diff --git a/packages/cli/src/services/insight/generators/DataProcessor.ts b/packages/cli/src/services/insight/generators/DataProcessor.ts
index e84157780..8e33b7ae4 100644
--- a/packages/cli/src/services/insight/generators/DataProcessor.ts
+++ b/packages/cli/src/services/insight/generators/DataProcessor.ts
@@ -14,6 +14,7 @@ import type {
   HeatMapData,
   StreakData,
   SessionFacets,
+  InsightProgressCallback,
 } from '../types/StaticInsightTypes.js';
 import type {
   QualitativeInsights,
@@ -262,19 +263,29 @@ export class DataProcessor {
   async generateInsights(
     baseDir: string,
     facetsOutputDir?: string,
+    onProgress?: InsightProgressCallback,
   ): Promise<InsightData> {
+    if (onProgress) onProgress('Scanning chat files', 0);
     const allChatFiles = await this.scanChatFiles(baseDir);
 
-    const [metrics, facets] = await Promise.all([
-      this.generateMetrics(allChatFiles),
-      this.generateFacets(allChatFiles, facetsOutputDir),
-    ]);
+    if (onProgress) onProgress('Generating metrics', 10);
+    const metrics = await this.generateMetrics(allChatFiles);
 
+    if (onProgress) onProgress('Analyzing sessions', 20);
+    const facets = await this.generateFacets(
+      allChatFiles,
+      facetsOutputDir,
+      onProgress,
+    );
+
+    if (onProgress) onProgress('Generating qualitative insights', 80);
     const qualitative = await this.generateQualitativeInsights(metrics, facets);
 
     // Aggregate satisfaction and friction data from facets
     const { satisfactionAgg, frictionAgg } = this.aggregateFacetsData(facets);
 
+    if (onProgress) onProgress('Finalizing report', 100);
+
     return {
       ...metrics,
       qualitative,
@@ -901,6 +912,7 @@ None captured`;
   private async generateFacets(
     allFiles: Array<{ path: string; mtime: number }>,
     facetsOutputDir?: string,
+    onProgress?: InsightProgressCallback,
   ): Promise<SessionFacets[]> {
     // Sort files by recency (descending) and take top 50
     const recentFiles = [...allFiles]
@@ -912,6 +924,9 @@ None captured`;
     // Create a limit function with concurrency of 4 to avoid 429 errors
     const limit = pLimit(4);
 
+    let completed = 0;
+    const total = recentFiles.length;
+
     // Analyze sessions concurrently with limit
     const analysisPromises = recentFiles.map((fileInfo) =>
       limit(async () => {
@@ -933,6 +948,15 @@ None captured`;
                   'utf-8',
                 );
                 const existingFacet = JSON.parse(existingData);
+                completed++;
+                if (onProgress) {
+                  const percent = 20 + Math.round((completed / total) * 60);
+                  onProgress(
+                    'Analyzing sessions',
+                    percent,
+                    `${completed}/${total}`,
+                  );
+                }
                 return existingFacet;
               } catch (readError) {
                 // File doesn't exist or is invalid, proceed to analyze
@@ -967,9 +991,20 @@ None captured`;
             }
           }
 
+          completed++;
+          if (onProgress) {
+            const percent = 20 + Math.round((completed / total) * 60);
+            onProgress('Analyzing sessions', percent, `${completed}/${total}`);
+          }
+
           return facet;
         } catch (e) {
           console.error(`Error analyzing session file ${fileInfo.path}:`, e);
+          completed++;
+          if (onProgress) {
+            const percent = 20 + Math.round((completed / total) * 60);
+            onProgress('Analyzing sessions', percent, `${completed}/${total}`);
+          }
           return null;
         }
       }),
diff --git a/packages/cli/src/services/insight/generators/StaticInsightGenerator.ts b/packages/cli/src/services/insight/generators/StaticInsightGenerator.ts
index b6e538084..bd98331e4 100644
--- a/packages/cli/src/services/insight/generators/StaticInsightGenerator.ts
+++ b/packages/cli/src/services/insight/generators/StaticInsightGenerator.ts
@@ -9,7 +9,10 @@ import path from 'path';
 import os from 'os';
 import { DataProcessor } from './DataProcessor.js';
 import { TemplateRenderer } from './TemplateRenderer.js';
-import type { InsightData } from '../types/StaticInsightTypes.js';
+import type {
+  InsightData,
+  InsightProgressCallback,
+} from '../types/StaticInsightTypes.js';
 
 import type { Config } from '@qwen-code/qwen-code-core';
 
@@ -30,7 +33,10 @@ export class StaticInsightGenerator {
   }
 
   // Generate the static insight HTML file
-  async generateStaticInsight(baseDir: string): Promise<string> {
+  async generateStaticInsight(
+    baseDir: string,
+    onProgress?: InsightProgressCallback,
+  ): Promise<string> {
     try {
       // Ensure output directory exists
       const outputDir = await this.ensureOutputDirectory();
@@ -42,6 +48,7 @@ export class StaticInsightGenerator {
       const insights: InsightData = await this.dataProcessor.generateInsights(
         baseDir,
         facetsDir,
+        onProgress,
       );
 
       // Render HTML
diff --git a/packages/cli/src/services/insight/types/StaticInsightTypes.ts b/packages/cli/src/services/insight/types/StaticInsightTypes.ts
index 2b66357c0..392b3fabe 100644
--- a/packages/cli/src/services/insight/types/StaticInsightTypes.ts
+++ b/packages/cli/src/services/insight/types/StaticInsightTypes.ts
@@ -79,3 +79,9 @@ export interface StaticInsightTemplateData {
   scripts: string;
   generatedTime: string;
 }
+
+export type InsightProgressCallback = (
+  stage: string,
+  progress: number,
+  detail?: string,
+) => void;
diff --git a/packages/cli/src/ui/commands/insightCommand.ts b/packages/cli/src/ui/commands/insightCommand.ts
index 04a0497e1..7e293dba4 100644
--- a/packages/cli/src/ui/commands/insightCommand.ts
+++ b/packages/cli/src/ui/commands/insightCommand.ts
@@ -7,6 +7,7 @@
 import type { CommandContext, SlashCommand } from './types.js';
 import { CommandKind } from './types.js';
 import { MessageType } from '../types.js';
+import type { HistoryItemInsightProgress } from '../types.js';
 import { t } from '../../i18n/index.js';
 import { join } from 'path';
 import os from 'os';
@@ -67,17 +68,33 @@ export const insightCommand: SlashCommand = {
         context.services.config,
       );
 
-      context.ui.addItem(
-        {
-          type: MessageType.INFO,
-          text: t('Processing your chat history...'),
-        },
-        Date.now(),
-      );
+      const updateProgress = (
+        stage: string,
+        progress: number,
+        detail?: string,
+      ) => {
+        const progressItem: HistoryItemInsightProgress = {
+          type: MessageType.INSIGHT_PROGRESS,
+          progress: {
+            stage,
+            progress,
+            detail,
+          },
+        };
+        context.ui.setPendingItem(progressItem);
+      };
+
+      // Initial progress
+      updateProgress(t('Starting insight generation...'), 0);
 
       // Generate the static insight HTML file
-      const outputPath =
-        await insightGenerator.generateStaticInsight(projectsDir);
+      const outputPath = await insightGenerator.generateStaticInsight(
+        projectsDir,
+        updateProgress,
+      );
+
+      // Clear pending item
+      context.ui.setPendingItem(null);
 
       context.ui.addItem(
         {
@@ -119,6 +136,9 @@ export const insightCommand: SlashCommand = {
 
       context.ui.setDebugMessage(t('Insights ready.'));
     } catch (error) {
+      // Clear pending item on error
+      context.ui.setPendingItem(null);
+
       context.ui.addItem(
         {
           type: MessageType.ERROR,
diff --git a/packages/cli/src/ui/components/HistoryItemDisplay.tsx b/packages/cli/src/ui/components/HistoryItemDisplay.tsx
index a4fa9ee7c..1b8046ac0 100644
--- a/packages/cli/src/ui/components/HistoryItemDisplay.tsx
+++ b/packages/cli/src/ui/components/HistoryItemDisplay.tsx
@@ -33,6 +33,7 @@ import { getMCPServerStatus } from '@qwen-code/qwen-code-core';
 import { SkillsList } from './views/SkillsList.js';
 import { ToolsList } from './views/ToolsList.js';
 import { McpStatus } from './views/McpStatus.js';
+import { InsightProgressMessage } from './messages/InsightProgressMessage.js';
 
 interface HistoryItemDisplayProps {
   item: HistoryItem;
@@ -176,6 +177,9 @@ const HistoryItemDisplayComponent: React.FC<HistoryItemDisplayProps> = ({
       {itemForDisplay.type === 'mcp_status' && (
         <McpStatus {...itemForDisplay} serverStatus={getMCPServerStatus} />
       )}
+      {itemForDisplay.type === 'insight_progress' && (
+        <InsightProgressMessage progress={itemForDisplay.progress} />
+      )}
     </Box>
   );
 };
diff --git a/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx b/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx
new file mode 100644
index 000000000..7f1933a21
--- /dev/null
+++ b/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx
@@ -0,0 +1,66 @@
+/**
+ * @license
+ * Copyright 2025 Qwen Code
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import type React from 'react';
+import { Box, Text } from 'ink';
+import { theme } from '../../semantic-colors.js';
+import type { InsightProgressProps } from '../../types.js';
+import Spinner from 'ink-spinner';
+
+interface InsightProgressMessageProps {
+  progress: InsightProgressProps;
+}
+
+export const InsightProgressMessage: React.FC<InsightProgressMessageProps> = ({
+  progress,
+}) => {
+  const { stage, progress: percent, detail, isComplete, error } = progress;
+  const width = 30;
+  const completedWidth = Math.round((percent / 100) * width);
+  const remainingWidth = width - completedWidth;
+
+  const bar =
+    '█'.repeat(Math.max(0, completedWidth)) +
+    '░'.repeat(Math.max(0, remainingWidth));
+
+  if (error) {
+    return (
+      <Box flexDirection="column">
+        <Text color={theme.status.error}>✕ {stage}</Text>
+        <Text color={theme.text.secondary}>{error}</Text>
+      </Box>
+    );
+  }
+
+  if (isComplete) {
+    return (
+      <Box flexDirection="row">
+        <Text color={theme.status.success}>✓ {stage}</Text>
+      </Box>
+    );
+  }
+
+  return (
+    <Box flexDirection="column">
+      <Box flexDirection="row" marginBottom={0}>
+        <Box marginRight={1}>
+          <Spinner type="dots" />
+        </Box>
+        <Text color={theme.text.accent}>{stage}</Text>
+      </Box>
+      <Box flexDirection="row" marginLeft={2}>
+        <Text color={theme.text.primary}>
+          {bar} {Math.round(percent)}%
+        </Text>
+      </Box>
+      {detail && (
+        <Box marginLeft={2}>
+          <Text color={theme.text.secondary}>{detail}</Text>
+        </Box>
+      )}
+    </Box>
+  );
+};
diff --git a/packages/cli/src/ui/hooks/slashCommandProcessor.ts b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
index 59ff06bcf..2595aa99b 100644
--- a/packages/cli/src/ui/hooks/slashCommandProcessor.ts
+++ b/packages/cli/src/ui/hooks/slashCommandProcessor.ts
@@ -181,10 +181,21 @@ export const useSlashCommandProcessor = (
           type: 'summary',
           summary: message.summary,
         };
-      } else {
+      } else if (message.type === MessageType.INSIGHT_PROGRESS) {
         historyItemContent = {
-          type: message.type,
-          text: message.content,
+          type: 'insight_progress',
+          progress: message.progress,
+        };
+      } else {
+        // At this point message should be of type { type: INFO|ERROR|USER, content: string }
+        // We cast to be sure or check existence of content
+        const msg = message as {
+          type: MessageType.INFO | MessageType.ERROR | MessageType.USER;
+          content: string;
+        };
+        historyItemContent = {
+          type: msg.type,
+          text: msg.content,
         };
       }
       addItem(historyItemContent, message.timestamp.getTime());
diff --git a/packages/cli/src/ui/types.ts b/packages/cli/src/ui/types.ts
index b111f9ac7..399bcfaef 100644
--- a/packages/cli/src/ui/types.ts
+++ b/packages/cli/src/ui/types.ts
@@ -251,6 +251,11 @@ export type HistoryItemMcpStatus = HistoryItemBase & {
   showTips: boolean;
 };
 
+export type HistoryItemInsightProgress = HistoryItemBase & {
+  type: 'insight_progress';
+  progress: InsightProgressProps;
+};
+
 // Using Omit<HistoryItem, 'id'> seems to have some issues with typescript's
 // type inference e.g. historyItem.type === 'tool_group' isn't auto-inferring that
 // 'tools' in historyItem.
@@ -278,7 +283,8 @@ export type HistoryItemWithoutId =
   | HistoryItemExtensionsList
   | HistoryItemToolsList
   | HistoryItemSkillsList
-  | HistoryItemMcpStatus;
+  | HistoryItemMcpStatus
+  | HistoryItemInsightProgress;
 
 export type HistoryItem = HistoryItemWithoutId & { id: number };
 
@@ -301,6 +307,15 @@ export enum MessageType {
   TOOLS_LIST = 'tools_list',
   SKILLS_LIST = 'skills_list',
   MCP_STATUS = 'mcp_status',
+  INSIGHT_PROGRESS = 'insight_progress',
+}
+
+export interface InsightProgressProps {
+  stage: string;
+  progress: number;
+  detail?: string;
+  isComplete?: boolean;
+  error?: string;
 }
 
 // Simplified message structure for internal feedback
@@ -367,6 +382,11 @@ export type Message =
       type: MessageType.SUMMARY;
       summary: SummaryProps;
       timestamp: Date;
+    }
+  | {
+      type: MessageType.INSIGHT_PROGRESS;
+      progress: InsightProgressProps;
+      timestamp: Date;
     };
 
 export interface ConsoleMessageItem {