diff --git a/ui/src/styles/chat/grouped.css b/ui/src/styles/chat/grouped.css
index 39b641826..237fdb24a 100644
--- a/ui/src/styles/chat/grouped.css
+++ b/ui/src/styles/chat/grouped.css
@@ -18,6 +18,21 @@
   justify-content: flex-start;
 }
 
+.chat-group.system {
+  justify-content: center;
+  margin-left: 0;
+  margin-right: 0;
+}
+
+.chat-group.system .chat-group-messages {
+  align-items: center;
+  max-width: min(820px, 90%);
+}
+
+.chat-group.system .chat-group-footer {
+  justify-content: center;
+}
+
 .chat-group-messages {
   display: flex;
   flex-direction: column;
@@ -89,6 +104,10 @@
   color: var(--muted);
 }
 
+.chat-group.system .chat-avatar {
+  display: none;
+}
+
 /* Image avatar support */
 img.chat-avatar {
   display: block;
@@ -228,6 +247,21 @@ img.chat-avatar {
   border-color: transparent;
 }
 
+.chat-group.system .chat-bubble {
+  background: var(--bg-muted);
+  border-color: var(--border);
+  color: var(--muted);
+  font-size: 12px;
+  line-height: 1.4;
+  padding: 8px 12px;
+  text-align: center;
+}
+
+:root[data-theme="light"] .chat-group.system .chat-bubble {
+  background: rgba(148, 163, 184, 0.12);
+  border-color: rgba(148, 163, 184, 0.35);
+}
+
 :root[data-theme="light"] .chat-group.user .chat-bubble {
   border-color: rgba(234, 88, 12, 0.2);
   background: rgba(251, 146, 60, 0.12);
diff --git a/ui/src/ui/chat/grouped-render.ts b/ui/src/ui/chat/grouped-render.ts
index 4a9ccec14..77bff47f2 100644
--- a/ui/src/ui/chat/grouped-render.ts
+++ b/ui/src/ui/chat/grouped-render.ts
@@ -120,12 +120,16 @@ export function renderMessageGroup(
       ? "You"
       : normalizedRole === "assistant"
         ? assistantName
+        : normalizedRole === "system"
+          ? "System"
         : normalizedRole;
   const roleClass =
     normalizedRole === "user"
       ? "user"
       : normalizedRole === "assistant"
         ? "assistant"
+        : normalizedRole === "system"
+          ? "system"
         : "other";
   const timestamp = new Date(group.timestamp).toLocaleTimeString([], {
     hour: "numeric",
@@ -171,6 +175,8 @@ function renderAvatar(
       ? "U"
       : normalized === "assistant"
         ? assistantName.charAt(0).toUpperCase() || "A"
+        : normalized === "system"
+          ? "!"
         : normalized === "tool"
           ? "⚙"
           : "?";
@@ -179,6 +185,8 @@ function renderAvatar(
       ? "user"
       : normalized === "assistant"
         ? "assistant"
+      : normalized === "system"
+          ? "system"
       : normalized === "tool"
           ? "tool"
           : "other";
diff --git a/ui/src/ui/chat/message-normalizer.test.ts b/ui/src/ui/chat/message-normalizer.test.ts
index 132a4be17..151898efb 100644
--- a/ui/src/ui/chat/message-normalizer.test.ts
+++ b/ui/src/ui/chat/message-normalizer.test.ts
@@ -3,6 +3,7 @@ import {
   normalizeMessage,
   normalizeRoleForGrouping,
   isToolResultMessage,
+  splitSystemPreface,
 } from "./message-normalizer";
 
 describe("message-normalizer", () => {
@@ -138,6 +139,48 @@ describe("message-normalizer", () => {
     });
   });
 
+  describe("splitSystemPreface", () => {
+    it("splits leading system block into system message", () => {
+      const normalized = normalizeMessage({
+        role: "user",
+        content: "System: [2026-01-26 10:00:00 UTC] Exec finished\n\nRun complete",
+        timestamp: 123,
+      });
+      const result = splitSystemPreface(normalized);
+      expect(result.systemMessage?.role).toBe("system");
+      expect(result.systemMessage?.content).toEqual([
+        { type: "text", text: expect.stringContaining("Exec finished") },
+      ]);
+      expect(result.message.content).toEqual([
+        { type: "text", text: "Run complete" },
+      ]);
+    });
+
+    it("keeps user message when no system prefix", () => {
+      const normalized = normalizeMessage({
+        role: "user",
+        content: "Hello",
+        timestamp: 123,
+      });
+      const result = splitSystemPreface(normalized);
+      expect(result.systemMessage).toBeNull();
+      expect(result.message.content).toEqual([{ type: "text", text: "Hello" }]);
+    });
+
+    it("creates system message even when remainder is empty", () => {
+      const normalized = normalizeMessage({
+        role: "user",
+        content: "System: [2026-01-26 10:00:00 UTC] Gateway restart",
+        timestamp: 123,
+      });
+      const result = splitSystemPreface(normalized);
+      expect(result.systemMessage?.content).toEqual([
+        { type: "text", text: expect.stringContaining("Gateway restart") },
+      ]);
+      expect(result.message.content).toEqual([]);
+    });
+  });
+
   describe("isToolResultMessage", () => {
     it("returns true for toolresult role", () => {
       expect(isToolResultMessage({ role: "toolresult" })).toBe(true);
diff --git a/ui/src/ui/chat/message-normalizer.ts b/ui/src/ui/chat/message-normalizer.ts
index e4cbab81d..c3b57fdeb 100644
--- a/ui/src/ui/chat/message-normalizer.ts
+++ b/ui/src/ui/chat/message-normalizer.ts
@@ -59,6 +59,74 @@ export function normalizeMessage(message: unknown): NormalizedMessage {
   return { role, content, timestamp, id };
 }
 
+type SplitSystemMessageResult = {
+  systemMessage: NormalizedMessage | null;
+  message: NormalizedMessage;
+};
+
+const SYSTEM_LINE_PREFIX = "System: ";
+
+function parseSystemLine(line: string): string | null {
+  const trimmed = line.trim();
+  if (!trimmed.startsWith(SYSTEM_LINE_PREFIX)) return null;
+  const payload = trimmed.slice(SYSTEM_LINE_PREFIX.length).trim();
+  return payload ? payload : null;
+}
+
+export function splitSystemPreface(
+  message: NormalizedMessage,
+): SplitSystemMessageResult {
+  if (message.role.toLowerCase() !== "user") {
+    return { systemMessage: null, message };
+  }
+
+  const textParts = message.content
+    .filter((item) => item.type === "text" && typeof item.text === "string")
+    .map((item) => item.text ?? "")
+    .filter((text) => text.trim().length > 0);
+
+  if (textParts.length === 0) return { systemMessage: null, message };
+
+  const joined = textParts.join("\n").trim();
+  if (!joined.startsWith(SYSTEM_LINE_PREFIX)) {
+    return { systemMessage: null, message };
+  }
+
+  const lines = joined.split(/\r?\n/);
+  const systemLines: string[] = [];
+  let idx = 0;
+  while (idx < lines.length) {
+    const parsed = parseSystemLine(lines[idx] ?? "");
+    if (!parsed) break;
+    systemLines.push(parsed);
+    idx += 1;
+  }
+
+  if (systemLines.length === 0) return { systemMessage: null, message };
+
+  // Skip blank separator line after system block, if present.
+  while (idx < lines.length && !lines[idx]?.trim()) idx += 1;
+  const remainder = lines.slice(idx).join("\n").trim();
+
+  const systemMessage: NormalizedMessage = {
+    role: "system",
+    content: [{ type: "text", text: systemLines.join("\n") }],
+    timestamp: message.timestamp,
+  };
+
+  if (!remainder) {
+    return { systemMessage, message: { ...message, content: [] } };
+  }
+
+  return {
+    systemMessage,
+    message: {
+      ...message,
+      content: [{ type: "text", text: remainder }],
+    },
+  };
+}
+
 /**
  * Normalize role for grouping purposes.
  */
diff --git a/ui/src/ui/views/chat.ts b/ui/src/ui/views/chat.ts
index f5fb6e80b..65de8e4b6 100644
--- a/ui/src/ui/views/chat.ts
+++ b/ui/src/ui/views/chat.ts
@@ -8,6 +8,7 @@ import { icons } from "../icons";
 import {
   normalizeMessage,
   normalizeRoleForGrouping,
+  splitSystemPreface,
 } from "../chat/message-normalizer";
 import {
   renderMessageGroup,
@@ -438,10 +439,23 @@ function buildChatItems(props: ChatProps): Array<ChatItem | MessageGroup> {
       continue;
     }
 
+    const split = splitSystemPreface(normalized);
+    if (split.systemMessage) {
+      items.push({
+        kind: "message",
+        key: `system:${messageKey(msg, i)}`,
+        message: split.systemMessage,
+      });
+    }
+
+    if (split.systemMessage && split.message.content.length === 0) {
+      continue;
+    }
+
     items.push({
       kind: "message",
       key: messageKey(msg, i),
-      message: msg,
+      message: split.systemMessage ? split.message : msg,
     });
   }
   if (props.showThinking) {