diff --git a/cli/lib/archive.ts b/cli/lib/archive.ts
index 31089ec91a..1c249af87b 100644
--- a/cli/lib/archive.ts
+++ b/cli/lib/archive.ts
@@ -1,7 +1,8 @@
 import fs from 'fs';
+import fsPromises from 'fs/promises';
 import path from 'path';
 import { __ } from '@wordpress/i18n';
-import archiver, { EntryData } from 'archiver';
+import archiver from 'archiver';
 import { LoggerError } from 'cli/logger';
 
 const ZIP_COMPRESSION_LEVEL = 9;
@@ -10,6 +11,11 @@ export async function createArchive(
 	siteFolder: string,
 	archivePath: string
 ): Promise< archiver.Archiver > {
+	const wpContentFolder = path.join( siteFolder, 'wp-content' );
+	const directoryContents = await fsPromises.readdir( wpContentFolder, {
+		recursive: true,
+	} );
+
 	return new Promise( ( resolve, reject ) => {
 		const output = fs.createWriteStream( archivePath );
 		const archive = archiver( 'zip', {
@@ -24,16 +30,19 @@ export async function createArchive(
 		} );
 
 		archive.pipe( output );
-		archive.directory(
-			path.join( siteFolder, 'wp-content' ),
-			'wp-content',
-			( entry: EntryData ) => {
-				if ( entry.name.includes( '.git' ) || entry.name.includes( 'node_modules' ) ) {
-					return false;
-				}
-				return entry;
+
+		for ( const entryPath of directoryContents ) {
+			if ( entryPath.includes( '.git' ) || entryPath.includes( 'node_modules' ) ) {
+				continue;
+			}
+
+			const absolutePath = path.join( wpContentFolder, entryPath );
+			const filePath = getRealFilePathIfExists( absolutePath );
+			const archivePath = path.relative( siteFolder, absolutePath );
+			if ( filePath ) {
+				archive.file( filePath, { name: archivePath } );
 			}
-		);
+		}
 
 		const wpConfigPath = path.join( siteFolder, 'wp-config.php' );
 		if ( fs.existsSync( wpConfigPath ) ) {
@@ -55,3 +64,21 @@ export async function cleanup( archivePath: string ): Promise< void > {
 		}, 0 );
 	} );
 }
+
+function getRealFilePathIfExists( absolutePath: string ): string | null {
+	const stat = fs.lstatSync( absolutePath );
+	if ( stat.isFile() ) {
+		return absolutePath;
+	}
+
+	if ( stat.isSymbolicLink() ) {
+		try {
+			return fs.realpathSync( absolutePath );
+		} catch ( error ) {
+			// If there's an error resolving the symlink, return null
+			return null;
+		}
+	}
+	// Ignore directories
+	return null;
+}
diff --git a/cli/lib/tests/archive.test.ts b/cli/lib/tests/archive.test.ts
index bb59ac32d0..0fc98842ba 100644
--- a/cli/lib/tests/archive.test.ts
+++ b/cli/lib/tests/archive.test.ts
@@ -1,9 +1,11 @@
 import fs from 'fs';
+import fsPromises from 'fs/promises';
 import path from 'path';
 import archiver from 'archiver';
 import { createArchive, cleanup } from 'cli/lib/archive';
 
 jest.mock( 'fs' );
+jest.mock( 'fs/promises' );
 jest.mock( 'path' );
 jest.mock( 'archiver' );
 
@@ -12,6 +14,12 @@ describe( 'Archive Module', () => {
 	const mockArchivePath = '/mock/archive.zip';
 	const mockWpContentPath = '/mock/site/folder/wp-content';
 	const mockWpConfigPath = '/mock/site/folder/wp-config.php';
+	const mockDirectoryContents = [
+		'/mock/site/wp-content/plugins/my-plugin',
+		'/mock/site/wp-content/plugins/my-plugin/my-plugin.php',
+		'/mock/site/wp-content/plugins/my-symlinked-plugin.php',
+	];
+	const mockSymLinkedFilePath = '/mock/temp/symlinked-file.txt';
 
 	const mockArchiver = {
 		pipe: jest.fn(),
@@ -28,8 +36,12 @@ describe( 'Archive Module', () => {
 	beforeEach( () => {
 		jest.clearAllMocks();
 		( archiver as unknown as jest.Mock ).mockReturnValue( mockArchiver );
-		( fs.createWriteStream as jest.Mock ).mockReturnValue( mockWriteStream );
-		( path.join as jest.Mock ).mockImplementation( ( ...args ) => args.join( '/' ) );
+		( fs.createWriteStream as unknown as jest.Mock ).mockReturnValue( mockWriteStream );
+		( fsPromises.readdir as unknown as jest.Mock ).mockResolvedValue( mockDirectoryContents );
+		( path.join as unknown as jest.Mock ).mockImplementation( ( ...args ) => args.join( '/' ) );
+		( fs.lstatSync as unknown as jest.Mock ).mockReturnValue( {
+			isFile: () => true,
+		} );
 	} );
 
 	describe( 'createArchive', () => {
@@ -50,19 +62,38 @@ describe( 'Archive Module', () => {
 			expect( fs.createWriteStream ).toHaveBeenCalledWith( mockArchivePath );
 			expect( archiver ).toHaveBeenCalledWith( 'zip', { zlib: { level: 9 } } );
 			expect( mockArchiver.pipe ).toHaveBeenCalledWith( mockWriteStream );
+			expect( fsPromises.readdir ).toHaveBeenCalledWith( mockWpContentPath, {
+				recursive: true,
+			} );
 			expect( path.join ).toHaveBeenCalledWith( mockSiteFolder, 'wp-content' );
-			expect( mockArchiver.directory ).toHaveBeenCalledWith(
-				mockWpContentPath,
-				'wp-content',
-				expect.any( Function )
-			);
-			expect( path.join ).toHaveBeenCalledWith( mockSiteFolder, 'wp-config.php' );
-			expect( fs.existsSync ).toHaveBeenCalledWith( mockWpConfigPath );
-			expect( mockArchiver.file ).not.toHaveBeenCalled();
+			expect( mockArchiver.file ).toHaveBeenCalled();
 			expect( mockArchiver.finalize ).toHaveBeenCalled();
 			expect( result ).toBe( mockArchiver );
 		} );
 
+		it( 'should handle symbolic links correctly', async () => {
+			( fs.realpathSync as unknown as jest.Mock ).mockReturnValue( mockSymLinkedFilePath );
+			( fs.lstatSync as unknown as jest.Mock ).mockReturnValue( {
+				isFile: () => false,
+				isSymbolicLink: () => true,
+			} );
+
+			mockWriteStream.on.mockImplementation( ( event, callback ) => {
+				if ( event === 'close' ) {
+					setTimeout( () => callback(), 0 );
+				}
+				return mockWriteStream;
+			} );
+
+			mockArchiver.on.mockImplementation( () => mockArchiver );
+
+			await createArchive( mockSiteFolder, mockArchivePath );
+
+			expect( fs.realpathSync ).toHaveBeenCalled();
+			expect( fs.lstatSync ).toHaveBeenCalled();
+			expect( mockArchiver.file ).toHaveBeenCalled();
+		} );
+
 		it( 'should include wp-config.php if it exists', async () => {
 			( fs.existsSync as jest.Mock ).mockReturnValue( true );