diff --git a/gbajs3/src/components/modals/upload-rom.spec.tsx b/gbajs3/src/components/modals/upload-roms.spec.tsx
similarity index 59%
rename from gbajs3/src/components/modals/upload-rom.spec.tsx
rename to gbajs3/src/components/modals/upload-roms.spec.tsx
index 2176eca6..dbfb357a 100644
--- a/gbajs3/src/components/modals/upload-rom.spec.tsx
+++ b/gbajs3/src/components/modals/upload-roms.spec.tsx
@@ -2,7 +2,7 @@ import { screen, waitForElementToBeRemoved } from '@testing-library/react';
 import { userEvent } from '@testing-library/user-event';
 import { describe, expect, it, vi } from 'vitest';
 
-import { UploadRomModal } from './upload-rom.tsx';
+import { UploadRomsModal } from './upload-roms.tsx';
 import { testRomLocation } from '../../../test/mocks/handlers.ts';
 import { renderWithContext } from '../../../test/render-with-context.tsx';
 import * as contextHooks from '../../hooks/context.tsx';
@@ -12,7 +12,7 @@ import { productTourLocalStorageKey } from '../product-tour/consts.tsx';
 
 import type { GBAEmulator } from '../../emulator/mgba/mgba-emulator.tsx';
 
-describe('<UploadRomModal />', () => {
+describe('<UploadRomsModal />', () => {
   it('uploads file and closes modal', async () => {
     const setIsModalOpenSpy = vi.fn();
     const uploadRomSpy: (file: File, cb?: () => void) => void = vi.fn(
@@ -51,7 +51,7 @@ describe('<UploadRomModal />', () => {
 
     const testRom = new File(['Some rom file contents'], 'rom1.gba');
 
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     const romInput = screen.getByTestId('hidden-file-input');
 
@@ -67,9 +67,157 @@ describe('<UploadRomModal />', () => {
     expect(uploadRomSpy).toHaveBeenCalledOnce();
     expect(uploadRomSpy).toHaveBeenCalledWith(testRom, expect.anything());
 
+    expect(runGameSpy).toHaveBeenCalledOnce();
+    expect(runGameSpy).toHaveBeenCalledWith('rom1.gba');
     expect(syncActionIfEnabledSpy).toHaveBeenCalledOnce();
+    expect(setIsModalOpenSpy).toHaveBeenCalledOnce();
+    expect(setIsModalOpenSpy).toHaveBeenCalledWith(false);
+  });
+
+  it('uploads multiple files, loads first file, and closes modal', async () => {
+    const setIsModalOpenSpy = vi.fn();
+    const uploadRomSpy: (file: File, cb?: () => void) => void = vi.fn(
+      (_file, cb) => cb && cb()
+    );
+    const syncActionIfEnabledSpy = vi.fn();
+    const runGameSpy = vi.fn(() => true);
+
+    const {
+      useEmulatorContext: originalEmulator,
+      useModalContext: originalModal
+    } = await vi.importActual<typeof contextHooks>('../../hooks/context.tsx');
+    const { useAddCallbacks: originalCallbacks } = await vi.importActual<
+      typeof addCallbackHooks
+    >('../../hooks/emulator/use-add-callbacks.tsx');
+
+    vi.spyOn(contextHooks, 'useEmulatorContext').mockImplementation(() => ({
+      ...originalEmulator(),
+      emulator: {
+        uploadRom: uploadRomSpy
+      } as GBAEmulator
+    }));
+
+    vi.spyOn(contextHooks, 'useModalContext').mockImplementation(() => ({
+      ...originalModal(),
+      setIsModalOpen: setIsModalOpenSpy
+    }));
+
+    vi.spyOn(addCallbackHooks, 'useAddCallbacks').mockImplementation(() => ({
+      ...originalCallbacks(),
+      syncActionIfEnabled: syncActionIfEnabledSpy
+    }));
+
+    vi.spyOn(runGameHooks, 'useRunGame').mockReturnValue(runGameSpy);
+
+    const testRomFiles = [
+      new File(['Some rom file contents 1'], 'rom1.gba'),
+      new File(['Some rom file contents 2'], 'rom2.gba')
+    ];
+
+    renderWithContext(<UploadRomsModal />);
+
+    const romInput = screen.getByTestId('hidden-file-input');
+
+    expect(romInput).toBeInTheDocument();
+
+    await userEvent.upload(romInput, testRomFiles);
+
+    expect(screen.getByText('Files to upload:')).toBeVisible();
+    expect(screen.getByText('rom1.gba')).toBeVisible();
+    expect(screen.getByText('rom2.gba')).toBeVisible();
+
+    await userEvent.click(screen.getByRole('button', { name: 'Upload' }));
+
+    expect(uploadRomSpy).toHaveBeenCalledTimes(2);
+    expect(uploadRomSpy).toHaveBeenCalledWith(
+      testRomFiles[0],
+      expect.anything()
+    );
+    expect(uploadRomSpy).toHaveBeenCalledWith(
+      testRomFiles[1],
+      expect.anything()
+    );
+
     expect(runGameSpy).toHaveBeenCalledOnce();
     expect(runGameSpy).toHaveBeenCalledWith('rom1.gba');
+
+    expect(syncActionIfEnabledSpy).toHaveBeenCalledOnce();
+    expect(setIsModalOpenSpy).toHaveBeenCalledOnce();
+    expect(setIsModalOpenSpy).toHaveBeenCalledWith(false);
+  });
+
+  it('uploads multiple files, loads selected file, and closes modal', async () => {
+    const setIsModalOpenSpy = vi.fn();
+    const uploadRomSpy: (file: File, cb?: () => void) => void = vi.fn(
+      (_file, cb) => cb && cb()
+    );
+    const syncActionIfEnabledSpy = vi.fn();
+    const runGameSpy = vi.fn(() => true);
+
+    const {
+      useEmulatorContext: originalEmulator,
+      useModalContext: originalModal
+    } = await vi.importActual<typeof contextHooks>('../../hooks/context.tsx');
+    const { useAddCallbacks: originalCallbacks } = await vi.importActual<
+      typeof addCallbackHooks
+    >('../../hooks/emulator/use-add-callbacks.tsx');
+
+    vi.spyOn(contextHooks, 'useEmulatorContext').mockImplementation(() => ({
+      ...originalEmulator(),
+      emulator: {
+        uploadRom: uploadRomSpy
+      } as GBAEmulator
+    }));
+
+    vi.spyOn(contextHooks, 'useModalContext').mockImplementation(() => ({
+      ...originalModal(),
+      setIsModalOpen: setIsModalOpenSpy
+    }));
+
+    vi.spyOn(addCallbackHooks, 'useAddCallbacks').mockImplementation(() => ({
+      ...originalCallbacks(),
+      syncActionIfEnabled: syncActionIfEnabledSpy
+    }));
+
+    vi.spyOn(runGameHooks, 'useRunGame').mockReturnValue(runGameSpy);
+
+    const testRomFiles = [
+      new File(['Some rom file contents 1'], 'rom1.gba'),
+      new File(['Some rom file contents 2'], 'rom2.gba')
+    ];
+
+    renderWithContext(<UploadRomsModal />);
+
+    const romInput = screen.getByTestId('hidden-file-input');
+
+    expect(romInput).toBeInTheDocument();
+
+    await userEvent.upload(romInput, testRomFiles);
+
+    await userEvent.click(
+      screen.getByLabelText('Load rom2.gba', { selector: 'input' })
+    );
+    expect(
+      screen.getByLabelText('Load rom2.gba', { selector: 'input' })
+    ).toBeChecked();
+
+    await userEvent.click(screen.getByRole('button', { name: 'Upload' }));
+
+    expect(uploadRomSpy).toHaveBeenCalledTimes(2);
+    expect(uploadRomSpy).toHaveBeenCalledWith(
+      testRomFiles[0],
+      expect.anything()
+    );
+    expect(uploadRomSpy).toHaveBeenCalledWith(
+      testRomFiles[1],
+      expect.anything()
+    );
+
+    expect(runGameSpy).toHaveBeenCalledOnce();
+    expect(runGameSpy).toHaveBeenCalledWith('rom2.gba');
+
+    expect(syncActionIfEnabledSpy).toHaveBeenCalledOnce();
+    expect(setIsModalOpenSpy).toHaveBeenCalledOnce();
     expect(setIsModalOpenSpy).toHaveBeenCalledWith(false);
   });
 
@@ -112,7 +260,7 @@ describe('<UploadRomModal />', () => {
 
     vi.spyOn(runGameHooks, 'useRunGame').mockReturnValue(runGameSpy);
 
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     const uploadRomFromURLInput = screen.getByLabelText('Upload from a URL');
 
@@ -157,7 +305,7 @@ describe('<UploadRomModal />', () => {
       } as GBAEmulator
     }));
 
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     const uploadRomFromURLInput = screen.getByLabelText('Upload from a URL');
 
@@ -184,12 +332,27 @@ describe('<UploadRomModal />', () => {
     ).toBeVisible();
   });
 
+  it('renders invalid url error', async () => {
+    renderWithContext(<UploadRomsModal />);
+
+    await userEvent.type(
+      screen.getByLabelText('Upload from a URL'),
+      `invalid url`
+    );
+
+    await userEvent.click(screen.getByRole('button', { name: 'Upload' }));
+
+    expect(screen.getByText(/Invalid URL/)).toBeVisible();
+  });
+
   it('renders form validation error', async () => {
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     await userEvent.click(screen.getByRole('button', { name: 'Upload' }));
 
-    expect(screen.getByText(/A rom file or URL is required/)).toBeVisible();
+    expect(
+      screen.getByText(/At least one rom file or URL is required/)
+    ).toBeVisible();
   });
 
   it('closes modal using the close button', async () => {
@@ -203,7 +366,7 @@ describe('<UploadRomModal />', () => {
       setIsModalOpen: setIsModalOpenSpy
     }));
 
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     // click the close button
     const closeButton = screen.getByText('Close', { selector: 'button' });
@@ -228,7 +391,7 @@ describe('<UploadRomModal />', () => {
       '{"hasCompletedProductTourIntro":"finished"}'
     );
 
-    renderWithContext(<UploadRomModal />);
+    renderWithContext(<UploadRomsModal />);
 
     expect(
       await screen.findByText(
diff --git a/gbajs3/src/components/modals/upload-rom.tsx b/gbajs3/src/components/modals/upload-roms.tsx
similarity index 70%
rename from gbajs3/src/components/modals/upload-rom.tsx
rename to gbajs3/src/components/modals/upload-roms.tsx
index 540eb4e7..431cc9b8 100644
--- a/gbajs3/src/components/modals/upload-rom.tsx
+++ b/gbajs3/src/components/modals/upload-roms.tsx
@@ -1,4 +1,4 @@
-import { Button, Divider, TextField } from '@mui/material';
+import { Button, Divider, Checkbox, TextField } from '@mui/material';
 import { useCallback, useEffect, useId, useState } from 'react';
 import { useForm, Controller, type SubmitHandler } from 'react-hook-form';
 import { BiError } from 'react-icons/bi';
@@ -22,14 +22,41 @@ import {
   PacmanIndicator
 } from '../shared/loading-indicator.tsx';
 
+import type { CheckboxProps } from '@mui/material';
+
 type InputProps = {
-  romFile: File;
+  romFiles: File[];
+  romFileToLoad: string;
   romURL: string;
 };
 
+type AdditionalRomActionsProps = {
+  fileName: string;
+  index: number;
+  value: string;
+  totalFiles: number;
+} & Pick<CheckboxProps, 'onChange'>;
+
 const validFileExtensions = ['.gba', '.gbc', '.gb', '.zip', '.7z'];
 
-export const UploadRomModal = () => {
+const AdditionalRomActions = ({
+  fileName,
+  index,
+  totalFiles,
+  value,
+  onChange
+}: AdditionalRomActionsProps) =>
+  totalFiles && (
+    <Checkbox
+      inputProps={{ 'aria-label': `Load ${fileName}` }}
+      key={`rom_file_to_load_${fileName}_${index}`}
+      checked={fileName === value || (!value && index === 0)}
+      onChange={onChange}
+      sx={{ padding: '0 ' }}
+    />
+  );
+
+export const UploadRomsModal = () => {
   const theme = useTheme();
   const { setIsModalOpen } = useModalContext();
   const { emulator } = useEmulatorContext();
@@ -61,9 +88,7 @@ export const UploadRomModal = () => {
       const runCallback = () => {
         syncActionIfEnabled();
         const hasSucceeded = runGame(externalRomFile.name);
-        if (hasSucceeded) {
-          setIsModalOpen(false);
-        }
+        if (hasSucceeded) setIsModalOpen(false);
       };
       emulator?.uploadRom(externalRomFile, runCallback);
       setCurrentRomURL(null);
@@ -80,29 +105,42 @@ export const UploadRomModal = () => {
   const onDrop = useCallback(
     (acceptedFiles: File[]) => {
       reset();
-      setValue('romFile', acceptedFiles[0], { shouldValidate: true });
+      setValue('romFiles', acceptedFiles, { shouldValidate: true });
     },
     [reset, setValue]
   );
 
-  const onSubmit: SubmitHandler<InputProps> = async ({ romFile, romURL }) => {
+  const onSubmit: SubmitHandler<InputProps> = async ({
+    romFiles,
+    romFileToLoad,
+    romURL
+  }) => {
     if (romURL) {
       setCurrentRomURL(romURL);
       await executeLoadExternalRom({ url: new URL(romURL) });
       return;
     }
 
-    const runCallback = () => {
-      syncActionIfEnabled();
-      const hasSucceeded = runGame(romFile.name);
-      if (hasSucceeded) {
-        setIsModalOpen(false);
-      }
-    };
-    emulator?.uploadRom(romFile, runCallback);
+    await Promise.all(
+      romFiles.map(
+        (romFile, idx) =>
+          new Promise<boolean>((resolve) => {
+            const runCallback = () =>
+              resolve(
+                (romFile.name === romFileToLoad ||
+                  (!romFileToLoad && idx === 0)) &&
+                  runGame(romFile.name)
+              );
+            emulator?.uploadRom(romFile, runCallback);
+          })
+      )
+    );
+
+    syncActionIfEnabled();
+    setIsModalOpen(false);
   };
 
-  const isRomFileSet = !!watch('romFile');
+  const isRomFileSet = !!watch('romFiles')?.length;
 
   const tourSteps: TourSteps = [
     {
@@ -144,17 +182,17 @@ export const UploadRomModal = () => {
         >
           <form
             id={uploadRomFormId}
-            aria-label="Upload Rom Form"
+            aria-label="Upload Roms Form"
             onSubmit={handleSubmit(onSubmit)}
           >
             <Controller
               control={control}
-              name="romFile"
+              name="romFiles"
               rules={{
-                validate: (rom, formValues) =>
+                validate: (roms, formValues) =>
                   !!formValues.romURL ||
-                  !!rom ||
-                  'A rom file or URL is required'
+                  !!roms ||
+                  'At least one rom file or URL is required'
               }}
               render={({ field: { name }, fieldState: { error } }) => (
                 <DragAndDropInput
@@ -164,10 +202,23 @@ export const UploadRomModal = () => {
                   name={name}
                   validFileExtensions={validFileExtensions}
                   hideErrors={!!error}
+                  multiple
+                  renderAdditionalFileActions={({ fileName, ...rest }) => (
+                    <AdditionalRomActions
+                      onChange={(e) => {
+                        if (e.target.checked)
+                          setValue('romFileToLoad', fileName);
+                        else setValue('romFileToLoad', 'none');
+                      }}
+                      value={watch('romFileToLoad')}
+                      fileName={fileName}
+                      {...rest}
+                    />
+                  )}
                 >
                   <p>
-                    Drag and drop a rom or zipped rom file here, or click to
-                    upload a file
+                    Drag and drop roms or zipped rom files here, or click to
+                    upload files
                   </p>
                 </DragAndDropInput>
               )}
@@ -189,8 +240,8 @@ export const UploadRomModal = () => {
                     validate: (romURL, formValues) => {
                       if (!romURL) return true;
 
-                      if (formValues.romFile)
-                        return 'Cannot specify both a file and a URL';
+                      if (formValues.romFiles)
+                        return 'Cannot specify both files and a URL';
 
                       try {
                         new URL(romURL);
@@ -209,10 +260,10 @@ export const UploadRomModal = () => {
                 )}
               </>
             )}
-            {errors.romFile?.message && (
+            {errors.romFiles?.message && (
               <ErrorWithIcon
                 icon={<BiError style={{ color: theme.errorRed }} />}
-                text={errors.romFile.message}
+                text={errors.romFiles.message}
               />
             )}
           </form>
diff --git a/gbajs3/src/components/navigation-menu/navigation-menu.spec.tsx b/gbajs3/src/components/navigation-menu/navigation-menu.spec.tsx
index bae9ae41..256f0908 100644
--- a/gbajs3/src/components/navigation-menu/navigation-menu.spec.tsx
+++ b/gbajs3/src/components/navigation-menu/navigation-menu.spec.tsx
@@ -23,7 +23,7 @@ import { SaveStatesModal } from '../modals/save-states.tsx';
 import { UploadCheatsModal } from '../modals/upload-cheats.tsx';
 import { UploadPatchesModal } from '../modals/upload-patches.tsx';
 import { UploadRomToServerModal } from '../modals/upload-rom-to-server.tsx';
-import { UploadRomModal } from '../modals/upload-rom.tsx';
+import { UploadRomsModal } from '../modals/upload-roms.tsx';
 import { UploadSaveToServerModal } from '../modals/upload-save-to-server.tsx';
 import { UploadSavesModal } from '../modals/upload-saves.tsx';
 
@@ -90,7 +90,7 @@ describe('<NavigationMenu />', () => {
       ['Upload Saves', <UploadSavesModal />],
       ['Upload Cheats', <UploadCheatsModal />],
       ['Upload Patches', <UploadPatchesModal />],
-      ['Upload Rom', <UploadRomModal />],
+      ['Upload Roms', <UploadRomsModal />],
       ['Load Local Rom', <LoadLocalRomModal />],
       ['Controls', <ControlsModal />],
       ['File System', <FileSystemModal />],
diff --git a/gbajs3/src/components/navigation-menu/navigation-menu.tsx b/gbajs3/src/components/navigation-menu/navigation-menu.tsx
index 926f08b9..9de98cd7 100644
--- a/gbajs3/src/components/navigation-menu/navigation-menu.tsx
+++ b/gbajs3/src/components/navigation-menu/navigation-menu.tsx
@@ -50,7 +50,7 @@ import { SaveStatesModal } from '../modals/save-states.tsx';
 import { UploadCheatsModal } from '../modals/upload-cheats.tsx';
 import { UploadPatchesModal } from '../modals/upload-patches.tsx';
 import { UploadRomToServerModal } from '../modals/upload-rom-to-server.tsx';
-import { UploadRomModal } from '../modals/upload-rom.tsx';
+import { UploadRomsModal } from '../modals/upload-roms.tsx';
 import { UploadSaveToServerModal } from '../modals/upload-save-to-server.tsx';
 import { UploadSavesModal } from '../modals/upload-saves.tsx';
 import { ButtonBase } from '../shared/custom-button-base.tsx';
@@ -230,11 +230,11 @@ export const NavigationMenu = () => {
               }}
             />
             <NavLeaf
-              title="Upload Rom"
+              title="Upload Roms"
               $disabled={isRunning}
               icon={<BiUpload />}
               onClick={() => {
-                setModalContent(<UploadRomModal />);
+                setModalContent(<UploadRomsModal />);
                 setIsModalOpen(true);
               }}
             />
diff --git a/gbajs3/src/components/shared/drag-and-drop-input.tsx b/gbajs3/src/components/shared/drag-and-drop-input.tsx
index deeadda2..d0ebade5 100644
--- a/gbajs3/src/components/shared/drag-and-drop-input.tsx
+++ b/gbajs3/src/components/shared/drag-and-drop-input.tsx
@@ -24,6 +24,11 @@ type DragAndDropInputProps = {
   name: string;
   onDrop: (acceptedFiles: File[]) => void;
   validFileExtensions: Extension[];
+  renderAdditionalFileActions?: (fileInfo: {
+    fileName: string;
+    index: number;
+    totalFiles: number;
+  }) => ReactNode;
 };
 
 type DropAreaProps = {
@@ -85,31 +90,40 @@ const IconSeparator = styled.div`
 
 const AcceptedFiles = ({
   fileNames,
+  renderAdditionalActions,
   onDeleteFile
 }: {
   fileNames: string[];
+  renderAdditionalActions?: (fileInfo: {
+    fileName: string;
+    index: number;
+    totalFiles: number;
+  }) => ReactNode;
   onDeleteFile: (fileName: string) => void;
-}) => {
-  return (
-    <FileList>
-      <p>File{fileNames.length > 1 && 's'} to upload:</p>
-      {fileNames.map((name, idx) => (
-        <AcceptedFile key={`${name}_${idx}`}>
-          <p>{name}</p>
-          <IconSeparator>
-            <IconButton
-              aria-label={`Delete ${name}`}
-              sx={{ padding: 0 }}
-              onClick={() => onDeleteFile(name)}
-            >
-              <BiTrash />
-            </IconButton>
-          </IconSeparator>
-        </AcceptedFile>
-      ))}
-    </FileList>
-  );
-};
+}) => (
+  <FileList>
+    <p>File{fileNames.length > 1 && 's'} to upload:</p>
+    {fileNames.map((fileName, index) => (
+      <AcceptedFile key={`${fileName}_${index}`}>
+        <p>{fileName}</p>
+        <IconSeparator>
+          {renderAdditionalActions?.({
+            fileName,
+            index,
+            totalFiles: fileNames.length
+          })}
+          <IconButton
+            aria-label={`Delete ${fileName}`}
+            sx={{ padding: 0 }}
+            onClick={() => onDeleteFile(fileName)}
+          >
+            <BiTrash />
+          </IconButton>
+        </IconSeparator>
+      </AcceptedFile>
+    ))}
+  </FileList>
+);
 
 const hasValidFileExtension = (file: File, validExtensions: Extension[]) => {
   const fileExtension = `.${file.name.split('.').pop()}`;
@@ -161,6 +175,7 @@ export const DragAndDropInput = ({
   id,
   multiple = false,
   name,
+  renderAdditionalFileActions,
   onDrop,
   validFileExtensions
 }: DragAndDropInputProps) => {
@@ -213,6 +228,7 @@ export const DragAndDropInput = ({
         <AcceptedFiles
           fileNames={acceptedFileNames}
           onDeleteFile={onDeleteFile}
+          renderAdditionalActions={renderAdditionalFileActions}
         />
       )}
       {!!rejectedFileErrors.length && !hideErrors && (