diff --git a/app/src/providers/ChatRuntimeProvider.tsx b/app/src/providers/ChatRuntimeProvider.tsx
index 8c9167ac4..b9a5c304e 100644
--- a/app/src/providers/ChatRuntimeProvider.tsx
+++ b/app/src/providers/ChatRuntimeProvider.tsx
@@ -42,6 +42,8 @@ import { IS_PROD } from '../utils/config';
 import { formatTimelineEntry, promptFromArgsBuffer } from '../utils/toolTimelineFormatting';
 
 const logChatRuntime = debug('openhuman:chat-runtime');
+const USER_FACING_AGENT_ERROR_MESSAGE =
+  'Something went wrong. Please try again.\nThis error has been reported. You can also report it on Discord.\n<openhuman-link path="community/discord">Report on Discord</openhuman-link>';
 
 type SegmentDelivery = { segments: Map<number, string> };
 
@@ -781,14 +783,11 @@ const ChatRuntimeProvider = ({ children }: { children: React.ReactNode }) => {
           const threadMessages = currentState.thread.messagesByThreadId[event.thread_id] ?? [];
           const lastMsg = threadMessages[threadMessages.length - 1];
           if (
-            !(
-              lastMsg?.sender === 'agent' &&
-              lastMsg?.content === 'Something went wrong — please try again.'
-            )
+            !(lastMsg?.sender === 'agent' && lastMsg?.content === USER_FACING_AGENT_ERROR_MESSAGE)
           ) {
             void dispatch(
               addInferenceResponse({
-                content: 'Something went wrong — please try again.',
+                content: USER_FACING_AGENT_ERROR_MESSAGE,
                 threadId: event.thread_id,
               })
             );
diff --git a/app/src/providers/__tests__/ChatRuntimeProvider.test.tsx b/app/src/providers/__tests__/ChatRuntimeProvider.test.tsx
index 90cba448d..31a0a04f2 100644
--- a/app/src/providers/__tests__/ChatRuntimeProvider.test.tsx
+++ b/app/src/providers/__tests__/ChatRuntimeProvider.test.tsx
@@ -436,6 +436,90 @@ describe('ChatRuntimeProvider — dedupe, proactive resolution, mid-turn invaria
       expect(timeline[0]?.status).toBe('error');
       expect(store.getState().chatRuntime.inferenceStatusByThread['t-err']).toBeUndefined();
     });
+
+    it('adds a sanitized user-facing error bubble with Discord report action on chat_error', async () => {
+      const listeners = renderProvider();
+
+      act(() => {
+        listeners.onError?.({
+          thread_id: 't-err-sanitized',
+          request_id: 'r1',
+          message:
+            'agent job failed: error sending request for url (https://staging-api.alphahuman.xyz/openai/v1/chat/completions)',
+          error_type: 'inference',
+          round: 0,
+        });
+      });
+
+      await waitFor(() =>
+        expect(threadApi.appendMessage).toHaveBeenCalledWith(
+          't-err-sanitized',
+          expect.objectContaining({
+            sender: 'agent',
+            content: expect.stringContaining('Something went wrong. Please try again.'),
+          })
+        )
+      );
+      expect(threadApi.appendMessage).toHaveBeenCalledWith(
+        't-err-sanitized',
+        expect.objectContaining({
+          content: expect.stringContaining(
+            '<openhuman-link path="community/discord">Report on Discord</openhuman-link>'
+          ),
+        })
+      );
+      expect(threadApi.appendMessage).not.toHaveBeenCalledWith(
+        't-err-sanitized',
+        expect.objectContaining({
+          content: expect.stringContaining('https://staging-api.alphahuman.xyz'),
+        })
+      );
+    });
+
+    it('does not append duplicate fallback error bubble when the previous message already matches', async () => {
+      const listeners = renderProvider();
+
+      act(() => {
+        listeners.onError?.({
+          thread_id: 't-err-dedupe',
+          request_id: 'r1',
+          message: 'transport fail one',
+          error_type: 'inference',
+          round: 0,
+        });
+      });
+
+      await waitFor(() =>
+        expect(threadApi.appendMessage).toHaveBeenCalledWith(
+          't-err-dedupe',
+          expect.objectContaining({
+            content: expect.stringContaining('Something went wrong. Please try again.'),
+          })
+        )
+      );
+
+      act(() => {
+        listeners.onError?.({
+          thread_id: 't-err-dedupe',
+          request_id: 'r2',
+          message: 'transport fail two',
+          error_type: 'inference',
+          round: 0,
+        });
+      });
+
+      await waitFor(() => {
+        const matchingCalls = vi
+          .mocked(threadApi.appendMessage)
+          .mock.calls.filter(
+            call =>
+              call[0] === 't-err-dedupe' &&
+              typeof call[1]?.content === 'string' &&
+              call[1].content.includes('Something went wrong. Please try again.')
+          );
+        expect(matchingCalls).toHaveLength(1);
+      });
+    });
   });
 
   // Live subagent activity (#1122) — the parent thread surfaces a
diff --git a/src/openhuman/channels/providers/web.rs b/src/openhuman/channels/providers/web.rs
index 0e7c0ea11..10c0e2086 100644
--- a/src/openhuman/channels/providers/web.rs
+++ b/src/openhuman/channels/providers/web.rs
@@ -86,6 +86,9 @@ static THREAD_SESSIONS: Lazy<Mutex<HashMap<String, SessionEntry>>> =
 
 static IN_FLIGHT: Lazy<Mutex<HashMap<String, InFlightEntry>>> =
     Lazy::new(|| Mutex::new(HashMap::new()));
+#[cfg(test)]
+static TEST_FORCED_RUN_CHAT_TASK_ERROR: Lazy<Mutex<Option<String>>> =
+    Lazy::new(|| Mutex::new(None));
 static BUDGET_ERROR_NORMALIZE_RE: Lazy<Regex> =
     Lazy::new(|| Regex::new(r"[-_\s]+").expect("budget normalize regex"));
 static BUDGET_ERROR_PATTERNS: Lazy<Vec<Regex>> = Lazy::new(|| {
@@ -123,6 +126,10 @@ fn inference_budget_exceeded_user_message() -> &'static str {
     "I don't have any budget available right now. Please top up your credits or choose a plan to continue."
 }
 
+fn generic_inference_error_user_message() -> &'static str {
+    "Something went wrong. Please try again.\nThis error has been reported. You can also report it on Discord.\n<openhuman-link path=\"community/discord\">Report on Discord</openhuman-link>"
+}
+
 fn prompt_guard_user_message(action: PromptEnforcementAction) -> &'static str {
     match action {
         PromptEnforcementAction::Allow => "Message accepted.",
@@ -135,6 +142,12 @@ fn prompt_guard_user_message(action: PromptEnforcementAction) -> &'static str {
     }
 }
 
+#[cfg(test)]
+pub(super) async fn set_test_forced_run_chat_task_error(message: Option<&str>) {
+    let mut slot = TEST_FORCED_RUN_CHAT_TASK_ERROR.lock().await;
+    *slot = message.map(str::to_string);
+}
+
 pub async fn start_chat(
     client_id: &str,
     thread_id: &str,
@@ -263,13 +276,28 @@ pub async fn start_chat(
                     request_id_task,
                     err
                 );
+                let detailed = format!(
+                    "run_chat_task failed client_id={} thread_id={} request_id={} error={}",
+                    client_id_task, thread_id_task, request_id_task, err
+                );
+                crate::core::observability::report_error(
+                    detailed.as_str(),
+                    "web_channel",
+                    "run_chat_task",
+                    &[
+                        ("channel", "web"),
+                        ("error_type", "inference"),
+                        ("thread_id", thread_id_task.as_str()),
+                        ("request_id", request_id_task.as_str()),
+                    ],
+                );
                 publish_web_channel_event(WebChannelEvent {
                     event: "chat_error".to_string(),
                     client_id: client_id_task.clone(),
                     thread_id: thread_id_task.clone(),
                     request_id: request_id_task.clone(),
                     full_response: None,
-                    message: Some(err),
+                    message: Some(generic_inference_error_user_message().to_string()),
                     error_type: Some("inference".to_string()),
                     tool_name: None,
                     skill_id: None,
@@ -392,6 +420,20 @@ async fn run_chat_task(
     model_override: Option<String>,
     temperature: Option<f64>,
 ) -> Result<WebChatTaskResult, String> {
+    #[cfg(test)]
+    {
+        let mut slot = TEST_FORCED_RUN_CHAT_TASK_ERROR.lock().await;
+        if let Some(forced) = slot.take() {
+            log::debug!(
+                "[web-channel][test] forced run_chat_task failure client_id={} thread_id={} request_id={}",
+                client_id,
+                thread_id,
+                request_id
+            );
+            return Err(forced);
+        }
+    }
+
     let config = config_rpc::load_config_with_timeout().await?;
     let map_key = key_for(client_id, thread_id);
     let model_override = normalize_model_override(model_override);
diff --git a/src/openhuman/channels/providers/web_tests.rs b/src/openhuman/channels/providers/web_tests.rs
index 23b88b4a7..128aad9ac 100644
--- a/src/openhuman/channels/providers/web_tests.rs
+++ b/src/openhuman/channels/providers/web_tests.rs
@@ -1,11 +1,24 @@
 use super::{
     all_web_channel_controller_schemas, all_web_channel_registered_controllers, cancel_chat,
-    event_session_id_for, inference_budget_exceeded_user_message,
-    is_inference_budget_exceeded_error, json_output, key_for, normalize_model_override,
-    optional_f64, optional_string, required_string, schemas, start_chat,
-    subscribe_web_channel_events,
+    event_session_id_for, generic_inference_error_user_message,
+    inference_budget_exceeded_user_message, is_inference_budget_exceeded_error, json_output,
+    key_for, normalize_model_override, optional_f64, optional_string, required_string, schemas,
+    set_test_forced_run_chat_task_error, start_chat, subscribe_web_channel_events,
 };
 use crate::core::TypeSchema;
+use tokio::time::{timeout, Duration};
+
+/// Ensures the test-only forced run_chat_task failure toggle is always reset,
+/// even if the test panics before reaching explicit cleanup code.
+struct TestForcedRunChatTaskErrorGuard;
+
+impl Drop for TestForcedRunChatTaskErrorGuard {
+    fn drop(&mut self) {
+        tokio::spawn(async {
+            set_test_forced_run_chat_task_error(None).await;
+        });
+    }
+}
 
 #[tokio::test]
 async fn start_chat_validates_required_fields() {
@@ -58,6 +71,49 @@ async fn cancel_chat_validates_required_fields() {
     assert!(err.contains("thread_id is required"));
 }
 
+#[tokio::test]
+async fn start_chat_emits_sanitized_chat_error_on_inference_failure() {
+    set_test_forced_run_chat_task_error(Some(
+        "error sending request for url (https://internal-api.example.invalid/openai/v1/chat/completions)",
+    ))
+    .await;
+    let _forced_error_guard = TestForcedRunChatTaskErrorGuard;
+
+    let mut rx = subscribe_web_channel_events();
+    let request_id = start_chat(
+        "coverage-client",
+        "coverage-thread",
+        "Please summarize this in one line.",
+        None,
+        None,
+    )
+    .await
+    .expect("start_chat should accept valid request");
+
+    let expected = generic_inference_error_user_message().to_string();
+    let recv = timeout(Duration::from_secs(20), async move {
+        loop {
+            let event = rx.recv().await.expect("event stream should stay open");
+            if event.event != "chat_error" {
+                continue;
+            }
+            if event.request_id != request_id {
+                continue;
+            }
+            return event;
+        }
+    })
+    .await
+    .expect("expected chat_error event for started chat request");
+
+    let message = recv.message.unwrap_or_default();
+    assert_eq!(message, expected);
+    assert!(
+        !message.contains("error sending request for url"),
+        "chat error payload must not expose raw transport details"
+    );
+}
+
 #[test]
 fn detects_backend_budget_exhaustion_error() {
     assert!(is_inference_budget_exceeded_error(
@@ -78,6 +134,15 @@ fn budget_exceeded_copy_mentions_top_up() {
     assert!(message.contains("credits"));
 }
 
+#[test]
+fn generic_error_copy_is_sanitized_and_has_discord_report_action() {
+    let message = generic_inference_error_user_message();
+    assert!(message.contains("Something went wrong. Please try again."));
+    assert!(message.contains("This error has been reported."));
+    assert!(message
+        .contains("<openhuman-link path=\"community/discord\">Report on Discord</openhuman-link>"));
+}
+
 // ── Schema catalog ────────────────────────────────────────────
 
 #[test]
diff --git a/src/openhuman/cron/scheduler.rs b/src/openhuman/cron/scheduler.rs
index e1f043592..48c8b7ddf 100644
--- a/src/openhuman/cron/scheduler.rs
+++ b/src/openhuman/cron/scheduler.rs
@@ -15,6 +15,14 @@ use tokio::time::{self, Duration};
 
 const MIN_POLL_SECONDS: u64 = 5;
 const SHELL_JOB_TIMEOUT_SECS: u64 = 120;
+const AGENT_JOB_USER_FAILURE_MESSAGE: &str = "Something went wrong. Please try again.\nThis error has been reported. You can also report it on Discord.\n<openhuman-link path=\"community/discord\">Report on Discord</openhuman-link>";
+
+fn agent_session_target_tag(target: &SessionTarget) -> &'static str {
+    match target {
+        SessionTarget::Main => "main",
+        SessionTarget::Isolated => "isolated",
+    }
+}
 
 pub async fn run(config: Config) -> Result<()> {
     // Ensure the global event bus is initialized so cron delivery events
@@ -77,15 +85,22 @@ async fn execute_job_with_retry(
     job: &CronJob,
 ) -> (bool, String) {
     let mut last_output = String::new();
+    let mut last_agent_error: Option<String> = None;
     let retries = config.reliability.scheduler_retries;
     let mut backoff_ms = config.reliability.provider_backoff_ms.max(200);
 
     for attempt in 0..=retries {
-        let (success, output) = match job.job_type {
-            JobType::Shell => run_job_command(config, security, job).await,
+        let (success, output, agent_error) = match job.job_type {
+            JobType::Shell => {
+                let (success, output) = run_job_command(config, security, job).await;
+                (success, output, None)
+            }
             JobType::Agent => run_agent_job(config, job).await,
         };
         last_output = output;
+        if agent_error.is_some() {
+            last_agent_error = agent_error;
+        }
 
         if success {
             return (true, last_output);
@@ -103,6 +118,26 @@ async fn execute_job_with_retry(
         }
     }
 
+    if matches!(job.job_type, JobType::Agent) {
+        let report_message = last_agent_error
+            .as_deref()
+            .unwrap_or_else(|| last_output.as_str());
+        crate::core::observability::report_error(
+            report_message,
+            "cron",
+            "agent_job",
+            &[
+                ("job_id", job.id.as_str()),
+                ("agent_id", job.agent_id.as_deref().unwrap_or("none")),
+                (
+                    "session_target",
+                    agent_session_target_tag(&job.session_target),
+                ),
+                ("failure", "retries_exhausted"),
+            ],
+        );
+    }
+
     (false, last_output)
 }
 
@@ -170,7 +205,7 @@ async fn execute_and_persist_job(
     (job.id.clone(), success, failure_message)
 }
 
-async fn run_agent_job(config: &Config, job: &CronJob) -> (bool, String) {
+async fn run_agent_job(config: &Config, job: &CronJob) -> (bool, String, Option<String>) {
     use crate::openhuman::agent::Agent;
 
     let name = job.name.clone().unwrap_or_else(|| "cron-job".to_string());
@@ -249,8 +284,13 @@ async fn run_agent_job(config: &Config, job: &CronJob) -> (bool, String) {
             } else {
                 response
             },
+            None,
+        ),
+        Err(e) => (
+            false,
+            AGENT_JOB_USER_FAILURE_MESSAGE.to_string(),
+            Some(e.to_string()),
         ),
-        Err(e) => (false, format!("agent job failed: {e}")),
     }
 }
 
diff --git a/src/openhuman/cron/scheduler_tests.rs b/src/openhuman/cron/scheduler_tests.rs
index b20efba80..c89b79678 100644
--- a/src/openhuman/cron/scheduler_tests.rs
+++ b/src/openhuman/cron/scheduler_tests.rs
@@ -45,6 +45,22 @@ fn test_job(command: &str) -> CronJob {
     }
 }
 
+#[test]
+fn agent_failure_copy_mentions_retry_reporting_and_discord() {
+    assert!(AGENT_JOB_USER_FAILURE_MESSAGE.contains("Something went wrong. Please try again."));
+    assert!(AGENT_JOB_USER_FAILURE_MESSAGE.contains("This error has been reported."));
+    assert!(AGENT_JOB_USER_FAILURE_MESSAGE.contains("Report on Discord"));
+}
+
+#[test]
+fn agent_session_target_tag_matches_expected_values() {
+    assert_eq!(agent_session_target_tag(&SessionTarget::Main), "main");
+    assert_eq!(
+        agent_session_target_tag(&SessionTarget::Isolated),
+        "isolated"
+    );
+}
+
 #[cfg(not(windows))]
 #[tokio::test]
 async fn run_job_command_success() {
@@ -203,11 +219,20 @@ async fn run_agent_job_returns_error_without_provider_key() {
     job.job_type = JobType::Agent;
     job.prompt = Some("Say hello".into());
 
-    let (success, output) = run_agent_job(&config, &job).await;
+    let (success, output, raw_error) = run_agent_job(&config, &job).await;
     assert!(!success, "Agent job without provider key should fail");
+    assert!(output.contains("Something went wrong. Please try again."));
+    assert!(output.contains("This error has been reported."));
+    assert!(output.contains("Report on Discord"));
     assert!(
-        !output.is_empty(),
-        "Expected non-empty error output from failed agent job"
+        raw_error
+            .as_deref()
+            .is_some_and(|value| !value.trim().is_empty()),
+        "Expected raw agent error for observability after retries are exhausted"
+    );
+    assert!(
+        !output.contains("error sending request for url"),
+        "Expected sanitized output without raw transport details"
     );
 }