diff --git a/CHANGELOG.md b/CHANGELOG.md
index e094f9184..8c8da5374 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ Docs: https://docs.clawd.bot
 - Repo: remove the Peekaboo git submodule now that the SPM release is used.
 - Plugins: require manifest-embedded config schemas, validate configs without loading plugin code, and surface plugin config warnings. (#1272) — thanks @thewilloftheshadow.
 - Plugins: move channel catalog metadata into plugin manifests; align Nextcloud Talk policy helpers with core patterns. (#1290) — thanks @NicholaiVogel.
+- UI: separate tool output from assistant reasoning and add a thinking toggle. (#1292) — thanks @bradleypriest.
 ### Fixes
 - Web search: infer Perplexity base URL from API key source (direct vs OpenRouter).
 - TUI: keep thinking blocks ordered before content during streaming and isolate per-run assembly. (#1202) — thanks @aaronveklabs.
diff --git a/ui/src/ui/chat/grouped-render.ts b/ui/src/ui/chat/grouped-render.ts
index e84d2b7f1..3b0f75c16 100644
--- a/ui/src/ui/chat/grouped-render.ts
+++ b/ui/src/ui/chat/grouped-render.ts
@@ -3,7 +3,7 @@ import { unsafeHTML } from "lit/directives/unsafe-html.js";
 
 import { toSanitizedMarkdownHtml } from "../markdown";
 import type { MessageGroup } from "../types/chat-types";
-import { isToolResultMessage, normalizeRoleForGrouping } from "./message-normalizer";
+import { classifyMessage } from "./message-classifier";
 import {
   extractText,
   extractThinking,
@@ -62,19 +62,25 @@ export function renderMessageGroup(
   group: MessageGroup,
   opts: { onOpenSidebar?: (content: string) => void; showReasoning: boolean },
 ) {
-  const normalizedRole = normalizeRoleForGrouping(group.role);
+  const roleKind = group.role;
   const who =
-    normalizedRole === "user"
+    roleKind === "user"
       ? "You"
-      : normalizedRole === "assistant"
+      : roleKind === "assistant"
         ? "Assistant"
-        : normalizedRole;
+        : roleKind === "tool"
+          ? "Tool"
+          : roleKind === "system"
+            ? "System"
+            : roleKind;
   const roleClass =
-    normalizedRole === "user"
+    roleKind === "user"
       ? "user"
-      : normalizedRole === "assistant"
+      : roleKind === "assistant"
         ? "assistant"
-        : "other";
+        : roleKind === "tool"
+          ? "tool"
+          : "other";
   const timestamp = new Date(group.timestamp).toLocaleTimeString([], {
     hour: "numeric",
     minute: "2-digit",
@@ -82,7 +88,7 @@ export function renderMessageGroup(
 
   return html`
     <div class="chat-group ${roleClass}">
-      ${renderAvatar(group.role)}
+      ${renderAvatar(roleKind)}
       <div class="chat-group-messages">
         ${group.messages.map((item, index) =>
           renderGroupedMessage(
@@ -105,21 +111,14 @@ export function renderMessageGroup(
 }
 
 function renderAvatar(role: string) {
-  const normalized = normalizeRoleForGrouping(role);
   const initial =
-    normalized === "user"
-      ? "U"
-      : normalized === "assistant"
-        ? "A"
-        : normalized === "tool"
-          ? "⚙"
-          : "?";
+    role === "user" ? "U" : role === "assistant" ? "A" : role === "tool" ? "⚙" : "?";
   const className =
-    normalized === "user"
+    role === "user"
       ? "user"
-      : normalized === "assistant"
+      : role === "assistant"
         ? "assistant"
-        : normalized === "tool"
+        : role === "tool"
           ? "tool"
           : "other";
   return html`<div class="chat-avatar ${className}">${initial}</div>`;
@@ -130,21 +129,22 @@ function renderGroupedMessage(
   opts: { isStreaming: boolean; showReasoning: boolean },
   onOpenSidebar?: (content: string) => void,
 ) {
-  const m = message as Record<string, unknown>;
-  const role = typeof m.role === "string" ? m.role : "unknown";
+  const classification = classifyMessage(message);
+  const roleLower = classification.roleRaw.toLowerCase();
   const isToolResult =
-    isToolResultMessage(message) ||
-    role.toLowerCase() === "toolresult" ||
-    role.toLowerCase() === "tool_result" ||
-    typeof m.toolCallId === "string" ||
-    typeof m.tool_call_id === "string";
+    classification.hasToolResults ||
+    roleLower === "toolresult" ||
+    roleLower === "tool_result" ||
+    (classification.isToolLike && !classification.hasText);
 
   const toolCards = extractToolCards(message);
   const hasToolCards = toolCards.length > 0;
 
   const extractedText = extractText(message);
   const extractedThinking =
-    opts.showReasoning && role === "assistant" ? extractThinking(message) : null;
+    opts.showReasoning && classification.roleKind === "assistant"
+      ? extractThinking(message)
+      : null;
   const markdownBase = extractedText?.trim() ? extractedText : null;
   const reasoningMarkdown = extractedThinking
     ? formatReasoningMarkdown(extractedThinking)
@@ -181,4 +181,3 @@ function renderGroupedMessage(
     </div>
   `;
 }
-
diff --git a/ui/src/ui/chat/legacy-render.ts b/ui/src/ui/chat/legacy-render.ts
index 44ef25cc5..69b4cf2ca 100644
--- a/ui/src/ui/chat/legacy-render.ts
+++ b/ui/src/ui/chat/legacy-render.ts
@@ -2,10 +2,7 @@ import { html, nothing } from "lit";
 import { unsafeHTML } from "lit/directives/unsafe-html.js";
 
 import { toSanitizedMarkdownHtml } from "../markdown";
-import {
-  isToolResultMessage,
-  normalizeRoleForGrouping,
-} from "./message-normalizer";
+import { classifyMessage } from "./message-classifier";
 import {
   extractText,
   extractThinking,
@@ -38,16 +35,19 @@ export function renderMessage(
   opts?: { streaming?: boolean; showReasoning?: boolean },
 ) {
   const m = message as Record<string, unknown>;
-  const role = typeof m.role === "string" ? m.role : "unknown";
+  const classification = classifyMessage(message);
   const toolCards = extractToolCards(message);
   const hasToolCards = toolCards.length > 0;
   const isToolResult =
-    isToolResultMessage(message) ||
-    typeof m.toolCallId === "string" ||
-    typeof m.tool_call_id === "string";
+    classification.hasToolResults ||
+    classification.roleRaw.toLowerCase() === "toolresult" ||
+    classification.roleRaw.toLowerCase() === "tool_result" ||
+    (classification.isToolLike && !classification.hasText);
   const extractedText = extractText(message);
   const extractedThinking =
-    opts?.showReasoning && role === "assistant" ? extractThinking(message) : null;
+    opts?.showReasoning && classification.roleKind === "assistant"
+      ? extractThinking(message)
+      : null;
   const contentText = typeof m.content === "string" ? m.content : null;
   const fallback = hasToolCards ? null : JSON.stringify(message, null, 2);
 
@@ -72,23 +72,25 @@ export function renderMessage(
   const timestamp =
     typeof m.timestamp === "number" ? new Date(m.timestamp).toLocaleTimeString() : "";
 
-  const normalizedRole = normalizeRoleForGrouping(role);
+  const roleKind = classification.roleKind;
   const klass =
-    normalizedRole === "assistant"
+    roleKind === "assistant"
       ? "assistant"
-      : normalizedRole === "user"
+      : roleKind === "user"
         ? "user"
-        : normalizedRole === "tool"
+        : roleKind === "tool"
           ? "tool"
           : "other";
   const who =
-    normalizedRole === "assistant"
+    roleKind === "assistant"
       ? "Assistant"
-      : normalizedRole === "user"
+      : roleKind === "user"
         ? "You"
-        : normalizedRole === "tool"
-          ? "Working"
-          : normalizedRole;
+        : roleKind === "tool"
+          ? "Tool"
+          : roleKind === "system"
+            ? "System"
+            : classification.roleRaw;
 
   const toolCallId = typeof m.toolCallId === "string" ? m.toolCallId : "";
   const toolCardBase =
@@ -126,4 +128,3 @@ export function renderMessage(
     </div>
   `;
 }
-
diff --git a/ui/src/ui/chat/message-classifier.ts b/ui/src/ui/chat/message-classifier.ts
new file mode 100644
index 000000000..945f06a57
--- /dev/null
+++ b/ui/src/ui/chat/message-classifier.ts
@@ -0,0 +1,101 @@
+import { extractRawText, extractThinking } from "./message-extract";
+
+export type RoleKind = "assistant" | "user" | "tool" | "system" | "other";
+
+export type MessageClassification = {
+  roleRaw: string;
+  roleKind: RoleKind;
+  hasText: boolean;
+  hasThinking: boolean;
+  hasToolCalls: boolean;
+  hasToolResults: boolean;
+  isToolLike: boolean;
+  displayLabel: string;
+};
+
+const TOOL_CALL_TYPES = new Set([
+  "toolcall",
+  "tool_call",
+  "tooluse",
+  "tool_use",
+  "toolcall",
+  "tooluse",
+  "functioncall",
+]);
+
+const TOOL_RESULT_TYPES = new Set(["toolresult", "tool_result"]);
+
+export function classifyMessage(message: unknown): MessageClassification {
+  const m = message as Record<string, unknown>;
+  const roleRaw = typeof m.role === "string" ? m.role : "unknown";
+  const roleLower = roleRaw.toLowerCase();
+
+  const content = Array.isArray(m.content)
+    ? (m.content as Array<Record<string, unknown>>)
+    : [];
+
+  const hasText = Boolean(extractRawText(message)?.trim());
+  const hasThinking = Boolean(extractThinking(message)?.trim());
+  const hasToolCalls = content.some((item) => {
+    const kind = String(item.type ?? "").toLowerCase();
+    if (TOOL_CALL_TYPES.has(kind)) return true;
+    return typeof item.name === "string" && (item.arguments ?? item.args ?? item.input) != null;
+  });
+  const hasToolResults = content.some((item) =>
+    TOOL_RESULT_TYPES.has(String(item.type ?? "").toLowerCase()),
+  );
+
+  const hasToolId =
+    typeof m.toolCallId === "string" ||
+    typeof m.tool_call_id === "string" ||
+    typeof m.toolUseId === "string" ||
+    typeof m.tool_use_id === "string";
+  const hasToolName =
+    typeof m.toolName === "string" || typeof m.tool_name === "string";
+
+  const isRoleTool =
+    roleLower === "tool" ||
+    roleLower === "toolresult" ||
+    roleLower === "tool_result" ||
+    roleLower === "function";
+
+  const isToolLike =
+    isRoleTool || hasToolId || hasToolName || hasToolCalls || hasToolResults;
+
+  let roleKind: RoleKind;
+  if (roleLower === "user") {
+    roleKind = "user";
+  } else if (roleLower === "assistant") {
+    roleKind = isToolLike && !hasText ? "tool" : "assistant";
+  } else if (roleLower === "system") {
+    roleKind = "system";
+  } else if (isRoleTool) {
+    roleKind = "tool";
+  } else if (isToolLike && !hasText) {
+    roleKind = "tool";
+  } else {
+    roleKind = "other";
+  }
+
+  const displayLabel =
+    roleKind === "assistant"
+      ? "Assistant"
+      : roleKind === "user"
+        ? "You"
+        : roleKind === "tool"
+          ? "Tool"
+          : roleKind === "system"
+            ? "System"
+            : roleRaw;
+
+  return {
+    roleRaw,
+    roleKind,
+    hasText,
+    hasThinking,
+    hasToolCalls,
+    hasToolResults,
+    isToolLike,
+    displayLabel,
+  };
+}
diff --git a/ui/src/ui/chat/message-normalizer.test.ts b/ui/src/ui/chat/message-normalizer.test.ts
index 132a4be17..f409c2511 100644
--- a/ui/src/ui/chat/message-normalizer.test.ts
+++ b/ui/src/ui/chat/message-normalizer.test.ts
@@ -1,9 +1,6 @@
 import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
-import {
-  normalizeMessage,
-  normalizeRoleForGrouping,
-  isToolResultMessage,
-} from "./message-normalizer";
+import { normalizeMessage } from "./message-normalizer";
+import { classifyMessage } from "./message-classifier";
 
 describe("message-normalizer", () => {
   describe("normalizeMessage", () => {
@@ -57,24 +54,24 @@ describe("message-normalizer", () => {
       expect(result.content).toEqual([{ type: "text", text: "Alternative format" }]);
     });
 
-    it("detects tool result by toolCallId", () => {
+    it("preserves role when toolCallId is present", () => {
       const result = normalizeMessage({
         role: "assistant",
         toolCallId: "call-123",
         content: "Tool output",
       });
 
-      expect(result.role).toBe("toolResult");
+      expect(result.role).toBe("assistant");
     });
 
-    it("detects tool result by tool_call_id (snake_case)", () => {
+    it("preserves role when tool_call_id is present", () => {
       const result = normalizeMessage({
         role: "assistant",
         tool_call_id: "call-456",
         content: "Tool output",
       });
 
-      expect(result.role).toBe("toolResult");
+      expect(result.role).toBe("assistant");
     });
 
     it("handles missing role", () => {
@@ -102,68 +99,54 @@ describe("message-normalizer", () => {
     });
   });
 
-  describe("normalizeRoleForGrouping", () => {
-    it("returns tool for toolresult", () => {
-      expect(normalizeRoleForGrouping("toolresult")).toBe("tool");
-      expect(normalizeRoleForGrouping("toolResult")).toBe("tool");
-      expect(normalizeRoleForGrouping("TOOLRESULT")).toBe("tool");
+  describe("classifyMessage", () => {
+    it("keeps assistant role when text + tool blocks are mixed", () => {
+      const result = classifyMessage({
+        role: "assistant",
+        content: [
+          { type: "text", text: "before" },
+          { type: "toolCall", id: "call_1", name: "read", arguments: {} },
+          { type: "thinking", thinking: "after" },
+          { type: "text", text: "after text" },
+        ],
+      });
+
+      expect(result.roleKind).toBe("assistant");
+      expect(result.hasText).toBe(true);
+      expect(result.hasToolCalls).toBe(true);
+      expect(result.hasThinking).toBe(true);
     });
 
-    it("returns tool for tool_result", () => {
-      expect(normalizeRoleForGrouping("tool_result")).toBe("tool");
-      expect(normalizeRoleForGrouping("TOOL_RESULT")).toBe("tool");
+    it("classifies tool-only assistant messages as tool", () => {
+      const result = classifyMessage({
+        role: "assistant",
+        toolCallId: "call-1",
+        content: [{ type: "toolCall", id: "call-1", name: "read" }],
+      });
+
+      expect(result.roleKind).toBe("tool");
+      expect(result.hasText).toBe(false);
+      expect(result.isToolLike).toBe(true);
     });
 
-    it("returns tool for tool", () => {
-      expect(normalizeRoleForGrouping("tool")).toBe("tool");
-      expect(normalizeRoleForGrouping("Tool")).toBe("tool");
+    it("classifies tool role messages as tool", () => {
+      const result = classifyMessage({
+        role: "tool",
+        content: "Sunny, 70F.",
+      });
+
+      expect(result.roleKind).toBe("tool");
+      expect(result.hasText).toBe(true);
     });
 
-    it("returns tool for function", () => {
-      expect(normalizeRoleForGrouping("function")).toBe("tool");
-      expect(normalizeRoleForGrouping("Function")).toBe("tool");
-    });
+    it("classifies toolResult role messages as tool", () => {
+      const result = classifyMessage({
+        role: "toolResult",
+        content: [{ type: "text", text: "ok" }],
+      });
 
-    it("preserves user role", () => {
-      expect(normalizeRoleForGrouping("user")).toBe("user");
-      expect(normalizeRoleForGrouping("User")).toBe("User");
-    });
-
-    it("preserves assistant role", () => {
-      expect(normalizeRoleForGrouping("assistant")).toBe("assistant");
-    });
-
-    it("preserves system role", () => {
-      expect(normalizeRoleForGrouping("system")).toBe("system");
-    });
-  });
-
-  describe("isToolResultMessage", () => {
-    it("returns true for toolresult role", () => {
-      expect(isToolResultMessage({ role: "toolresult" })).toBe(true);
-      expect(isToolResultMessage({ role: "toolResult" })).toBe(true);
-      expect(isToolResultMessage({ role: "TOOLRESULT" })).toBe(true);
-    });
-
-    it("returns true for tool_result role", () => {
-      expect(isToolResultMessage({ role: "tool_result" })).toBe(true);
-      expect(isToolResultMessage({ role: "TOOL_RESULT" })).toBe(true);
-    });
-
-    it("returns false for other roles", () => {
-      expect(isToolResultMessage({ role: "user" })).toBe(false);
-      expect(isToolResultMessage({ role: "assistant" })).toBe(false);
-      expect(isToolResultMessage({ role: "tool" })).toBe(false);
-    });
-
-    it("returns false for missing role", () => {
-      expect(isToolResultMessage({})).toBe(false);
-      expect(isToolResultMessage({ content: "test" })).toBe(false);
-    });
-
-    it("returns false for non-string role", () => {
-      expect(isToolResultMessage({ role: 123 })).toBe(false);
-      expect(isToolResultMessage({ role: null })).toBe(false);
+      expect(result.roleKind).toBe("tool");
+      expect(result.isToolLike).toBe(true);
     });
   });
 });
diff --git a/ui/src/ui/chat/message-normalizer.ts b/ui/src/ui/chat/message-normalizer.ts
index aa7b39d5c..43df2e864 100644
--- a/ui/src/ui/chat/message-normalizer.ts
+++ b/ui/src/ui/chat/message-normalizer.ts
@@ -12,40 +12,7 @@ import type {
  */
 export function normalizeMessage(message: unknown): NormalizedMessage {
   const m = message as Record<string, unknown>;
-  let role = typeof m.role === "string" ? m.role : "unknown";
-
-  // Detect tool messages by common gateway shapes.
-  // Some tool events come through as assistant role with tool_* items in the content array.
-  const hasToolId =
-    typeof m.toolCallId === "string" || typeof m.tool_call_id === "string";
-
-  const contentRaw = m.content;
-  const contentItems = Array.isArray(contentRaw) ? contentRaw : null;
-  const hasToolContent =
-    Array.isArray(contentItems) &&
-    contentItems.some((item) => {
-      const x = item as Record<string, unknown>;
-      const t = String(x.type ?? "").toLowerCase();
-      return (
-        t === "toolcall" ||
-        t === "tool_call" ||
-        t === "tooluse" ||
-        t === "tool_use" ||
-        t === "toolresult" ||
-        t === "tool_result" ||
-        t === "tool_call" ||
-        t === "tool_result" ||
-        (typeof x.name === "string" && x.arguments != null)
-      );
-    });
-
-  const hasToolName =
-    typeof (m as Record<string, unknown>).toolName === "string" ||
-    typeof (m as Record<string, unknown>).tool_name === "string";
-
-  if (hasToolId || hasToolContent || hasToolName) {
-    role = "toolResult";
-  }
+  const role = typeof m.role === "string" ? m.role : "unknown";
 
   // Extract content
   let content: MessageContentItem[] = [];
@@ -68,33 +35,3 @@ export function normalizeMessage(message: unknown): NormalizedMessage {
 
   return { role, content, timestamp, id };
 }
-
-/**
- * Normalize role for grouping purposes.
- */
-export function normalizeRoleForGrouping(role: string): string {
-  const lower = role.toLowerCase();
-  // Keep tool-related roles distinct so the UI can style/toggle them.
-  if (
-    lower === "toolresult" ||
-    lower === "tool_result" ||
-    lower === "tool" ||
-    lower === "function" ||
-    lower === "toolresult"
-  ) {
-    return "tool";
-  }
-  if (lower === "assistant") return "assistant";
-  if (lower === "user") return "user";
-  if (lower === "system") return "system";
-  return role;
-}
-
-/**
- * Check if a message is a tool result message based on its role.
- */
-export function isToolResultMessage(message: unknown): boolean {
-  const m = message as Record<string, unknown>;
-  const role = typeof m.role === "string" ? m.role.toLowerCase() : "";
-  return role === "toolresult" || role === "tool_result";
-}
diff --git a/ui/src/ui/chat/tool-cards.ts b/ui/src/ui/chat/tool-cards.ts
index f725363df..4bc25f54d 100644
--- a/ui/src/ui/chat/tool-cards.ts
+++ b/ui/src/ui/chat/tool-cards.ts
@@ -9,7 +9,7 @@ import {
   formatToolOutputForSidebar,
   getTruncatedPreview,
 } from "./tool-helpers";
-import { isToolResultMessage } from "./message-normalizer";
+import { classifyMessage } from "./message-classifier";
 import { extractText } from "./message-extract";
 
 export function extractToolCards(message: unknown): ToolCard[] {
@@ -39,10 +39,13 @@ export function extractToolCards(message: unknown): ToolCard[] {
     cards.push({ kind: "result", name, text });
   }
 
-  if (
-    isToolResultMessage(message) &&
-    !cards.some((card) => card.kind === "result")
-  ) {
+  const classification = classifyMessage(message);
+  const isToolResultMessage =
+    classification.hasToolResults ||
+    classification.roleRaw.toLowerCase() === "toolresult" ||
+    classification.roleRaw.toLowerCase() === "tool_result";
+
+  if (isToolResultMessage && !cards.some((card) => card.kind === "result")) {
     const name =
       (typeof m.toolName === "string" && m.toolName) ||
       (typeof m.tool_name === "string" && m.tool_name) ||
@@ -197,4 +200,3 @@ function extractToolText(item: Record<string, unknown>): string | undefined {
   if (typeof item.content === "string") return item.content;
   return undefined;
 }
-
diff --git a/ui/src/ui/views/chat.ts b/ui/src/ui/views/chat.ts
index f25221db5..d10f57815 100644
--- a/ui/src/ui/views/chat.ts
+++ b/ui/src/ui/views/chat.ts
@@ -3,10 +3,8 @@ import { repeat } from "lit/directives/repeat.js";
 import type { SessionsListResult } from "../types";
 import type { ChatQueueItem } from "../ui-types";
 import type { ChatItem, MessageGroup } from "../types/chat-types";
-import {
-  normalizeMessage,
-  normalizeRoleForGrouping,
-} from "../chat/message-normalizer";
+import { normalizeMessage } from "../chat/message-normalizer";
+import { classifyMessage } from "../chat/message-classifier";
 import { extractText } from "../chat/message-extract";
 import { renderMessage, renderReadingIndicator } from "../chat/legacy-render";
 import {
@@ -272,7 +270,8 @@ function groupMessages(items: ChatItem[]): Array<ChatItem | MessageGroup> {
     }
 
     const normalized = normalizeMessage(item.message);
-    const role = normalizeRoleForGrouping(normalized.role);
+    const classification = classifyMessage(item.message);
+    const role = classification.roleKind;
     const timestamp = normalized.timestamp || Date.now();
 
     if (!currentGroup || currentGroup.role !== role) {
@@ -312,26 +311,18 @@ function buildChatItems(props: ChatProps): Array<ChatItem | MessageGroup> {
   }
   for (let i = historyStart; i < history.length; i++) {
     const msg = history[i];
-    const normalized = normalizeMessage(msg);
-
-    if (!props.showThinking && normalized.role.toLowerCase() === "toolresult") {
-      continue;
-    }
-
     items.push({
       kind: "message",
       key: messageKey(msg, i),
       message: msg,
     });
   }
-  if (props.showThinking) {
-    for (let i = 0; i < tools.length; i++) {
-      items.push({
-        kind: "message",
-        key: messageKey(tools[i], i + history.length),
-        message: tools[i],
-      });
-    }
+  for (let i = 0; i < tools.length; i++) {
+    items.push({
+      kind: "message",
+      key: messageKey(tools[i], i + history.length),
+      message: tools[i],
+    });
   }
 
   if (props.stream !== null) {