diff --git a/tools/builders/web-builder.js b/tools/builders/web-builder.js
index bac8ea0c..9ed8bd99 100644
--- a/tools/builders/web-builder.js
+++ b/tools/builders/web-builder.js
@@ -519,9 +519,32 @@ class WebBuilder {
      * Ensure sample update directory exists
      */
     ensureSampleUpdateDirectory() {
+        // Clean existing files in web-bundles subdirectories
+        const teamsDir = path.join(this.sampleUpdatePath, 'teams');
+        const agentsDir = path.join(this.sampleUpdatePath, 'agents');
+        
+        // Remove existing .txt files in teams directory
+        if (fs.existsSync(teamsDir)) {
+            const teamFiles = fs.readdirSync(teamsDir).filter(f => f.endsWith('.txt'));
+            teamFiles.forEach(file => {
+                fs.unlinkSync(path.join(teamsDir, file));
+            });
+            console.log(`🧹 Cleaned ${teamFiles.length} files from web-bundles/teams`);
+        }
+        
+        // Remove existing .txt files in agents directory
+        if (fs.existsSync(agentsDir)) {
+            const agentFiles = fs.readdirSync(agentsDir).filter(f => f.endsWith('.txt'));
+            agentFiles.forEach(file => {
+                fs.unlinkSync(path.join(agentsDir, file));
+            });
+            console.log(`🧹 Cleaned ${agentFiles.length} files from web-bundles/agents`);
+        }
+        
+        // Ensure directories exist
         this.ensureDirectory(this.sampleUpdatePath);
-        this.ensureDirectory(path.join(this.sampleUpdatePath, 'teams'));
-        this.ensureDirectory(path.join(this.sampleUpdatePath, 'agents'));
+        this.ensureDirectory(teamsDir);
+        this.ensureDirectory(agentsDir);
     }
 }
 
diff --git a/web-bundles/teams/team-all.txt b/web-bundles/teams/team-all.txt
index 292567fc..e6bdfac2 100644
--- a/web-bundles/teams/team-all.txt
+++ b/web-bundles/teams/team-all.txt
@@ -87,7 +87,7 @@
 
 
 <!-- Bundle: Team All -->
-<!-- Generated: 2025-06-09T03:59:32.709Z -->
+<!-- Generated: 2025-06-09T04:05:51.750Z -->
 <!-- Environment: web -->
 
 ==================== START: agent-config ====================
diff --git a/web-bundles/teams/team-fullstack.txt b/web-bundles/teams/team-fullstack.txt
index e82f9f44..5bc8ec7c 100644
--- a/web-bundles/teams/team-fullstack.txt
+++ b/web-bundles/teams/team-fullstack.txt
@@ -67,7 +67,7 @@
 
 
 <!-- Bundle: Team Fullstack -->
-<!-- Generated: 2025-06-09T03:59:32.719Z -->
+<!-- Generated: 2025-06-09T04:05:51.754Z -->
 <!-- Environment: web -->
 
 ==================== START: agent-config ====================
diff --git a/web-bundles/teams/team-no-ui.txt b/web-bundles/teams/team-no-ui.txt
index 178540aa..ace4dfec 100644
--- a/web-bundles/teams/team-no-ui.txt
+++ b/web-bundles/teams/team-no-ui.txt
@@ -61,7 +61,7 @@
 
 
 <!-- Bundle: Team No UI -->
-<!-- Generated: 2025-06-09T03:59:32.721Z -->
+<!-- Generated: 2025-06-09T04:05:51.757Z -->
 <!-- Environment: web -->
 
 ==================== START: agent-config ====================
diff --git a/web-bundles/teams/team-scrum.txt b/web-bundles/teams/team-scrum.txt
index 03f0dbc2..0e8cdf4d 100644
--- a/web-bundles/teams/team-scrum.txt
+++ b/web-bundles/teams/team-scrum.txt
@@ -60,7 +60,7 @@
 
 
 <!-- Bundle: Team Scrum -->
-<!-- Generated: 2025-06-09T03:59:32.723Z -->
+<!-- Generated: 2025-06-09T04:05:51.759Z -->
 <!-- Environment: web -->
 
 ==================== START: agent-config ====================
diff --git a/web-bundles/teams/team-technical.txt b/web-bundles/teams/team-technical.txt
index 767d3412..99120317 100644
--- a/web-bundles/teams/team-technical.txt
+++ b/web-bundles/teams/team-technical.txt
@@ -58,7 +58,7 @@
 
 
 <!-- Bundle: team-technical -->
-<!-- Generated: 2025-06-09T03:59:32.724Z -->
+<!-- Generated: 2025-06-09T04:05:51.761Z -->
 <!-- Environment: web -->
 
 ==================== START: agent-config ====================