diff --git a/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts b/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
index 35fc741db58..47460c5efa7 100644
--- a/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
+++ b/src/agents/pi-embedded-helpers.formatassistanterrortext.test.ts
@@ -125,6 +125,27 @@ describe("formatAssistantErrorText", () => {
     const msg = makeAssistantError("request ended without sending any chunks");
     expect(formatAssistantErrorText(msg)).toBe("LLM request timed out.");
   });
+
+  it("returns a connection-refused message for ECONNREFUSED failures", () => {
+    const msg = makeAssistantError("connect ECONNREFUSED 127.0.0.1:443 during upstream call");
+    expect(formatAssistantErrorText(msg)).toBe(
+      "LLM request failed: connection refused by the provider endpoint.",
+    );
+  });
+
+  it("returns a DNS-specific message for provider lookup failures", () => {
+    const msg = makeAssistantError("dial tcp: lookup api.example.com: no such host (ENOTFOUND)");
+    expect(formatAssistantErrorText(msg)).toBe(
+      "LLM request failed: DNS lookup for the provider endpoint failed.",
+    );
+  });
+
+  it("returns an interrupted-connection message for socket hang ups", () => {
+    const msg = makeAssistantError("socket hang up");
+    expect(formatAssistantErrorText(msg)).toBe(
+      "LLM request failed: network connection was interrupted.",
+    );
+  });
 });
 
 describe("formatRawAssistantErrorForUi", () => {
diff --git a/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts b/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
index 2808d320cc5..82fe67c47f4 100644
--- a/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
+++ b/src/agents/pi-embedded-helpers.sanitizeuserfacingtext.test.ts
@@ -88,6 +88,14 @@ describe("sanitizeUserFacingText", () => {
     );
   });
 
+  it("returns a transport-specific message for prefixed ECONNREFUSED errors", () => {
+    expect(
+      sanitizeUserFacingText("Error: connect ECONNREFUSED 127.0.0.1:443", {
+        errorContext: true,
+      }),
+    ).toBe("LLM request failed: connection refused by the provider endpoint.");
+  });
+
   it.each([
     {
       input: "Hello there!\n\nHello there!",
diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index 7719ecb41a0..bb3d6b78206 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -65,6 +65,57 @@ function formatRateLimitOrOverloadedErrorCopy(raw: string): string | undefined {
   return undefined;
 }
 
+function formatTransportErrorCopy(raw: string): string | undefined {
+  if (!raw) {
+    return undefined;
+  }
+  const lower = raw.toLowerCase();
+
+  if (
+    /\beconnrefused\b/i.test(raw) ||
+    lower.includes("connection refused") ||
+    lower.includes("actively refused")
+  ) {
+    return "LLM request failed: connection refused by the provider endpoint.";
+  }
+
+  if (
+    /\beconnreset\b|\beconnaborted\b|\benetreset\b|\bepipe\b/i.test(raw) ||
+    lower.includes("socket hang up") ||
+    lower.includes("connection reset") ||
+    lower.includes("connection aborted")
+  ) {
+    return "LLM request failed: network connection was interrupted.";
+  }
+
+  if (
+    /\benotfound\b|\beai_again\b/i.test(raw) ||
+    lower.includes("getaddrinfo") ||
+    lower.includes("no such host") ||
+    lower.includes("dns")
+  ) {
+    return "LLM request failed: DNS lookup for the provider endpoint failed.";
+  }
+
+  if (
+    /\benetunreach\b|\behostunreach\b|\behostdown\b/i.test(raw) ||
+    lower.includes("network is unreachable") ||
+    lower.includes("host is unreachable")
+  ) {
+    return "LLM request failed: the provider endpoint is unreachable from this host.";
+  }
+
+  if (
+    lower.includes("fetch failed") ||
+    lower.includes("connection error") ||
+    lower.includes("network request failed")
+  ) {
+    return "LLM request failed: network connection error.";
+  }
+
+  return undefined;
+}
+
 function isReasoningConstraintErrorMessage(raw: string): boolean {
   if (!raw) {
     return false;
@@ -566,6 +617,11 @@ export function formatAssistantErrorText(
     return transientCopy;
   }
 
+  const transportCopy = formatTransportErrorCopy(raw);
+  if (transportCopy) {
+    return transportCopy;
+  }
+
   if (isTimeoutErrorMessage(raw)) {
     return "LLM request timed out.";
   }
@@ -626,6 +682,10 @@ export function sanitizeUserFacingText(text: string, opts?: { errorContext?: boo
       if (prefixedCopy) {
         return prefixedCopy;
       }
+      const transportCopy = formatTransportErrorCopy(trimmed);
+      if (transportCopy) {
+        return transportCopy;
+      }
       if (isTimeoutErrorMessage(trimmed)) {
         return "LLM request timed out.";
       }
diff --git a/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts b/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
index 911b124113a..9ffd7a53a72 100644
--- a/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
@@ -58,14 +58,16 @@ describe("handleAgentEnd", () => {
     expect(warn.mock.calls[0]?.[1]).toMatchObject({
       event: "embedded_run_agent_end",
       runId: "run-1",
-      error: "connection refused",
+      error: "LLM request failed: connection refused by the provider endpoint.",
       rawErrorPreview: "connection refused",
+      consoleMessage:
+        "embedded run agent end: runId=run-1 isError=true model=unknown provider=unknown error=LLM request failed: connection refused by the provider endpoint. rawError=connection refused",
     });
     expect(onAgentEvent).toHaveBeenCalledWith({
       stream: "lifecycle",
       data: {
         phase: "error",
-        error: "connection refused",
+        error: "LLM request failed: connection refused by the provider endpoint.",
       },
     });
   });
@@ -92,7 +94,7 @@ describe("handleAgentEnd", () => {
       failoverReason: "overloaded",
       providerErrorType: "overloaded_error",
       consoleMessage:
-        "embedded run agent end: runId=run-1 isError=true model=claude-test provider=anthropic error=The AI service is temporarily overloaded. Please try again in a moment.",
+        'embedded run agent end: runId=run-1 isError=true model=claude-test provider=anthropic error=The AI service is temporarily overloaded. Please try again in a moment. rawError={"type":"error","error":{"type":"overloaded_error","message":"Overloaded"}}',
     });
   });
 
@@ -112,7 +114,7 @@ describe("handleAgentEnd", () => {
     const meta = warn.mock.calls[0]?.[1];
     expect(meta).toMatchObject({
       consoleMessage:
-        "embedded run agent end: runId=run-1 isError=true model=claude sonnet 4 provider=anthropic]8;;https://evil.test error=connection refused",
+        "embedded run agent end: runId=run-1 isError=true model=claude sonnet 4 provider=anthropic]8;;https://evil.test error=LLM request failed: connection refused by the provider endpoint. rawError=connection refused",
     });
     expect(meta?.consoleMessage).not.toContain("\n");
     expect(meta?.consoleMessage).not.toContain("\r");
diff --git a/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts b/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
index 973de1ebefc..7edc299460c 100644
--- a/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
@@ -50,6 +50,8 @@ export function handleAgentEnd(ctx: EmbeddedPiSubscribeContext) {
     const safeRunId = sanitizeForConsole(ctx.params.runId) ?? "-";
     const safeModel = sanitizeForConsole(lastAssistant.model) ?? "unknown";
     const safeProvider = sanitizeForConsole(lastAssistant.provider) ?? "unknown";
+    const safeRawErrorPreview = sanitizeForConsole(observedError.rawErrorPreview);
+    const rawErrorConsoleSuffix = safeRawErrorPreview ? ` rawError=${safeRawErrorPreview}` : "";
     ctx.log.warn("embedded run agent end", {
       event: "embedded_run_agent_end",
       tags: ["error_handling", "lifecycle", "agent_end", "assistant_error"],
@@ -60,7 +62,7 @@ export function handleAgentEnd(ctx: EmbeddedPiSubscribeContext) {
       model: lastAssistant.model,
       provider: lastAssistant.provider,
       ...observedError,
-      consoleMessage: `embedded run agent end: runId=${safeRunId} isError=true model=${safeModel} provider=${safeProvider} error=${safeErrorText}`,
+      consoleMessage: `embedded run agent end: runId=${safeRunId} isError=true model=${safeModel} provider=${safeProvider} error=${safeErrorText}${rawErrorConsoleSuffix}`,
     });
     emitAgentEvent({
       runId: ctx.params.runId,