diff --git a/src/agent/cli/output.test.ts b/src/agent/cli/output.test.ts
index 3a6f6030..f292dd0e 100644
--- a/src/agent/cli/output.test.ts
+++ b/src/agent/cli/output.test.ts
@@ -112,6 +112,14 @@ describe("output", () => {
       expect(extractResultDetails(result)).toEqual(result);
     });
 
+    it("should prefer details when present", () => {
+      const result = {
+        content: [{ type: "text", text: "not json" }],
+        details: { count: 3, truncated: false },
+      };
+      expect(extractResultDetails(result)).toEqual({ count: 3, truncated: false });
+    });
+
     it("should return direct object if no content array", () => {
       const result = { count: 10, truncated: true };
       expect(extractResultDetails(result)).toEqual({ count: 10, truncated: true });
diff --git a/src/agent/cli/output.ts b/src/agent/cli/output.ts
index 3c6c9835..f7b2437d 100644
--- a/src/agent/cli/output.ts
+++ b/src/agent/cli/output.ts
@@ -118,6 +118,11 @@ export function extractResultDetails(result: unknown): Record<string, unknown> |
     }
   }
 
+  const withDetails = result as { details?: unknown };
+  if (withDetails.details && typeof withDetails.details === "object") {
+    return withDetails.details as Record<string, unknown>;
+  }
+
   // Try direct object access
   return result as Record<string, unknown>;
 }
@@ -252,8 +257,18 @@ export function createAgentOutput(params: {
       }
       case "tool_execution_end": {
         // Stop spinner and show final result with summary
-        if (event.isError) {
-          const errorText = extractText(event.result) || "Tool failed";
+        const details = extractResultDetails(event.result);
+        const errorField = details?.error;
+        const hasError =
+          event.isError ||
+          Boolean(errorField) ||
+          details?.success === false;
+        if (hasError) {
+          const errorText =
+            (typeof details?.message === "string" && details.message) ||
+            (typeof errorField === "string" && errorField) ||
+            extractText(event.result) ||
+            "Tool failed";
           const bullet = colors.toolError("✗");
           const title = colors.toolName(toolDisplayName(event.toolName));
           spinner.stop(`${bullet} ${title}: ${colors.toolError(errorText)}`);
diff --git a/src/agent/tools.ts b/src/agent/tools.ts
index 6578a238..967a2d54 100644
--- a/src/agent/tools.ts
+++ b/src/agent/tools.ts
@@ -1,13 +1,14 @@
 import type { AgentOptions } from "./types.js";
 import { getModel } from "@mariozechner/pi-ai";
 import { createCodingTools } from "@mariozechner/pi-coding-agent";
-import type { AgentTool } from "@mariozechner/pi-agent-core";
+import type { AgentTool, AgentToolResult } from "@mariozechner/pi-agent-core";
 import { createExecTool } from "./tools/exec.js";
 import { createProcessTool } from "./tools/process.js";
 import { createGlobTool } from "./tools/glob.js";
 import { createWebFetchTool, createWebSearchTool } from "./tools/web/index.js";
 import { createMemoryTools } from "./tools/memory/index.js";
 import { filterTools } from "./tools/policy.js";
+import { isMulticaError, isRetryableError } from "../shared/errors.js";
 
 export function resolveModel(options: AgentOptions) {
   if (options.provider && options.model) {
@@ -29,6 +30,66 @@ export interface CreateToolsOptions {
   profileBaseDir?: string;
 }
 
+type ToolErrorPayload = {
+  error: true;
+  message: string;
+  name?: string;
+  code?: string;
+  retryable?: boolean;
+  details?: Record<string, unknown>;
+};
+
+function toToolErrorPayload(error: unknown): ToolErrorPayload {
+  if (isMulticaError(error)) {
+    return {
+      error: true,
+      message: error.message,
+      name: error.name,
+      code: error.code,
+      retryable: error.retryable,
+      details: error.details,
+    };
+  }
+
+  if (error instanceof Error) {
+    return {
+      error: true,
+      message: error.message,
+      name: error.name,
+      retryable: isRetryableError(error),
+    };
+  }
+
+  return {
+    error: true,
+    message: String(error),
+  };
+}
+
+function toolErrorResult(error: unknown): AgentToolResult<ToolErrorPayload> {
+  const payload = toToolErrorPayload(error);
+  return {
+    content: [{ type: "text", text: JSON.stringify(payload, null, 2) }],
+    details: payload,
+  };
+}
+
+function wrapTool<TParams, TResult>(
+  tool: AgentTool<TParams, TResult>,
+): AgentTool<TParams, TResult> {
+  const execute = tool.execute;
+  return {
+    ...tool,
+    execute: async (...args) => {
+      try {
+        return await execute(...args);
+      } catch (error) {
+        return toolErrorResult(error) as AgentToolResult<TResult>;
+      }
+    },
+  };
+}
+
 /**
  * Create all available tools.
  * This returns the full set before policy filtering.
@@ -95,7 +156,7 @@ export function resolveTools(options: AgentOptions): AgentTool<any>[] {
     isSubagent: options.isSubagent,
   });
 
-  return filtered;
+  return filtered.map((tool) => wrapTool(tool));
 }
 
 /**