diff --git a/packages/compass-components/src/components/file-picker-dialog.spec.tsx b/packages/compass-components/src/components/file-picker-dialog.spec.tsx
index 8a957895d89..02942842d19 100644
--- a/packages/compass-components/src/components/file-picker-dialog.spec.tsx
+++ b/packages/compass-components/src/components/file-picker-dialog.spec.tsx
@@ -565,6 +565,26 @@ describe('FileInput', function () {
       expect(listener).to.been.calledOnceWith([]);
     });
 
+    it('calls the listener with an empty array if the dialog rejects', async function () {
+      const { fakeElectron, fakeWebUtils } = createFakeElectron();
+
+      const backend = createElectronFileInputBackend(
+        fakeElectron,
+        fakeWebUtils
+      )();
+      const listener = sinon.stub();
+      backend.onFilesChosen(listener);
+
+      fakeElectron.dialog.showOpenDialog.rejects(new Error('dialog failed'));
+      backend.openFileChooser({
+        mode: 'open',
+        multi: false,
+      });
+      expect(listener).to.not.have.been.called;
+      await tick();
+      expect(listener).to.been.calledOnceWith([]);
+    });
+
     it('handles autoOpen:true', async function () {
       const { fakeElectron, fakeWebUtils } = createFakeElectron();
       const backend = createElectronFileInputBackend(
diff --git a/packages/compass-components/src/components/file-picker-dialog.tsx b/packages/compass-components/src/components/file-picker-dialog.tsx
index 1cefeeb7272..1753353acba 100644
--- a/packages/compass-components/src/components/file-picker-dialog.tsx
+++ b/packages/compass-components/src/components/file-picker-dialog.tsx
@@ -300,7 +300,7 @@ export function createElectronFileInputBackend<ElectronWindow>(
             for (const listener of listeners) listener(files);
           })
           .catch(() => {
-            /* ignore */
+            for (const listener of listeners) listener([]);
           });
       },
       onFilesChosen(listener) {
diff --git a/packages/compass-crud/src/stores/crud-store.ts b/packages/compass-crud/src/stores/crud-store.ts
index 895f0e95350..ed67c138779 100644
--- a/packages/compass-crud/src/stores/crud-store.ts
+++ b/packages/compass-crud/src/stores/crud-store.ts
@@ -1266,10 +1266,12 @@ class CrudStoreImpl
    * Open an import file dialog from compass-import-export-plugin.
    * Emits a global app registry event the plugin listens to.
    */
-  openImportFileDialog() {
+  openImportFileDialog(
+    origin: 'empty-state' | 'crud-toolbar' = 'empty-state'
+  ) {
     this.connectionScopedAppRegistry.emit('open-import', {
       namespace: this.state.ns,
-      origin: 'empty-state',
+      origin,
     });
   }
 
diff --git a/packages/compass-import-export/src/components/import-modal.tsx b/packages/compass-import-export/src/components/import-modal.tsx
index 5321b28cc0d..e9f4d4db814 100644
--- a/packages/compass-import-export/src/components/import-modal.tsx
+++ b/packages/compass-import-export/src/components/import-modal.tsx
@@ -75,6 +75,7 @@ const dataTypesLinkStyles = css({
 
 type ImportModalProps = {
   isOpen: boolean;
+  openId: number;
   ns: string;
   startImport: () => void;
   cancelImport: () => void;
@@ -115,6 +116,7 @@ type ImportModalProps = {
 
 function ImportModal({
   isOpen,
+  openId,
   ns,
   startImport,
   cancelImport,
@@ -171,11 +173,12 @@ function ImportModal({
 
   if (isOpen && !fileName && errors.length === 0) {
     // Show the file input when we don't have a file to import yet.
+    // Use openId as key to force remounting when import is re-opened,
+    // ensuring autoOpen triggers the file dialog each time.
     return (
-      // Don't actually show it on the screen, just render it to trigger
-      // autoOpen
       <div style={{ display: 'none' }}>
         <ImportFileInput
+          key={openId}
           autoOpen
           onCancel={handleClose}
           fileName={fileName}
@@ -272,6 +275,7 @@ function ImportModal({
 const mapStateToProps = (state: RootImportState) => ({
   ns: state.import.namespace,
   isOpen: state.import.isOpen,
+  openId: state.import.openId,
   errors: state.import.firstErrors,
   fileType: state.import.fileType,
   fileName: state.import.fileName,
diff --git a/packages/compass-import-export/src/modules/import.spec.ts b/packages/compass-import-export/src/modules/import.spec.ts
index aca2d9d7a6f..b09aaadb4d3 100644
--- a/packages/compass-import-export/src/modules/import.spec.ts
+++ b/packages/compass-import-export/src/modules/import.spec.ts
@@ -1,6 +1,11 @@
 import { expect } from 'chai';
 import path from 'path';
-import { onStarted, openImport, selectImportFileName } from './import';
+import {
+  onStarted,
+  openImport,
+  selectImportFileName,
+  closeImport,
+} from './import';
 import type { ImportStore } from '../stores/import-store';
 import { ImportPlugin } from '../index';
 import { createPluginTestHelpers } from '@mongodb-js/testing-library-compass';
@@ -80,6 +85,50 @@ describe('import [module]', function () {
       );
       expect(mockStore.getState().import.isOpen).to.equal(true);
     });
+
+    it('increments openId each time import is opened', function () {
+      expect(mockStore.getState().import.openId).to.equal(0);
+
+      mockStore.dispatch(
+        openImport({
+          namespace: 'test.test',
+          origin: 'menu',
+          connectionId: 'TEST',
+        }) as any
+      );
+      expect(mockStore.getState().import.openId).to.equal(1);
+
+      mockStore.dispatch(closeImport());
+
+      mockStore.dispatch(
+        openImport({
+          namespace: 'test.test',
+          origin: 'menu',
+          connectionId: 'TEST',
+        }) as any
+      );
+      expect(mockStore.getState().import.openId).to.equal(2);
+    });
+
+    it('increments openId even when re-opened without closing first', function () {
+      mockStore.dispatch(
+        openImport({
+          namespace: 'test.test',
+          origin: 'menu',
+          connectionId: 'TEST',
+        }) as any
+      );
+      const firstOpenId = mockStore.getState().import.openId;
+
+      mockStore.dispatch(
+        openImport({
+          namespace: 'test.test',
+          origin: 'menu',
+          connectionId: 'TEST',
+        }) as any
+      );
+      expect(mockStore.getState().import.openId).to.equal(firstOpenId + 1);
+    });
   });
 
   describe('#selectImportFileName', function () {
diff --git a/packages/compass-import-export/src/modules/import.ts b/packages/compass-import-export/src/modules/import.ts
index cc4d2788af0..e3b5ed8910e 100644
--- a/packages/compass-import-export/src/modules/import.ts
+++ b/packages/compass-import-export/src/modules/import.ts
@@ -86,6 +86,7 @@ type FieldType = FieldFromJSON | FieldFromCSV;
 type ImportState = {
   isOpen: boolean;
   isInProgressMessageOpen: boolean;
+  openId: number;
   firstErrors: Error[];
   fileType: AcceptedFileType | '';
   fileName: string;
@@ -122,6 +123,7 @@ type ImportState = {
 export const INITIAL_STATE: ImportState = {
   isOpen: false,
   isInProgressMessageOpen: false,
+  openId: 0,
   firstErrors: [],
   fileName: '',
   errorLogFilePath: '',
@@ -1117,6 +1119,7 @@ export const importReducer: Reducer<ImportState> = (
   if (action.type === OPEN) {
     return {
       ...INITIAL_STATE,
+      openId: state.openId + 1,
       namespace: action.namespace,
       connectionId: action.connectionId,
       isOpen: true,