diff --git a/CHANGELOG.md b/CHANGELOG.md
index 745fa7c..b4a3dbb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,7 +1,24 @@
+
 # Changelog
 
 All notable changes to `WP Block Converter` will be documented in this file.
 
+## 1.5.0
+
+### Added
+
+- Add collection of attachments that are created during the conversion process.
+  Two methods now exist on the converter to help:
+  - `get_created_attachment_ids()` - Returns the attachment IDs that were created.
+  - `assign_parent_to_attachments()` - Assigns a parent post to all attachments.
+
+### Changed
+
+- Nested images are now properly sideloaded and converted to image blocks where
+  appropriate. For example, an image inside a figure tag will now be converted
+  to an image block. An image within a paragraph tag will be sideloaded but
+  won't be converted to an image block.
+
 ## 1.4.0
 
 - Drops support for PHP 8.0.
diff --git a/README.md b/README.md
index eaba953..dd28bd4 100644
--- a/README.md
+++ b/README.md
@@ -1,7 +1,6 @@
 # WP Block Converter
 
-[![Coding Standards](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/coding-standards.yml/badge.svg)](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/coding-standards.yml)
-[![Testing Suite](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/unit-test.yml/badge.svg)](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/unit-test.yml)
+[![Testing Suite](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/all-pr-tests.yml/badge.svg)](https://github.com/alleyinteractive/wp-block-converter/actions/workflows/all-pr-tests.yml)
 
 Convert HTML into Gutenberg Blocks with PHP
 
@@ -13,9 +12,9 @@ You can install the package via Composer:
 composer require alleyinteractive/wp-block-converter
 ```
 
-This project is built to be used in a WordPress environment, so it is
-recommended to use this package in a WordPress plugin or theme. Using it in
-isolation is not supported at this time.
+This project is built to be used in a WordPress environment, so it is recommended to use this
+package in a WordPress plugin or theme. Using it in isolation is not supported at this time. This
+package does not use any NPM library such as `@wordpress/blocks` to convert HTML to blocks.
 
 ## Usage
 
@@ -26,7 +25,7 @@ use Alley\WP\Block_Converter\Block_Converter;
 
 $converter = new Block_Converter( '<p>Some HTML</p>' );
 
-$blocks = $converter->convert();
+$blocks = $converter->convert(); // Returns a string of converted blocks.
 ```
 
 ### Filtering the Blocks
@@ -61,6 +60,24 @@ add_filter( 'wp_block_converter_document_html', function( string $blocks, \DOMNo
 }, 10, 2 );
 ```
 
+### Attachment Parents
+
+When converting HTML to blocks, you may need to attach the images that were
+sideloaded to a post parent. After the HTML is converted to blocks, you can get
+the attachment IDs that were created or simply attach them to a post.
+
+```php
+$converter = new Block_Converter( '<p>Some HTML <img src="https://example.org/" /></p>' );
+$blocks = $converter->convert();
+
+// Get the attachment IDs that were created.
+$attachment_ids = $converter->get_created_attachment_ids();
+
+// Attach the images to a post.
+$parent_id = 123;
+$converter->assign_parent_to_attachments( $parent_id );
+```
+
 ### Extending the Converter with Macros
 
 You can extend the converter with macros to add custom tags that are not yet
diff --git a/src/class-block-converter.php b/src/class-block-converter.php
index 37ad774..bb2ca84 100644
--- a/src/class-block-converter.php
+++ b/src/class-block-converter.php
@@ -13,21 +13,32 @@
 use DOMNode;
 use Exception;
 use Mantle\Support\Traits\Macroable;
+use RuntimeException;
+use Throwable;
 
 /**
  * Converts a DOMDocument to Gutenberg block HTML.
+ *
+ * Mirrors the `htmlToBlocks()`/`rawHandler()` from the `@wordpress/blocks` package.
+ *
+ * @todo Improve logging to not silently fail when importing images.
  */
 class Block_Converter {
-	use Macroable {
+	use Concerns\Listens_For_Attachments, Macroable {
 		__call as macro_call;
 	}
 
 	/**
 	 * Setup the class.
 	 *
+	 * @throws RuntimeException If WordPress is not loaded.
+	 *
 	 * @param string $html The HTML to parse.
 	 */
 	public function __construct( public string $html ) {
+		if ( ! function_exists( 'do_action' ) ) {
+			throw new RuntimeException( 'WordPress must be loaded to use the Block_Converter class.' );
+		}
 	}
 
 	/**
@@ -36,6 +47,8 @@ public function __construct( public string $html ) {
 	 * @return string The HTML.
 	 */
 	public function convert(): string {
+		$this->listen_for_attachment_creation();
+
 		// Get tags from the html.
 		$content = static::get_node_tag_from_html( $this->html );
 
@@ -51,24 +64,8 @@ public function convert(): string {
 				continue;
 			}
 
-			/**
-			 * Hook to allow output customizations.
-			 *
-			 * @since 1.0.0
-			 *
-			 * @param Block|null $block The generated block object.
-			 * @param DOMNode   $node  The node being converted.
-			 */
-			$tag_block = apply_filters( 'wp_block_converter_block', $this->{$node->nodeName}( $node ), $node );
-
-			// Bail early if is empty.
-			if ( empty( $tag_block ) ) {
-				continue;
-			}
-
 			// Merge the block into the HTML collection.
-
-			$html[] = $this->minify_block( (string) $tag_block );
+			$html[] = $this->minify_block( (string) $this->convert_node( $node ) );
 		}
 
 		$html = implode( "\n\n", $html );
@@ -84,7 +81,103 @@ public function convert(): string {
 		 * @param string        $html    HTML converted into Gutenberg blocks.
 		 * @param DOMNodeList $content The original DOMNodeList.
 		 */
-		return trim( (string) apply_filters( 'wp_block_converter_document_html', $html, $content ) );
+		$html = trim( (string) apply_filters( 'wp_block_converter_document_html', $html, $content ) );
+
+		$this->detach_attachment_creation_listener();
+
+		return $html;
+	}
+
+	/**
+	 * Convert a node to a block.
+	 *
+	 * @param DOMNode $node The node to convert.
+	 * @return Block|null
+	 */
+	protected function convert_node( DOMNode $node ): ?Block {
+		if ( '#text' === $node->nodeName ) {
+			return null;
+		}
+
+		/**
+		 * Hook to allow output customizations.
+		 *
+		 * @since 1.0.0
+		 *
+		 * @param Block|null $block The generated block object.
+		 * @param DOMNode   $node  The node being converted.
+		 */
+		$block = apply_filters( 'wp_block_converter_block', $this->{$node->nodeName}( $node ), $node );
+
+		if ( ! $block || ! $block instanceof Block ) {
+			return null;
+		}
+
+		return $block;
+	}
+
+	/**
+	 * Sideload any child images of a DOMNode and replace the src with the new URL.
+	 *
+	 * @param DOMNode $node The node.
+	 * @return DOMNode
+	 */
+	protected function sideload_child_images( DOMNode $node ): void {
+		$children = $node->childNodes;
+
+		if ( ! $children->length ) {
+			return;
+		}
+
+		foreach ( $children as $child_node ) {
+			// Skip if the node is not an image or is not an instance of DOMElement.
+			if ( 'img' !== $child_node->nodeName || ! $child_node instanceof DOMElement ) {
+				// Recursively sideload images in child nodes.
+				if ( $child_node->hasChildNodes() ) {
+					$this->sideload_child_images( $child_node );
+				}
+
+				continue;
+			}
+
+			$src = $child_node->getAttribute( 'src' );
+
+			if ( empty( $src ) ) {
+				continue;
+			}
+
+			try {
+				$previous_src = $src;
+				$src          = $this->upload_image( $src, $child_node->getAttribute( 'alt' ) );
+
+				if ( $src ) {
+					$child_node->setAttribute( 'src', $src );
+
+					// Remove any srcset attributes.
+					if ( $child_node->hasAttribute( 'srcset' ) ) {
+						$child_node->removeAttribute( 'srcset' );
+					}
+
+					// Update the parent node with the new link if the parent
+					// node is an anchor.
+					if ( 'a' === $node->nodeName && $previous_src === $node->getAttribute( 'href' ) ) {
+						$node->setAttribute( 'href', $src );
+					}
+
+					/**
+					 * Fires after a child image has been sideloaded.
+					 *
+					 * @since 1.5.0
+					 *
+					 * @param string  $src        The image source URL.
+					 * @param DOMNode $child_node The child node.
+					 */
+					do_action( 'wp_block_converter_sideloaded_image', $src, $child_node );
+				}
+			} catch ( Throwable ) { // phpcs:ignore Squiz.Commenting.EmptyCatchComment.Missing, Generic.CodeAnalysis.EmptyStatement.DetectedCatch
+				// Do nothing.
+			}
+		}
 	}
 
 	/**
@@ -106,6 +199,7 @@ public function __call( $name, $arguments ): ?Block {
 			'blockquote' => $this->blockquote( $arguments[0] ),
 			'h1', 'h2', 'h3', 'h4', 'h5', 'h6' => $this->h( $arguments[0] ),
 			'p', 'a', 'abbr', 'b', 'code', 'em', 'i', 'strong', 'sub', 'sup', 'span', 'u' => $this->p( $arguments[0] ),
+			'figure' => $this->figure( $arguments[0] ),
 			'br', 'cite', 'source' => null,
 			'hr' => $this->separator(),
 			default => $this->html( $arguments[0] ),
@@ -201,8 +295,16 @@ protected function blockquote( DOMNode $node ): ?Block {
 	 * @return Block|null
 	 */
 	protected function p( DOMNode $node ): ?Block {
+		if ( $this->is_anchor_wrapped_image( $node ) ) {
+			return $this->img( $node );
+		}
+
+		$this->sideload_child_images( $node );
+
 		$content = static::get_node_html( $node );
 
+		// TODO: Account for Twitter/Facebook embeds being inline links in
+		// content and not full embeds.
 		if ( ! empty( filter_var( $node->textContent, FILTER_VALIDATE_URL ) ) ) {
 			if ( \str_contains( $node->textContent, '//x.com' ) || \str_contains( $node->textContent, '//www.x.com' ) ) {
 				$node->textContent = str_replace( 'x.com', 'twitter.com', $node->textContent );
@@ -234,6 +336,85 @@ protected function p( DOMNode $node ): ?Block {
 		);
 	}
 
+	/**
+	 * Create figure blocks.
+	 *
+	 * This method only supports converting a <figure> block that has either a
+	 * <img>, <a> or <figcaption> child. If the <figure> block has other children
+	 * the block will be converted to a HTML block.
+	 *
+	 * @param DOMNode $node The node.
+	 * @return Block|null
+	 */
+	public function figure( DOMNode $node ): ?Block {
+		if ( $this->is_supported_figure( $node ) ) {
+			$this->sideload_child_images( $node );
+
+			// Ensure it has the "wp-block-image" class.
+			if ( $node instanceof DOMElement ) {
+				$node->setAttribute( 'class', 'wp-block-image' );
+			}
+
+			return new Block(
+				block_name: 'image',
+				content: static::get_node_html( $node ),
+			);
+		}
+
+		return $this->html( $node );
+	}
+
+	/**
+	 * Check if the figure node is supported for conversion.
+	 *
+	 * @param DOMNode $node The node.
+	 * @return bool
+	 */
+	protected function is_supported_figure( DOMNode $node ): bool {
+		$children = $node->childNodes;
+
+		if ( ! $children->length ) {
+			return false;
+		}
+
+		if ( $children->length > 2 ) {
+			return false;
+		}
+
+		if ( 2 === $children->length ) {
+			if ( 'figcaption' !== $children->item( 1 )->nodeName ) {
+				return false;
+			}
+		}
+
+		// Check if the first child is an <img> or an <a> with an <img> child.
+		if ( 'img' === $children->item( 0 )->nodeName || $this->is_anchor_wrapped_image( $children->item( 0 ) ) ) {
+			return true;
+		}
+
+		return false;
+	}
+
+	/**
+	 * Check if the figure node is an anchor wrapped image.
+	 *
+	 * @param DOMNode $node The node.
+	 * @return bool
+	 */
+	protected function is_anchor_wrapped_image( DOMNode $node ): bool {
+		$children = $node->childNodes;
+
+		if ( ! $children->length ) {
+			return false;
+		}
+
+		if ( 1 === $children->length && 'img' === $children->item( 0 )->nodeName ) {
+			return true;
+		}
+
+		return false;
+	}
+
 	/**
 	 * Create ul blocks.
 	 *
@@ -241,6 +422,8 @@ protected function p( DOMNode $node ): ?Block {
 	 * @return Block
 	 */
 	protected function ul( DOMNode $node ): Block {
+		$this->sideload_child_images( $node );
+
 		return new Block(
 			block_name: 'list',
 			content: static::get_node_html( $node ),
@@ -248,7 +431,12 @@ protected function ul( DOMNode $node ): Block {
 	}
 
 	/**
-	 * Create img blocks.
+	 * Create img block.
+	 *
+	 * Supports being passed a element that is a <img> or a parent element that
+	 * contains an <img>. If it is passed a parent element that contains an
+	 * <img> tag, the resulting block will preserve the parent element and wrap
+	 * it in a <figure> tag.
 	 *
 	 * @param DOMElement|DOMNode $element The node.
 	 * @return Block|null
@@ -258,16 +446,36 @@ protected function img( DOMElement|DOMNode $element ): ?Block {
 			return null;
 		}
 
-		$image_src = $element->getAttribute( 'data-srcset' );
-		$alt       = $element->getAttribute( 'alt' );
+		// If the element passed isn't an <img> attempt to find it from the children.
+		if ( 'img' !== $element->nodeName ) {
+			$image_node = $element->getElementsByTagName( 'img' )->item( 0 );
 
-		if ( empty( $image_src ) && ! empty( $element->getAttribute( 'src' ) ) ) {
-			$image_src = $element->getAttribute( 'src' );
+			// Bail early if the image node is not found.
+			if ( ! $image_node || ! $image_node instanceof DOMElement ) {
+				return null;
+			}
+		} else {
+			$image_node = $element;
+		}
+
+		$image_src = $image_node->getAttribute( 'data-srcset' );
+		$alt       = $image_node->getAttribute( 'alt' );
+
+		if ( empty( $image_src ) && ! empty( $image_node->getAttribute( 'src' ) ) ) {
+			$image_src = $image_node->getAttribute( 'src' );
 		}
 
 		try {
 			$image_src = $this->upload_image( $image_src, $alt );
-		} catch ( Exception $e ) {
+
+			// Update the image src attribute.
+			$image_node->setAttribute( 'src', $image_src );
+
+			// Remove any srcset attributes.
+			if ( $image_node->hasAttribute( 'srcset' ) ) {
+				$image_node->removeAttribute( 'srcset' );
+			}
+		} catch ( Exception ) {
 			return null;
 		}
 
@@ -278,9 +486,8 @@ protected function img( DOMElement|DOMNode $element ): ?Block {
 		return new Block(
 			block_name: 'image',
 			content: sprintf(
-				'<figure class="wp-block-image"><img src="%s" alt="%s"/></figure>',
-				esc_url( $image_src ),
-				esc_attr( $alt ),
+				'<figure class="wp-block-image">%s</figure>',
+				static::get_node_html( $element ),
 			),
 		);
 	}
@@ -292,6 +499,8 @@ protected function img( DOMElement|DOMNode $element ): ?Block {
 	 * @return Block
 	 */
 	protected function ol( DOMNode $node ): Block {
+		$this->sideload_child_images( $node );
+
 		return new Block(
 			block_name: 'list',
 			attributes: [
@@ -379,7 +588,7 @@ protected function instagram_embed( string $url ): Block {
 	 * Create Instagram embed blocks.
 	 *
 	 * @param string $url The URL.
-	 * @return Blockx
+	 * @return Block
 	 */
 	protected function facebook_embed( string $url ): Block {
 		$atts = [
@@ -421,6 +630,8 @@ protected function separator(): Block {
 	 * @return Block|null
 	 */
 	protected function html( DOMNode $node ): ?Block {
+		$this->sideload_child_images( $node );
+
 		// Get the raw HTML.
 		$html = static::get_node_html( $node );
 
@@ -437,6 +648,11 @@ protected function html( DOMNode $node ): ?Block {
 	/**
 	 * Get nodes from a specific tag.
 	 *
+	 * **Note:** This method converts the node to HTML and then gets the nodes.
+	 * It cannot be use for DOMNode object modification.
+	 *
+	 * @deprecated Not used by the library. Will be removed in a future release.
+	 *
 	 * @param DOMNode $node The current DOMNode.
 	 * @param string  $tag The tag to search for.
 	 * @return DOMNodeList The raw HTML.
diff --git a/src/concerns/trait-listens-for-attachments.php b/src/concerns/trait-listens-for-attachments.php
new file mode 100644
index 0000000..88f1e5a
--- /dev/null
+++ b/src/concerns/trait-listens-for-attachments.php
@@ -0,0 +1,68 @@
+<?php
+/**
+ * Listens_For_Attachments trait file
+ *
+ * @package wp-block-converter
+ */
+
+namespace Alley\WP\Block_Converter\Concerns;
+
+/**
+ * Listens for the creation of attachments.
+ */
+trait Listens_For_Attachments {
+	/**
+	 * The attachment IDs created during the conversion.
+	 *
+	 * @var array<int>
+	 */
+	protected array $created_attachment_ids = [];
+
+	/**
+	 * Retrieve the attachment IDs created during the conversion.
+	 *
+	 * @return array<int>
+	 */
+	public function get_created_attachment_ids(): array {
+		return $this->created_attachment_ids;
+	}
+
+	/**
+	 * Assign a parent post ID to the created attachments.
+	 *
+	 * @param int $parent_post_id Parent post ID.
+	 */
+	public function assign_parent_to_attachments( int $parent_post_id ): void {
+		foreach ( $this->get_created_attachment_ids() as $attachment_id ) {
+			wp_update_post( [
+				'ID'          => $attachment_id,
+				'post_parent' => $parent_post_id,
+			] );
+		}
+	}
+
+	/**
+	 * Listen for the creation of attachments.
+	 */
+	public function listen_for_attachment_creation(): void {
+		$this->created_attachment_ids = [];
+
+		add_action( 'add_attachment', [ $this, 'track_attachment_creation' ] );
+	}
+
+	/**
+	 * Detach the attachment creation listener.
+	 */
+	public function detach_attachment_creation_listener(): void {
+		remove_action( 'add_attachment', [ $this, 'track_attachment_creation' ] );
+	}
+
+	/**
+	 * Track the creation of an attachment.
+	 *
+	 * @param int $attachment_id Attachment ID.
+	 */
+	public function track_attachment_creation( int $attachment_id ): void {
+		$this->created_attachment_ids[] = $attachment_id;
+	}
+}
diff --git a/src/helpers.php b/src/helpers.php
index 448ac84..5d0cba3 100644
--- a/src/helpers.php
+++ b/src/helpers.php
@@ -71,14 +71,16 @@ function create_or_get_attachment_from_url( string $src, array $args = [], strin
 	update_post_meta( $attachment_id, $meta_key, $src );
 
 	$postarr = [
-		'post_content' => $args['description'] ?? null,
-		'post_excerpt' => $args['caption'] ?? null,
-		'post_title'   => $args['title'] ?? null,
-		'meta_input'   => array_merge(
-			(array) ( $args['meta'] ?? [] ),
-			[
-				'_wp_attachment_image_alt' => $args['alt'] ?? null,
-			],
+		'post_content' => $args['description'] ?? '',
+		'post_excerpt' => $args['caption'] ?? '',
+		'post_title'   => $args['title'] ?? '',
+		'meta_input'   => array_filter(
+			array_merge(
+				(array) ( $args['meta'] ?? [] ),
+				[
+					'_wp_attachment_image_alt' => $args['alt'] ?? null,
+				],
+			),
 		),
 	];
 
diff --git a/tests/feature/BlockConverterTest.php b/tests/feature/BlockConverterTest.php
index 14ad854..d3b38e5 100644
--- a/tests/feature/BlockConverterTest.php
+++ b/tests/feature/BlockConverterTest.php
@@ -12,17 +12,17 @@
 use DOMNode;
 use Mantle\Testing\Concerns\Prevent_Remote_Requests;
 use Mantle\Testkit\Test_Case;
+use Mantle\Support\Str;
+use Mantle\Testing\Concerns\Refresh_Database;
 use PHPUnit\Framework\Attributes\DataProvider;
-use PHPUnit\Framework\Attributes\Group;
 
 use function Mantle\Testing\mock_http_response;
 
 /**
  * Test case for Block Block_Converter Module.
  */
-#[Group( 'block' )]
 class BlockConverterTest extends Test_Case {
-	use Prevent_Remote_Requests;
+	use Prevent_Remote_Requests, Refresh_Database;
 
 	protected function setUp(): void {
 		parent::setUp();
@@ -31,6 +31,11 @@ protected function setUp(): void {
 			'https://publish.twitter.com/oembed?maxwidth=500&maxheight=750&url=https%3A%2F%2Ftwitter.com%2Falleyco%2Fstatus%2F1679189879086018562&dnt=1&format=json' => mock_http_response()->with_json( '{"url":"https:\/\/twitter.com\/alleyco\/status\/1679189879086018562","author_name":"Alley","author_url":"https:\/\/twitter.com\/alleyco","html":"\u003Cblockquote class=\"twitter-tweet\" data-width=\"500\" data-dnt=\"true\"\u003E\u003Cp lang=\"en\" dir=\"ltr\"\u003EWe’re a full-service digital agency with the foresight, perspective, and grit to power your brightest ideas and build solutions for your most evasive problems. Learn more about our services here:\u003Ca href=\"https:\/\/t.co\/8zZ5zP1Oyc\"\u003Ehttps:\/\/t.co\/8zZ5zP1Oyc\u003C\/a\u003E\u003C\/p\u003E&mdash; Alley (@alleyco) \u003Ca href=\"https:\/\/twitter.com\/alleyco\/status\/1679189879086018562?ref_src=twsrc%5Etfw\"\u003EJuly 12, 2023\u003C\/a\u003E\u003C\/blockquote\u003E\n\u003Cscript async src=\"https:\/\/platform.twitter.com\/widgets.js\" charset=\"utf-8\"\u003E\u003C\/script\u003E\n\n","width":500,"height":null,"type":"rich","cache_age":"3153600000","provider_name":"Twitter","provider_url":"https:\/\/twitter.com","version":"1.0"}' ),
 			'https://www.tiktok.com/oembed?maxwidth=500&maxheight=750&url=https%3A%2F%2Fwww.tiktok.com%2F%40atribecalledval%2Fvideo%2F7348705314746699054&dnt=1&format=json' => mock_http_response()->with_json( '{"version":"1.0","type":"video","title":"Andre 3000 performing at Luna Luna was such an incredible night. I will never forget this night. #losangeles #andre3000 #fyp #foryou #foryoupage ","author_url":"https://www.tiktok.com/@atribecalledval","author_name":"Valeria Cardona","width":"100%","height":"100%","html":"<blockquote class=\"tiktok-embed\" cite=\"https://www.tiktok.com/@atribecalledval/video/7348705314746699054\" data-video-id=\"7348705314746699054\" data-embed-from=\"oembed\" style=\"max-width:605px; min-width:325px;\"> <section> <a target=\"_blank\" title=\"@atribecalledval\" href=\"https://www.tiktok.com/@atribecalledval?refer=embed\">@atribecalledval</a> <p>Andre 3000 performing at Luna Luna was such an incredible night. I will never forget this night. <a title=\"losangeles\" target=\"_blank\" href=\"https://www.tiktok.com/tag/losangeles?refer=embed\">#losangeles</a> <a title=\"andre3000\" target=\"_blank\" href=\"https://www.tiktok.com/tag/andre3000?refer=embed\">#andre3000</a> <a title=\"fyp\" target=\"_blank\" href=\"https://www.tiktok.com/tag/fyp?refer=embed\">#fyp</a> <a title=\"foryou\" target=\"_blank\" href=\"https://www.tiktok.com/tag/foryou?refer=embed\">#foryou</a> <a title=\"foryoupage\" target=\"_blank\" href=\"https://www.tiktok.com/tag/foryoupage?refer=embed\">#foryoupage</a> </p> <a target=\"_blank\" title=\"♬ I swear, I Really Wanted To Make A\" href=\"https://www.tiktok.com/music/I-swear-I-Really-Wanted-To-Make-A-Rap-Album-But-This-Is-Literally-The-Way-The-Wind-Blew-Me-This-Time-7302364812792547330?refer=embed\">♬ I swear, I Really Wanted To Make A \"Rap\" Album But This Is Literally The Way The Wind Blew Me This Time - André 3000</a> </section> </blockquote> <script async src=\"https://www.tiktok.com/embed.js\"></script>","thumbnail_width":576,"thumbnail_height":1024,"thumbnail_url":"https://p19-pu-sign-useast8.tiktokcdn-us.com/obj/tos-useast5-p-0068-tx/afac3ae6ea3343c890e12e3cbbca1218_1711003872?lk3s=b59d6b55&nonce=81617&refresh_token=bf81ce66fb4d648cbd499791f37a6354&x-expires=1722110400&x-signature=tpTiBYwvSXjjAEgNRU2F%2BUAz7jo%3D&shp=b59d6b55&shcp=-","provider_url":"https://www.tiktok.com","provider_name":"TikTok","author_unique_id":"atribecalledval","embed_product_id":"7348705314746699054","embed_type":"video"}' ),
 		] );
+
+		// Delete all uploaded files between tests.
+		$dir = wp_upload_dir();
+
+		shell_exec( "rm -rf {$dir['path']}/*" );
 	}
 
 	#[DataProvider( 'converter_data_provider' )]
@@ -93,6 +98,51 @@ public static function converter_data_provider() {
 		];
 	}
 
+	#[DataProvider( 'image_dataprovider' )]
+	public function test_image( string $html, string $expected ) {
+		$this->fake_request( 'https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png' )
+			->with_file( __DIR__ . '/../fixtures/image.png' );
+
+		$converter = new Block_Converter( $html );
+		$block     = $converter->convert();
+
+		$this->assertEquals( $expected, $block );
+
+		$this->assertCount( 1, $converter->get_created_attachment_ids() );
+		$this->assertRequestSent( 'https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png', 1 );
+	}
+
+	public static function image_dataprovider(): array {
+		$url = wp_upload_dir()['url'];
+
+		return [
+			'image wrapped with figure/a' => [
+				'<figure class="wp-block-image size-large"><a href="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a></figure>',
+				'<!-- wp:image --><figure class="wp-block-image"><a href="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a></figure><!-- /wp:image -->'
+			],
+			'image wrapped with figure/a with caption' => [
+				'<figure class="wp-block-image size-large"><a href="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a><figcaption>Image caption</figcaption></figure>',
+				'<!-- wp:image --><figure class="wp-block-image"><a href="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a><figcaption>Image caption</figcaption></figure><!-- /wp:image -->'
+			],
+			'image wrapped with anchor' => [
+				'<a href="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a>',
+				'<!-- wp:image --><figure class="wp-block-image"><a href="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a></figure><!-- /wp:image -->',
+			],
+			'image wrapped with paragraph' => [
+				'<p>Content to migrate <img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></p>',
+				'<!-- wp:paragraph --><p>Content to migrate <img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></p><!-- /wp:paragraph -->'
+			],
+			'image wrapped with paragraph and anchor' => [
+				'<p>Content to migrate <a href="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a></p>',
+				'<!-- wp:paragraph --><p>Content to migrate <a href="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png"><img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></a></p><!-- /wp:paragraph -->'
+			],
+			'image not wrapped' => [
+				'<img decoding="async" loading="lazy" width="786" height="672" src="https://alley.com/wp-content/uploads/2022/01/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962">',
+				'<!-- wp:image --><figure class="wp-block-image"><img decoding="async" loading="lazy" width="786" height="672" src="' . $url . '/Screen-Shot-2022-01-19-at-2.51.37-PM.png" alt="" class="wp-image-5962"></figure><!-- /wp:image -->',
+			],
+		];
+	}
+
 	public function test_convert_with_empty_paragraphs_of_arbitrary_length_to_block() {
 		$arbitraryNewLines = str_repeat( "\n\r", mt_rand( 1, 1000) );
 		$arbitrarySpaces = str_repeat( " ", mt_rand( 1, 1000 ) );
diff --git a/tests/fixtures/image.png b/tests/fixtures/image.png
new file mode 100644
index 0000000..99eb4a8
Binary files /dev/null and b/tests/fixtures/image.png differ