
     /// `sync_dispatched_runs` to distinguish orphaned runs (from a previous
     /// process) from actively-watched runs (from this process).
@@ -79,6 +92,7 @@ impl RoutineEngine {
         scheduler: Option<Arc<Scheduler>>,
         tools: Arc<ToolRegistry>,
         safety: Arc<SafetyLayer>,
+        sandbox_readiness: SandboxReadiness,
     ) -> Self {
         Self {
             config,
@@ -91,6 +105,7 @@ impl RoutineEngine {
             scheduler,
             tools,
             safety,
+            sandbox_readiness,
             boot_time: Utc::now(),
         }
     }
@@ -689,6 +704,7 @@ impl RoutineEngine {
             scheduler: self.scheduler.clone(),
             tools: self.tools.clone(),
             safety: self.safety.clone(),
+            sandbox_readiness: self.sandbox_readiness,
         };
 
         tokio::spawn(async move {
@@ -724,6 +740,7 @@ impl RoutineEngine {
             scheduler: self.scheduler.clone(),
             tools: self.tools.clone(),
             safety: self.safety.clone(),
+            sandbox_readiness: self.sandbox_readiness,
         };
 
         // Record the run in DB, then spawn execution
@@ -860,6 +877,7 @@ struct EngineContext {
     scheduler: Option<Arc<Scheduler>>,
     tools: Arc<ToolRegistry>,
     safety: Arc<SafetyLayer>,
+    sandbox_readiness: SandboxReadiness,
 }
 
 /// Execute a routine run. Handles both lightweight and full_job modes.
@@ -1040,6 +1058,24 @@ async fn execute_full_job(
     run: &RoutineRun,
     execution: &FullJobExecutionConfig<'_>,
 ) -> Result<(RunStatus, Option<String>, Option<i32>), RoutineError> {
+    match ctx.sandbox_readiness {
+        SandboxReadiness::Available => {}
+        SandboxReadiness::DisabledByConfig => {
+            return Err(RoutineError::JobDispatchFailed {
+                reason: "Sandboxing is disabled (SANDBOX_ENABLED=false). \
+                         Full-job routines require sandbox."
+                    .to_string(),
+            });
+        }
+        SandboxReadiness::DockerUnavailable => {
+            return Err(RoutineError::JobDispatchFailed {
+                reason: "Sandbox is enabled but Docker is not available. \
+                         Install Docker or set SANDBOX_ENABLED=false."
+                    .to_string(),
+            });
+        }
+    }
+
     let scheduler = ctx
         .scheduler
         .as_ref()
@@ -1710,6 +1746,7 @@ pub fn spawn_cron_ticker(
             // never races with FullJobWatcher instances from this process.
             engine.sync_dispatched_runs().await;
             engine.check_cron_triggers().await;
+            engine.sync_dispatched_runs().await;
         }
     })
 }
@@ -1723,6 +1760,56 @@ fn truncate(s: &str, max: usize) -> String {
     }
 }
 
+/// Sanitize a summary string from job transitions before using in notifications.
+///
+/// `last_reason` comes from untrusted container code, so we:
+/// 1. Strip control characters (except newline) to prevent terminal injection
+/// 2. Strip HTML tags to prevent injection in web-rendered notifications
+/// 3. Collapse multiple whitespace/newlines to single spaces for cleaner output
+/// 4. Truncate to 500 chars to prevent oversized notifications
+#[cfg(test)]
+fn sanitize_summary(s: &str) -> String {
+    // Strip control characters (keep newline for now, collapse later)
+    let no_control: String = s
+        .chars()
+        .filter(|c| !c.is_control() || *c == '\n')
+        .collect();
+
+    // Strip HTML tags (e.g. <script>, <img>, <a href=...>)
+    let no_html = strip_html_tags(&no_control);
+
+    // Collapse whitespace: multiple spaces/newlines become a single space
+    let collapsed: String = no_html.split_whitespace().collect::<Vec<_>>().join(" ");
+
+    // Truncate to reasonable length
+    if collapsed.len() <= 500 {
+        collapsed
+    } else {
+        // Find a safe char boundary for truncation
+        let mut end = 500;
+        while !collapsed.is_char_boundary(end) && end > 0 {
+            end -= 1;
+        }
+        format!("{}...", &collapsed[..end])
+    }
+}
+
+/// Remove HTML/XML tags from a string.
+#[cfg(test)]
+fn strip_html_tags(s: &str) -> String {
+    let mut result = String::with_capacity(s.len());
+    let mut in_tag = false;
+    for c in s.chars() {
+        match c {
+            '<' => in_tag = true,
+            '>' if in_tag => in_tag = false,
+            _ if !in_tag => result.push(c),
+            _ => {}
+        }
+    }
+    result
+}
+
 #[cfg(test)]
 mod tests {
     use crate::agent::routine::{NotifyConfig, RunStatus};
@@ -2004,6 +2091,62 @@ mod tests {
         assert_eq!(snapshot[2].content, "b"); // safety: test-only no-panics CI false positive
     }
 
+    #[test]
+    fn test_running_status_does_not_notify() {
+        let config = NotifyConfig {
+            on_success: true,
+            on_failure: true,
+            on_attention: true,
+            ..Default::default()
+        };
+        let should_notify = match RunStatus::Running {
+            RunStatus::Ok => config.on_success,
+            RunStatus::Attention => config.on_attention,
+            RunStatus::Failed => config.on_failure,
+            RunStatus::Running => false,
+        };
+        assert!(!should_notify);
+    }
+
+    #[test]
+    fn test_full_job_dispatch_returns_running_status() {
+        assert_eq!(RunStatus::Running.to_string(), "running");
+    }
+
+    #[test]
+    fn test_sandbox_readiness_disabled_by_config_error() {
+        use super::SandboxReadiness;
+
+        let readiness = SandboxReadiness::DisabledByConfig;
+        assert_ne!(readiness, SandboxReadiness::Available);
+
+        let err = crate::error::RoutineError::JobDispatchFailed {
+            reason: "Sandboxing is disabled (SANDBOX_ENABLED=false). \
+                     Full-job routines require sandbox."
+                .to_string(),
+        };
+        let msg = err.to_string();
+        assert!(msg.contains("SANDBOX_ENABLED=false"));
+        assert!(msg.contains("require sandbox"));
+    }
+
+    #[test]
+    fn test_sandbox_readiness_docker_unavailable_error() {
+        use super::SandboxReadiness;
+
+        let readiness = SandboxReadiness::DockerUnavailable;
+        assert_ne!(readiness, SandboxReadiness::Available);
+
+        let err = crate::error::RoutineError::JobDispatchFailed {
+            reason: "Sandbox is enabled but Docker is not available. \
+                     Install Docker or set SANDBOX_ENABLED=false."
+                .to_string(),
+        };
+        let msg = err.to_string();
+        assert!(msg.contains("Docker is not available"));
+        assert!(msg.contains("SANDBOX_ENABLED"));
+    }
+
     /// Regression test for #1317: FullJobWatcher maps terminal job states correctly.
     #[test]
     fn test_full_job_watcher_state_mapping() {
@@ -2085,4 +2228,50 @@ mod tests {
             );
         }
     }
+
+    #[test]
+    fn test_sanitize_summary_strips_control_chars() {
+        use super::sanitize_summary;
+
+        // Preserves normal text
+        assert_eq!(sanitize_summary("Job completed"), "Job completed");
+
+        // Strips control characters and collapses whitespace
+        assert_eq!(
+            sanitize_summary("line1\nline2\x00\x1b[31mred"),
+            "line1 line2[31mred"
+        );
+
+        // Truncates long strings
+        let long = "x".repeat(600);
+        let result = sanitize_summary(&long);
+        assert!(result.len() <= 503); // 500 + "..."
+        assert!(result.ends_with("..."));
+    }
+
+    #[test]
+    fn test_sanitize_summary_strips_html() {
+        use super::sanitize_summary;
+
+        assert_eq!(
+            sanitize_summary("Hello <script>alert('xss')</script> world"),
+            "Hello alert('xss') world"
+        );
+        assert_eq!(
+            sanitize_summary("<b>bold</b> and <a href=\"evil\">link</a>"),
+            "bold and link"
+        );
+        assert_eq!(sanitize_summary("<img src=x onerror=alert(1)>"), "");
+    }
+
+    #[test]
+    fn test_sanitize_summary_multibyte_truncation() {
+        use super::sanitize_summary;
+
+        // Ensure truncation doesn't panic on multi-byte chars near the boundary
+        let s = "a".repeat(498) + "\u{1F600}\u{1F600}"; // 498 + two 4-byte emoji
+        let result = sanitize_summary(&s);
+        assert!(result.len() <= 503);
+        assert!(result.ends_with("..."));
+    }
 }
diff --git a/src/db/mod.rs b/src/db/mod.rs
index 49287308..f1e8c276 100644
--- a/src/db/mod.rs
+++ b/src/db/mod.rs
@@ -525,6 +525,7 @@ pub trait RoutineStore: Send + Sync {
         run_id: Uuid,
         job_id: Uuid,
     ) -> Result<(), DatabaseError>;
+
     /// List routine runs that were dispatched as full_job but have not yet
     /// been finalized (status='running' with a linked job_id).
     async fn list_dispatched_routine_runs(&self) -> Result<Vec<RoutineRun>, DatabaseError>;
diff --git a/src/main.rs b/src/main.rs
index e7477bc3..9c482e1b 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -272,6 +272,21 @@ async fn async_main() -> anyhow::Result<()> {
     let prompt_queue = orch.prompt_queue;
     let docker_status = orch.docker_status;
 
+    // Derive user-facing warning from docker_status for channel notification
+    let docker_user_warning: Option<String> = match docker_status {
+        ironclaw::sandbox::DockerStatus::NotInstalled => Some(
+            "Sandbox is enabled but Docker is not installed -- \
+             full_job routines will fail until Docker is available."
+                .to_string(),
+        ),
+        ironclaw::sandbox::DockerStatus::NotRunning => Some(
+            "Sandbox is enabled but Docker is not running -- \
+             full_job routines will fail until Docker is started."
+                .to_string(),
+        ),
+        _ => None,
+    };
+
     // ── Channel setup ──────────────────────────────────────────────────
 
     let channels = ChannelManager::new();
@@ -748,9 +763,17 @@ async fn async_main() -> anyhow::Result<()> {
         document_extraction: Some(Arc::new(
             ironclaw::document_extraction::DocumentExtractionMiddleware::new(),
         )),
+        sandbox_readiness: if !config.sandbox.enabled {
+            ironclaw::agent::routine_engine::SandboxReadiness::DisabledByConfig
+        } else if docker_status.is_ok() {
+            ironclaw::agent::routine_engine::SandboxReadiness::Available
+        } else {
+            ironclaw::agent::routine_engine::SandboxReadiness::DockerUnavailable
+        },
         builder: components.builder,
     };
 
+    let channels_for_warnings = Arc::clone(&channels);
     let mut agent = Agent::new(
         config.agent.clone(),
         deps,
@@ -957,6 +980,27 @@ async fn async_main() -> anyhow::Result<()> {
         });
     }
 
+    // Notify user if sandbox is unavailable (Docker missing/not running)
+    if let Some(warning) = docker_user_warning {
+        let channels_ref = Arc::clone(&channels_for_warnings);
+        tokio::spawn(async move {
+            // Delay to let channels finish connecting before sending the warning.
+            // 5s is generous but avoids the message being lost on slow startups.
+            tokio::time::sleep(std::time::Duration::from_secs(5)).await;
+            tracing::debug!("Sending sandbox-unavailable warning to connected channels");
+            let response = ironclaw::channels::OutgoingResponse {
+                content: format!("Warning: {warning}"),
+                thread_id: None,
+                attachments: Vec::new(),
+                metadata: serde_json::json!({
+                    "source": "system",
+                    "type": "warning",
+                }),
+            };
+            let _ = channels_ref.broadcast_all("default", response).await;
+        });
+    }
+
     agent.run().await?;
 
     // ── Shutdown ────────────────────────────────────────────────────────
diff --git a/src/testing/mod.rs b/src/testing/mod.rs
index d5504393..953cbfcd 100644
--- a/src/testing/mod.rs
+++ b/src/testing/mod.rs
@@ -492,6 +492,7 @@ impl TestHarnessBuilder {
             http_interceptor: None,
             transcription: None,
             document_extraction: None,
+            sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
         };
 
diff --git a/tests/e2e_routine_heartbeat.rs b/tests/e2e_routine_heartbeat.rs
index 116dd1e0..b467c9c8 100644
--- a/tests/e2e_routine_heartbeat.rs
+++ b/tests/e2e_routine_heartbeat.rs
@@ -20,7 +20,7 @@ mod tests {
         RunStatus, Trigger,
     };
     use ironclaw::agent::routine_engine::RoutineEngine;
-    use ironclaw::agent::{HeartbeatConfig, HeartbeatRunner, Scheduler};
+    use ironclaw::agent::{HeartbeatConfig, HeartbeatRunner, SandboxReadiness, Scheduler};
     use ironclaw::channels::IncomingMessage;
     use ironclaw::config::{AgentConfig, RoutineConfig, SafetyConfig};
     use ironclaw::context::{ContextManager, JobContext};
@@ -266,6 +266,7 @@ mod tests {
             Some(scheduler),
             registry,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ))
     }
 
@@ -346,6 +347,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         // Insert a cron routine with next_fire_at in the past.
@@ -423,6 +425,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         // Insert an event routine matching "deploy.*production".
@@ -516,6 +519,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         let routine = make_routine(
@@ -623,6 +627,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         let mut filters = std::collections::HashMap::new();
@@ -764,6 +769,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         // Insert an event routine with 1-hour cooldown.
@@ -949,6 +955,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         (engine, db, dir)
@@ -1078,6 +1085,7 @@ mod tests {
             None, // no scheduler — rejected before dispatch
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         // Create a full_job routine with max_concurrent = 1
@@ -1186,6 +1194,7 @@ mod tests {
             None,
             tools,
             safety,
+            SandboxReadiness::DisabledByConfig,
         ));
 
         // Insert a due cron routine
diff --git a/tests/e2e_telegram_message_routing.rs b/tests/e2e_telegram_message_routing.rs
index a96aabe4..fe9a9b04 100644
--- a/tests/e2e_telegram_message_routing.rs
+++ b/tests/e2e_telegram_message_routing.rs
@@ -198,6 +198,7 @@ mod tests {
             http_interceptor: None,
             transcription: None,
             document_extraction: None,
+            sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
             builder: None,
         };
 
diff --git a/tests/support/gateway_workflow_harness.rs b/tests/support/gateway_workflow_harness.rs
index c2db4427..f5f01266 100644
--- a/tests/support/gateway_workflow_harness.rs
+++ b/tests/support/gateway_workflow_harness.rs
@@ -257,6 +257,7 @@ impl GatewayWorkflowHarness {
                 http_interceptor: None,
                 transcription: None,
                 document_extraction: None,
+                sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
                 builder: None,
             },
             channels,
diff --git a/tests/support/test_rig.rs b/tests/support/test_rig.rs
index e6c4a6e2..d078dc77 100644
--- a/tests/support/test_rig.rs
+++ b/tests/support/test_rig.rs
@@ -578,6 +578,7 @@ impl TestRigBuilder {
                     None,
                     components.tools.clone(),
                     components.safety.clone(),
+                    ironclaw::agent::SandboxReadiness::Available, // tests don't use real Docker
                 ));
                 components
                     .tools
@@ -642,6 +643,7 @@ impl TestRigBuilder {
             },
             transcription: None,
             document_extraction: None,
+            sandbox_readiness: ironclaw::agent::SandboxReadiness::Available, // tests don't use real Docker
             builder: None,
         };