diff --git a/packages/cli/src/services/BuiltinCommandLoader.ts b/packages/cli/src/services/BuiltinCommandLoader.ts
index 0ae9ef3598..f18330f672 100644
--- a/packages/cli/src/services/BuiltinCommandLoader.ts
+++ b/packages/cli/src/services/BuiltinCommandLoader.ts
@@ -31,6 +31,7 @@ import { directoryCommand } from '../ui/commands/directoryCommand.js';
 import { editorCommand } from '../ui/commands/editorCommand.js';
 import { extensionsCommand } from '../ui/commands/extensionsCommand.js';
 import { helpCommand } from '../ui/commands/helpCommand.js';
+import { insightsCommand } from '../ui/commands/insightsCommand.js';
 import { shortcutsCommand } from '../ui/commands/shortcutsCommand.js';
 import { rewindCommand } from '../ui/commands/rewindCommand.js';
 import { hooksCommand } from '../ui/commands/hooksCommand.js';
@@ -117,6 +118,7 @@ export class BuiltinCommandLoader implements ICommandLoader {
           ]
         : [extensionsCommand(this.config?.getEnableExtensionReloading())]),
       helpCommand,
+      insightsCommand,
       shortcutsCommand,
       ...(this.config?.getEnableHooksUI() ? [hooksCommand] : []),
       rewindCommand,
diff --git a/packages/cli/src/ui/commands/insightsCommand.ts b/packages/cli/src/ui/commands/insightsCommand.ts
new file mode 100644
index 0000000000..734344e204
--- /dev/null
+++ b/packages/cli/src/ui/commands/insightsCommand.ts
@@ -0,0 +1,56 @@
+/**
+ * @license
+ * Copyright 2025 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import { InsightsService } from '@google/gemini-cli-core';
+import { MessageType } from '../types.js';
+import {
+  type CommandContext,
+  type SlashCommand,
+  CommandKind,
+} from './types.js';
+
+/**
+ * Slash command to generate usage insights based on past sessions.
+ */
+export const insightsCommand: SlashCommand = {
+  name: 'insights',
+  description: 'Analyze past sessions and get usage improvements and summary.',
+  kind: CommandKind.BUILT_IN,
+  autoExecute: true,
+  action: async (context: CommandContext) => {
+    const config = context.services.config;
+    if (!config) {
+      context.ui.addItem({
+        type: MessageType.ERROR,
+        text: 'Config is not available.',
+      });
+      return;
+    }
+
+    context.ui.addItem({
+      type: MessageType.INFO,
+      text: 'Analyzing your past sessions to generate insights...',
+    });
+
+    try {
+      const insightsService = new InsightsService(config);
+      const baseLlmClient = config.getBaseLlmClient();
+
+      const reportMarkdown =
+        await insightsService.generateInsightsReport(baseLlmClient);
+
+      context.ui.addItem({
+        type: MessageType.GEMINI,
+        text: reportMarkdown,
+      });
+    } catch (error) {
+      context.ui.addItem({
+        type: MessageType.ERROR,
+        text: `Failed to generate insights: ${error instanceof Error ? error.message : String(error)}`,
+      });
+    }
+  },
+};
diff --git a/packages/core/src/index.ts b/packages/core/src/index.ts
index 856a896b3a..261c76dba8 100644
--- a/packages/core/src/index.ts
+++ b/packages/core/src/index.ts
@@ -109,6 +109,7 @@ export * from './services/gitService.js';
 export * from './services/chatRecordingService.js';
 export * from './services/fileSystemService.js';
 export * from './services/sessionSummaryUtils.js';
+export * from './services/insightsService.js';
 export * from './services/contextManager.js';
 export * from './skills/skillManager.js';
 export * from './skills/skillLoader.js';
diff --git a/packages/core/src/services/insightsService.ts b/packages/core/src/services/insightsService.ts
new file mode 100644
index 0000000000..861cfe7b1e
--- /dev/null
+++ b/packages/core/src/services/insightsService.ts
@@ -0,0 +1,199 @@
+/**
+ * @license
+ * Copyright 2025 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import type { Config } from '../config/config.js';
+import { Storage } from '../config/storage.js';
+import {
+  type ConversationRecord,
+  SESSION_FILE_PREFIX,
+} from './chatRecordingService.js';
+import type { BaseLlmClient } from '../core/baseLlmClient.js';
+import { getResponseText } from '../utils/partUtils.js';
+import fs from 'node:fs/promises';
+import path from 'node:path';
+import { debugLogger } from '../utils/debugLogger.js';
+
+export interface SessionMetadata {
+  projectPath: string;
+  projectName: string;
+  startTime: string;
+  summary?: string;
+  messageCount: number;
+  toolCalls: Array<{
+    name: string;
+    status: string;
+  }>;
+  errors: string[];
+}
+
+export interface InsightsReport {
+  summary: string;
+  working: string[];
+  notWorking: string[];
+  recommendations: string[];
+  fullMarkdown: string;
+}
+
+const INSIGHTS_PROMPT = `You are an expert AI productivity consultant for Gemini CLI (gcli) users.
+Analyze the following session metadata from the user's past and present GCLI sessions.
+Provide a comprehensive "Insights Report" to help the user understand their usage patterns and improve their effectiveness with the tool.
+
+Metadata:
+{metadata}
+
+The report MUST include:
+1. **Summary**: A brief (2-3 sentences) high-level overview of the user's CLI usage and general effectiveness.
+2. **What is Working**: A bulleted list of successful patterns, frequently used tools that consistently work well, and types of tasks the user is successfully completing.
+3. **What Isn't Working**: A bulleted list of recurring errors, failed tool calls, friction points, or inefficient patterns.
+4. **Recommendations**: Specific, actionable advice on how the user can improve their usage (e.g., better prompting, trying specific slash commands, managing context better).
+
+Output the report in Markdown format. Use a professional, encouraging, and highly technical tone.`;
+
+export class InsightsService {
+  constructor(private readonly config: Config) {}
+
+  /**
+   * Generates an insights report based on past and present sessions.
+   */
+  async generateInsightsReport(
+    baseLlmClient: BaseLlmClient,
+    maxSessions: number = 10,
+  ): Promise<string> {
+    const metadata = await this.collectMetadata(maxSessions);
+
+    if (metadata.length === 0) {
+      return 'No session data found to analyze. Start using Gemini CLI to get insights!';
+    }
+
+    const metadataStr = JSON.stringify(metadata, null, 2);
+    const prompt = INSIGHTS_PROMPT.replace('{metadata}', metadataStr);
+
+    try {
+      const response = await baseLlmClient.generateContent({
+        modelConfigKey: { model: 'summarizer-default' },
+        contents: [
+          {
+            role: 'user',
+            parts: [{ text: prompt }],
+          },
+        ],
+        promptId: 'insights-generation',
+        abortSignal: new AbortController().signal,
+      });
+
+      return (
+        getResponseText(response) ??
+        'Failed to generate insights report content.'
+      );
+    } catch (error) {
+      debugLogger.error('Error generating insights report:', error);
+      throw new Error('Failed to generate insights report.');
+    }
+  }
+
+  private async collectMetadata(
+    maxSessions: number,
+  ): Promise<SessionMetadata[]> {
+    const allMetadata: SessionMetadata[] = [];
+    const globalGeminiDir = Storage.getGlobalGeminiDir();
+    const projectsFile = path.join(globalGeminiDir, 'projects.json');
+
+    let projects: Record<string, string> = {};
+    try {
+      const content = await fs.readFile(projectsFile, 'utf-8');
+      projects = JSON.parse(content).projects || {};
+    } catch (_e) {
+      debugLogger.debug('Failed to read projects.json:', _e);
+      // Fallback to current project if registry is missing
+      projects[this.config.getProjectRoot()] = 'current';
+    }
+
+    const sessionFiles: Array<{
+      filePath: string;
+      projectPath: string;
+      mtime: number;
+    }> = [];
+
+    for (const [projectPath, shortId] of Object.entries(projects)) {
+      const chatsDir = path.join(Storage.getGlobalTempDir(), shortId, 'chats');
+      try {
+        const files = await fs.readdir(chatsDir);
+        for (const file of files) {
+          if (file.startsWith(SESSION_FILE_PREFIX) && file.endsWith('.json')) {
+            const filePath = path.join(chatsDir, file);
+            const stats = await fs.stat(filePath);
+            sessionFiles.push({
+              filePath,
+              projectPath,
+              mtime: stats.mtime.getTime(),
+            });
+          }
+        }
+      } catch (_e) {
+        // Skip projects with no chats or inaccessible chats
+      }
+    }
+
+    // Sort by most recent first
+    sessionFiles.sort((a, b) => b.mtime - a.mtime);
+
+    // Take top N sessions
+    const selectedSessions = sessionFiles.slice(0, maxSessions);
+
+    for (const session of selectedSessions) {
+      try {
+        const content = await fs.readFile(session.filePath, 'utf-8');
+        const conversation: ConversationRecord = JSON.parse(content);
+        allMetadata.push(
+          this.extractSessionMetadata(conversation, session.projectPath),
+        );
+      } catch (_e) {
+        debugLogger.debug(
+          `Failed to parse session file ${session.filePath}:`,
+          _e,
+        );
+      }
+    }
+
+    return allMetadata;
+  }
+
+  private extractSessionMetadata(
+    conversation: ConversationRecord,
+    projectPath: string,
+  ): SessionMetadata {
+    const toolCalls: Array<{ name: string; status: string }> = [];
+    const errors: string[] = [];
+
+    for (const msg of conversation.messages) {
+      if (msg.type === 'gemini' && msg.toolCalls) {
+        for (const tc of msg.toolCalls) {
+          toolCalls.push({
+            name: tc.name,
+            status: tc.status,
+          });
+        }
+      }
+      if (msg.type === 'error') {
+        const errorText =
+          typeof msg.content === 'string'
+            ? msg.content
+            : JSON.stringify(msg.content);
+        errors.push(errorText.slice(0, 200)); // Limit error length
+      }
+    }
+
+    return {
+      projectPath,
+      projectName: path.basename(projectPath),
+      startTime: conversation.startTime,
+      summary: conversation.summary,
+      messageCount: conversation.messages.length,
+      toolCalls,
+      errors: errors.slice(0, 5), // Limit number of errors
+    };
+  }
+}