diff --git a/src/wp-admin/includes/ajax-actions.php b/src/wp-admin/includes/ajax-actions.php
index 7aa25cab4c..964aba357f 100644
--- a/src/wp-admin/includes/ajax-actions.php
+++ b/src/wp-admin/includes/ajax-actions.php
@@ -3970,20 +3970,47 @@ function wp_ajax_crop_image() {
 			/** This filter is documented in wp-admin/includes/class-custom-image-header.php */
 			$cropped = apply_filters( 'wp_create_file_in_uploads', $cropped, $attachment_id ); // For replication.
 
-			$parent_url = wp_get_attachment_url( $attachment_id );
-			$url        = str_replace( wp_basename( $parent_url ), wp_basename( $cropped ), $parent_url );
+			$parent_url      = wp_get_attachment_url( $attachment_id );
+			$parent_basename = wp_basename( $parent_url );
+			$url             = str_replace( $parent_basename, wp_basename( $cropped ), $parent_url );
 
 			$size       = wp_getimagesize( $cropped );
 			$image_type = ( $size ) ? $size['mime'] : 'image/jpeg';
 
+			// Get the original image's post to pre-populate the cropped image.
+			$original_attachment      = get_post( $attachment_id );
+			$sanitized_post_title     = sanitize_file_name( $original_attachment->post_title );
+			$use_original_title       = (
+				( '' !== trim( $original_attachment->post_title ) ) &&
+				/*
+				 * Check if the original image has a title other than the "filename" default,
+				 * meaning the image had a title when originally uploaded or its title was edited.
+				 */
+				( $parent_basename !== $sanitized_post_title ) &&
+				( pathinfo( $parent_basename, PATHINFO_FILENAME ) !== $sanitized_post_title )
+			);
+			$use_original_description = ( '' !== trim( $original_attachment->post_content ) );
+
 			$object = array(
-				'post_title'     => wp_basename( $cropped ),
-				'post_content'   => $url,
+				'post_title'     => $use_original_title ? $original_attachment->post_title : wp_basename( $cropped ),
+				'post_content'   => $use_original_description ? $original_attachment->post_content : $url,
 				'post_mime_type' => $image_type,
 				'guid'           => $url,
 				'context'        => $context,
 			);
 
+			// Copy the image caption attribute (post_excerpt field) from the original image.
+			if ( '' !== trim( $original_attachment->post_excerpt ) ) {
+				$object['post_excerpt'] = $original_attachment->post_excerpt;
+			}
+
+			// Copy the image alt text attribute from the original image.
+			if ( '' !== trim( $original_attachment->_wp_attachment_image_alt ) ) {
+				$object['meta_input'] = array(
+					'_wp_attachment_image_alt' => wp_slash( $original_attachment->_wp_attachment_image_alt ),
+				);
+			}
+
 			$attachment_id = wp_insert_attachment( $object, $cropped );
 			$metadata      = wp_generate_attachment_metadata( $attachment_id, $cropped );
 
diff --git a/tests/phpunit/tests/ajax/wpAjaxCropImage.php b/tests/phpunit/tests/ajax/wpAjaxCropImage.php
new file mode 100644
index 0000000000..94e66ffe69
--- /dev/null
+++ b/tests/phpunit/tests/ajax/wpAjaxCropImage.php
@@ -0,0 +1,222 @@
+<?php
+
+/**
+ * Admin Ajax functions to be tested.
+ */
+require_once ABSPATH . 'wp-admin/includes/ajax-actions.php';
+require_once ABSPATH . 'wp-admin/includes/class-wp-filesystem-base.php';
+require_once ABSPATH . 'wp-admin/includes/class-wp-filesystem-direct.php';
+
+/**
+ * Class for testing ajax crop image functionality.
+ *
+ * @group ajax
+ * @covers ::wp_ajax_crop_image
+ */
+class Tests_Ajax_WpAjaxCropImage extends WP_Ajax_UnitTestCase {
+
+	/**
+	 * @var WP_Post|null
+	 */
+	private $attachment;
+
+	/**
+	 * @var WP_Post|null
+	 */
+	private $cropped_attachment;
+
+	public function set_up() {
+		parent::set_up();
+
+		// Become an administrator.
+		$this->_setRole( 'administrator' );
+	}
+
+	public function tear_down() {
+		if ( $this->attachment instanceof WP_Post ) {
+			wp_delete_attachment( $this->attachment->ID, true );
+		}
+
+		if ( $this->cropped_attachment instanceof WP_Post ) {
+			wp_delete_attachment( $this->cropped_attachment->ID, true );
+		}
+		$this->attachment         = null;
+		$this->cropped_attachment = null;
+
+		parent::tear_down();
+	}
+
+	/**
+	 * Tests that attachment properties are copied over to the cropped image.
+	 *
+	 * @ticket 37750
+	 */
+	public function test_it_copies_metadata_from_original_image() {
+		$this->attachment = $this->make_attachment( true );
+		$this->prepare_post( $this->attachment );
+
+		// Make the request.
+		try {
+			$this->_handleAjax( 'crop-image' );
+		} catch ( WPAjaxDieContinueException $e ) {
+		}
+
+		$response = json_decode( $this->_last_response, true );
+		$this->validate_response( $response );
+
+		$this->cropped_attachment = get_post( $response['data']['id'] );
+		$this->assertInstanceOf( WP_Post::class, $this->cropped_attachment, 'get_post function must return an instance of WP_Post class' );
+		$this->assertNotEmpty( $this->attachment->post_title, 'post_title value must not be empty for testing purposes' );
+		$this->assertNotEmpty( $this->cropped_attachment->post_title, 'post_title value must not be empty for testing purposes' );
+		$this->assertSame( $this->attachment->post_title, $this->cropped_attachment->post_title, 'post_title value should be copied over to the cropped attachment' );
+		$this->assertSame( $this->attachment->post_content, $this->cropped_attachment->post_content, 'post_content value should be copied over to the cropped attachment' );
+		$this->assertSame( $this->attachment->post_excerpt, $this->cropped_attachment->post_excerpt, 'post_excerpt value should be copied over to the cropped attachment' );
+		$this->assertSame( $this->attachment->_wp_attachment_image_alt, $this->cropped_attachment->_wp_attachment_image_alt, '_wp_attachment_image_alt value should be copied over to the cropped attachment' );
+	}
+
+	/**
+	 * Tests that post_title gets populated if it wasn't modified.
+	 *
+	 * @ticket 37750
+	 */
+	public function test_it_populates_title_if_title_was_not_modified() {
+
+		$this->attachment = $this->make_attachment( true );
+		$filename         = $this->get_attachment_filename( $this->attachment );
+		$this->attachment = get_post(
+			wp_update_post(
+				array(
+					'ID'         => $this->attachment->ID,
+					'post_title' => $filename,
+				)
+			)
+		);
+
+		$this->prepare_post( $this->attachment );
+
+		// Make the request.
+		try {
+			$this->_handleAjax( 'crop-image' );
+		} catch ( WPAjaxDieContinueException $e ) {
+		}
+
+		$response = json_decode( $this->_last_response, true );
+		$this->validate_response( $response );
+
+		$this->cropped_attachment = get_post( $response['data']['id'] );
+		$this->assertInstanceOf( WP_Post::class, $this->cropped_attachment, 'get_post function must return an instance of WP_Post class' );
+		$this->assertStringStartsWith( 'cropped-', $this->cropped_attachment->post_title, 'post_title attribute should start with "cropped-" prefix, i.e. it has to be populated' );
+	}
+
+	/**
+	 * Tests that attachment properties get populated if they are not defined (but specific logic depends on the actual property).
+	 *
+	 * @ticket 37750
+	 */
+	public function test_it_doesnt_generate_new_metadata_if_metadata_is_empty() {
+		$this->attachment = $this->make_attachment( false );
+		$this->prepare_post( $this->attachment );
+
+		// Make the request.
+		try {
+			$this->_handleAjax( 'crop-image' );
+		} catch ( WPAjaxDieContinueException $e ) {
+		}
+
+		$response = json_decode( $this->_last_response, true );
+		$this->validate_response( $response );
+
+		$this->cropped_attachment = get_post( $response['data']['id'] );
+		$this->assertInstanceOf( WP_Post::class, $this->cropped_attachment, 'get_post function must return an instance of WP_Post class' );
+		$this->assertEmpty( $this->attachment->post_title, 'post_title value must be empty for testing purposes' );
+		$this->assertNotEmpty( $this->cropped_attachment->post_title, 'post_title value must be auto-generated if it\'s empty in the original attachment' );
+		$this->assertSame( $this->get_attachment_filename( $this->cropped_attachment ), $this->cropped_attachment->post_title, 'post_title attribute should contain filename of the cropped image' );
+		$this->assertStringStartsWith( 'cropped-', $this->cropped_attachment->post_title, 'post_title attribute should start with "cropped-" prefix, i.e. it has to be populated' );
+		$this->assertStringStartsWith( 'http', $this->cropped_attachment->post_content, 'post_content value should contain an URL if it\'s empty in the original attachment' );
+		$this->assertEmpty( $this->cropped_attachment->post_excerpt, 'post_excerpt value must be empty if it\'s empty in the original attachment' );
+		$this->assertEmpty( $this->cropped_attachment->_wp_attachment_image_alt, '_wp_attachment_image_alt value must be empty if it\'s empty in the original attachment' );
+	}
+
+	/**
+	 * Creates an attachment.
+	 *
+	 * @return WP_Post
+	 */
+	private function make_attachment( $with_metadata = true ) {
+		$uniq_id = uniqid( 'crop-image-ajax-action-test-' );
+
+		$test_file        = DIR_TESTDATA . '/images/test-image.jpg';
+		$upload_directory = wp_upload_dir();
+		$uploaded_file    = $upload_directory['path'] . '/' . $uniq_id . '.jpg';
+		$filesystem       = new WP_Filesystem_Direct( true );
+		$filesystem->copy( $test_file, $uploaded_file );
+
+		$attachment_data = array(
+			'file' => $uploaded_file,
+			'type' => 'image/jpg',
+			'url'  => 'http://localhost/foo.jpg',
+		);
+
+		$attachment_id = $this->_make_attachment( $attachment_data );
+		$post_data     = array(
+			'ID'           => $attachment_id,
+			'post_title'   => $with_metadata ? 'Title ' . $uniq_id : '',
+			'post_content' => $with_metadata ? 'Description ' . $uniq_id : '',
+			'context'      => 'custom-logo',
+			'post_excerpt' => $with_metadata ? 'Caption ' . $uniq_id : '',
+		);
+
+		// Update the post because _make_attachment method doesn't support these arguments.
+		wp_update_post( $post_data );
+
+		if ( $with_metadata ) {
+			update_post_meta( $attachment_id, '_wp_attachment_image_alt', wp_slash( 'Alt ' . $uniq_id ) );
+		}
+
+		return get_post( $attachment_id );
+	}
+
+	/**
+	 * @param array $response Response to validate.
+	 */
+	private function validate_response( $response ) {
+		$this->assertArrayHasKey( 'success', $response, 'Response array must contain "success" key.' );
+		$this->assertArrayHasKey( 'data', $response, 'Response array must contain "data" key.' );
+		$this->assertNotEmpty( $response['data']['id'], 'Response array must contain "ID" value of the post entity.' );
+	}
+
+	/**
+	 * Prepares $_POST for crop-image ajax action.
+	 *
+	 * @param WP_Post $attachment
+	 */
+	private function prepare_post( WP_Post $attachment ) {
+		$_POST = array(
+			'wp_customize' => 'on',
+			'nonce'        => wp_create_nonce( 'image_editor-' . $attachment->ID ),
+			'id'           => $attachment->ID,
+			'context'      => 'custom_logo',
+			'cropDetails'  =>
+				array(
+					'x1'         => '0',
+					'y1'         => '0',
+					'x2'         => '100',
+					'y2'         => '100',
+					'width'      => '100',
+					'height'     => '100',
+					'dst_width'  => '100',
+					'dst_height' => '100',
+				),
+			'action'       => 'crop-image',
+		);
+	}
+
+	/**
+	 * @param WP_Post $attachment
+	 *
+	 * @return string
+	 */
+	private function get_attachment_filename( WP_Post $attachment ) {
+		return wp_basename( wp_get_attachment_url( $attachment->ID ) );
+	}
+}