diff --git a/web/src/client/components/session-view-drag-drop.test.ts b/web/src/client/components/session-view-drag-drop.test.ts
index 1fc6aa3c..702ea50c 100644
--- a/web/src/client/components/session-view-drag-drop.test.ts
+++ b/web/src/client/components/session-view-drag-drop.test.ts
@@ -227,7 +227,7 @@ describe('SessionView Drag & Drop and Paste', () => {
       expect(mockFilePicker.uploadFile).not.toHaveBeenCalled();
     });
 
-    it('should handle multiple files and pick the first one', async () => {
+    it('should handle multiple files and upload all of them', async () => {
       const textFile = new File(['text'], 'test.txt', { type: 'text/plain' });
       const jsonFile = new File(['{}'], 'test.json', { type: 'application/json' });
       const pdfFile = new File(['pdf'], 'test.pdf', { type: 'application/pdf' });
@@ -272,12 +272,15 @@ describe('SessionView Drag & Drop and Paste', () => {
 
       element.dispatchEvent(dropEvent);
 
-      // Wait for async operations
+      // Wait for all async operations to complete
       await vi.waitFor(() => {
-        expect(mockFilePicker.uploadFile).toHaveBeenCalledWith(textFile);
+        expect(mockFilePicker.uploadFile).toHaveBeenCalledTimes(3);
       });
 
-      expect(mockFilePicker.uploadFile).toHaveBeenCalledTimes(1);
+      // Verify all files were uploaded in order
+      expect(mockFilePicker.uploadFile).toHaveBeenNthCalledWith(1, textFile);
+      expect(mockFilePicker.uploadFile).toHaveBeenNthCalledWith(2, jsonFile);
+      expect(mockFilePicker.uploadFile).toHaveBeenNthCalledWith(3, pdfFile);
     });
   });
 
@@ -416,6 +419,50 @@ describe('SessionView Drag & Drop and Paste', () => {
         );
       });
     });
+
+    it('should handle multiple files pasted from clipboard', async () => {
+      const textFile = new File(['text content'], 'text.txt', { type: 'text/plain' });
+      const imageFile = new File(['image content'], 'image.png', { type: 'image/png' });
+
+      const mockClipboardItems = [
+        {
+          kind: 'file',
+          type: 'text/plain',
+          getAsFile: () => textFile,
+        },
+        {
+          kind: 'file',
+          type: 'image/png',
+          getAsFile: () => imageFile,
+        },
+      ];
+
+      const pasteEvent = new ClipboardEvent('paste', {
+        bubbles: true,
+        clipboardData: new DataTransfer(),
+      });
+
+      Object.defineProperty(pasteEvent.clipboardData, 'items', {
+        value: mockClipboardItems,
+        writable: false,
+      });
+
+      const mockFilePicker = {
+        uploadFile: vi.fn().mockResolvedValue(undefined),
+      };
+      element.querySelector = vi.fn(() => mockFilePicker);
+
+      document.dispatchEvent(pasteEvent);
+
+      // Wait for all uploads to complete
+      await vi.waitFor(() => {
+        expect(mockFilePicker.uploadFile).toHaveBeenCalledTimes(2);
+      });
+
+      // Verify both files were uploaded
+      expect(mockFilePicker.uploadFile).toHaveBeenNthCalledWith(1, textFile);
+      expect(mockFilePicker.uploadFile).toHaveBeenNthCalledWith(2, imageFile);
+    });
   });
 
   describe('Event Listener Management', () => {
diff --git a/web/src/client/components/session-view.ts b/web/src/client/components/session-view.ts
index 73bf6bab..83e3d99a 100644
--- a/web/src/client/components/session-view.ts
+++ b/web/src/client/components/session-view.ts
@@ -809,7 +809,7 @@ export class SessionView extends LitElement {
     }
   }
 
-  private handleDrop(e: DragEvent) {
+  private async handleDrop(e: DragEvent) {
     e.preventDefault();
     e.stopPropagation();
     this.isDragOver = false;
@@ -821,12 +821,19 @@ export class SessionView extends LitElement {
       return;
     }
 
-    // Upload the first file (or we could upload all of them)
-    this.uploadFile(files[0]);
+    // Upload all files sequentially
+    for (const file of files) {
+      try {
+        await this.uploadFile(file);
+        logger.log(`Successfully uploaded file: ${file.name}`);
+      } catch (error) {
+        logger.error(`Failed to upload file: ${file.name}`, error);
+      }
+    }
   }
 
   // Paste handler
-  private handlePaste(e: ClipboardEvent) {
+  private async handlePaste(e: ClipboardEvent) {
     // Only handle paste if session view is focused and no modal is open
     if (this.showFileBrowser || this.showImagePicker || this.showMobileInput) {
       return;
@@ -841,12 +848,17 @@ export class SessionView extends LitElement {
 
     e.preventDefault(); // Prevent default paste behavior for files
 
-    const fileItem = fileItems[0];
-    const file = fileItem.getAsFile();
-
-    if (file) {
-      logger.log('File pasted from clipboard');
-      this.uploadFile(file);
+    // Upload all pasted files
+    for (const fileItem of fileItems) {
+      const file = fileItem.getAsFile();
+      if (file) {
+        try {
+          await this.uploadFile(file);
+          logger.log(`Successfully pasted and uploaded file: ${file.name}`);
+        } catch (error) {
+          logger.error(`Failed to upload pasted file: ${file?.name}`, error);
+        }
+      }
     }
   }