diff --git a/packages/cli/src/services/insight/generators/DataProcessor.ts b/packages/cli/src/services/insight/generators/DataProcessor.ts
index 4120561be..a3cda424e 100644
--- a/packages/cli/src/services/insight/generators/DataProcessor.ts
+++ b/packages/cli/src/services/insight/generators/DataProcessor.ts
@@ -284,20 +284,20 @@ export class DataProcessor {
     facetsOutputDir?: string,
     onProgress?: InsightProgressCallback,
   ): Promise<InsightData> {
-    if (onProgress) onProgress('Scanning chat files', 0);
+    if (onProgress) onProgress('Scanning chat history...', 0);
     const allChatFiles = await this.scanChatFiles(baseDir);
 
-    if (onProgress) onProgress('Generating metrics', 10);
+    if (onProgress) onProgress('Crunching the numbers', 10);
     const metrics = await this.generateMetrics(allChatFiles, onProgress);
 
-    if (onProgress) onProgress('Analyzing sessions', 20);
+    if (onProgress) onProgress('Preparing sessions...', 20);
     const facets = await this.generateFacets(
       allChatFiles,
       facetsOutputDir,
       onProgress,
     );
 
-    if (onProgress) onProgress('Generating qualitative insights', 80);
+    if (onProgress) onProgress('Generating personalized insights...', 80);
     const qualitative = await this.generateQualitativeInsights(metrics, facets);
 
     // Aggregate satisfaction, friction, success and outcome data from facets
@@ -309,7 +309,7 @@ export class DataProcessor {
       goalsAgg,
     } = this.aggregateFacetsData(facets);
 
-    if (onProgress) onProgress('Finalizing report', 100);
+    if (onProgress) onProgress('Assembling report...', 100);
 
     return {
       ...metrics,
@@ -924,7 +924,7 @@ None captured`;
         const percentComplete = batchEnd / totalFiles;
         const overallProgress = 10 + Math.round(percentComplete * 10);
         onProgress(
-          `Generating metrics (${batchEnd}/${totalFiles})`,
+          `Crunching the numbers (${batchEnd}/${totalFiles})`,
           overallProgress,
         );
       }
diff --git a/packages/cli/src/ui/commands/insightCommand.ts b/packages/cli/src/ui/commands/insightCommand.ts
index 3ed78710f..1693254bb 100644
--- a/packages/cli/src/ui/commands/insightCommand.ts
+++ b/packages/cli/src/ui/commands/insightCommand.ts
@@ -53,6 +53,14 @@ export const insightCommand: SlashCommand = {
         context.ui.setPendingItem(progressItem);
       };
 
+      context.ui.addItem(
+        {
+          type: MessageType.INFO,
+          text: t('This may take a couple minutes. Sit tight!'),
+        },
+        Date.now(),
+      );
+
       // Initial progress
       updateProgress(t('Starting insight generation...'), 0);
 
diff --git a/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx b/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx
index befd3ebfa..4115b3899 100644
--- a/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx
+++ b/packages/cli/src/ui/components/messages/InsightProgressMessage.tsx
@@ -44,18 +44,16 @@ export const InsightProgressMessage: React.FC<InsightProgressMessageProps> = ({
   }
 
   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>
+    <Box flexDirection="row">
+      <Text color={theme.text.accent}>
+        <Spinner type="dots" />
+      </Text>
+      <Text> </Text>
+      <Text color={theme.text.secondary}>{bar} </Text>
+      <Text color={theme.text.accent}>
+        {stage}
+        {progress.detail ? ` (${progress.detail})` : ''}
+      </Text>
     </Box>
   );
 };