diff --git a/apps/cli/lib/import-export/import/importers/importer.ts b/apps/cli/lib/import-export/import/importers/importer.ts
index be9dc6e86d..6b8ae3b809 100644
--- a/apps/cli/lib/import-export/import/importers/importer.ts
+++ b/apps/cli/lib/import-export/import/importers/importer.ts
@@ -4,6 +4,7 @@ import { createInterface } from 'readline';
 import { DEFAULT_PHP_VERSION } from '@studio/common/constants';
 import { generateBackupFilename } from '@studio/common/lib/generate-backup-filename';
 import { ImportEvents } from '@studio/common/lib/import-export-events';
+import { isErrnoException } from '@studio/common/lib/is-errno-exception';
 import { serializePlugins } from '@studio/common/lib/serialize-plugins';
 import { type SupportedPHPVersion } from '@studio/common/types/php-versions';
 import { __, sprintf } from '@wordpress/i18n';
@@ -28,6 +29,34 @@ export interface Importer extends ImportExportEventEmitter {
 	import( site: SiteData ): Promise< ImporterResult >;
 }
 
+// Recovers from EEXIST/ENOTDIR by removing a non-directory blocker on the path.
+export async function ensureDir( dir: string ): Promise< void > {
+	try {
+		await fs.promises.mkdir( dir, { recursive: true } );
+	} catch ( error ) {
+		if ( ! isErrnoException( error ) || ( error.code !== 'EEXIST' && error.code !== 'ENOTDIR' ) ) {
+			throw error;
+		}
+		const parent = path.dirname( dir );
+		if ( parent === dir ) {
+			throw error;
+		}
+		await ensureDir( parent );
+		try {
+			const stat = await fs.promises.stat( dir );
+			if ( ! stat.isDirectory() ) {
+				await trash( dir );
+				console.warn( `ensureDir: moved non-directory blocker at ${ dir } to trash` );
+			}
+		} catch ( e ) {
+			if ( ! isErrnoException( e ) || e.code !== 'ENOENT' ) {
+				throw e;
+			}
+		}
+		await fs.promises.mkdir( dir, { recursive: true } );
+	}
+}
+
 abstract class BaseImporter extends ImportExportEventEmitter implements Importer {
 	protected meta?: MetaFileData;
 
@@ -236,7 +265,7 @@ abstract class BaseBackupImporter extends BaseImporter {
 				);
 
 				const destPath = path.join( wpContentDestDir, relativePath );
-				await fs.promises.mkdir( path.dirname( destPath ), { recursive: true } );
+				await ensureDir( path.dirname( destPath ) );
 				await fs.promises.copyFile( file, destPath );
 
 				processedItems++;
diff --git a/apps/cli/lib/import-export/import/importers/tests/importer.test.ts b/apps/cli/lib/import-export/import/importers/tests/importer.test.ts
new file mode 100644
index 0000000000..816e8c0571
--- /dev/null
+++ b/apps/cli/lib/import-export/import/importers/tests/importer.test.ts
@@ -0,0 +1,55 @@
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+import { describe, it, expect, beforeEach, afterEach } from 'vitest';
+import { ensureDir } from '../importer';
+
+describe( 'ensureDir', () => {
+	let tmpDir: string;
+
+	beforeEach( () => {
+		tmpDir = fs.mkdtempSync( path.join( os.tmpdir(), 'studio-ensure-dir-' ) );
+	} );
+
+	afterEach( () => {
+		fs.rmSync( tmpDir, { recursive: true, force: true } );
+	} );
+
+	it( 'creates a directory that does not exist', async () => {
+		const target = path.join( tmpDir, 'a', 'b', 'c' );
+		await ensureDir( target );
+		expect( fs.lstatSync( target ).isDirectory() ).toBe( true );
+	} );
+
+	it( 'is a no-op when the directory already exists', async () => {
+		const target = path.join( tmpDir, 'existing' );
+		fs.mkdirSync( target );
+		await expect( ensureDir( target ) ).resolves.toBeUndefined();
+		expect( fs.lstatSync( target ).isDirectory() ).toBe( true );
+	} );
+
+	it( 'replaces a non-directory file blocking the target path', async () => {
+		const plugins = path.join( tmpDir, 'wp-content', 'plugins' );
+		fs.mkdirSync( plugins, { recursive: true } );
+		const blocker = path.join( plugins, 'akismet' );
+		fs.writeFileSync( blocker, '/managed/akismet' );
+		expect( fs.lstatSync( blocker ).isFile() ).toBe( true );
+
+		await ensureDir( blocker );
+
+		expect( fs.lstatSync( blocker ).isDirectory() ).toBe( true );
+	} );
+
+	it( 'replaces a non-directory file blocking an ancestor of the target path', async () => {
+		const plugins = path.join( tmpDir, 'wp-content', 'plugins' );
+		fs.mkdirSync( plugins, { recursive: true } );
+		const blocker = path.join( plugins, 'akismet' );
+		fs.writeFileSync( blocker, '/managed/akismet' );
+
+		const deeper = path.join( blocker, '_inc' );
+		await ensureDir( deeper );
+
+		expect( fs.lstatSync( blocker ).isDirectory() ).toBe( true );
+		expect( fs.lstatSync( deeper ).isDirectory() ).toBe( true );
+	} );
+} );