diff --git a/docs/hooks.md b/docs/hooks.md
index 10f04745b..3718c9b6d 100644
--- a/docs/hooks.md
+++ b/docs/hooks.md
@@ -63,6 +63,13 @@ Available Hooks
     To use this hook, pass a callback via `$options['complete']` when calling
     `WpOrg\Requests\Requests\request_multiple()`.
 
+* **`requests.failed`**
+
+    Alter/Inspect transport or response parsing exception before it is returned to the user.
+
+    Parameters: `WpOrg\Requests\Exception|WpOrg\Requests\Exception\InvalidArgument &$exception`, `string $url`, `array $headers`, `array|string $data`,
+    `string $type`, `array $options`
+
 * **`curl.before_request`**
 
     Set cURL options before the transport sets any (note that Requests may
diff --git a/src/Exception.php b/src/Exception.php
index ef8d0ff43..8e7de2fde 100644
--- a/src/Exception.php
+++ b/src/Exception.php
@@ -31,6 +31,13 @@ class Exception extends PHPException {
 	 */
 	protected $data;
 
+	/**
+	 * Whether the exception was already passed to the requests.failed hook or not
+	 *
+	 * @var boolean
+	 */
+	public $failed_hook_handled = false;
+
 	/**
 	 * Create a new exception
 	 *
diff --git a/src/Exception/InvalidArgument.php b/src/Exception/InvalidArgument.php
index 0d6d88095..99cce5216 100644
--- a/src/Exception/InvalidArgument.php
+++ b/src/Exception/InvalidArgument.php
@@ -19,6 +19,13 @@
  */
 final class InvalidArgument extends InvalidArgumentException {
 
+	/**
+	 * Whether the exception was already passed to the requests.failed hook or not
+	 *
+	 * @var boolean
+	 */
+	public $failed_hook_handled = false;
+
 	/**
 	 * Create a new invalid argument exception with a standardized text.
 	 *
diff --git a/src/Requests.php b/src/Requests.php
index 9390800b6..5937b90cf 100644
--- a/src/Requests.php
+++ b/src/Requests.php
@@ -465,11 +465,29 @@ public static function request($url, $headers = [], $data = [], $type = self::GE
 			$transport    = self::get_transport($capabilities);
 		}
 
-		$response = $transport->request($url, $headers, $data, $options);
+		try {
+			$response = $transport->request($url, $headers, $data, $options);
+
+			$options['hooks']->dispatch('requests.before_parse', [&$response, $url, $headers, $data, $type, $options]);
+
+			$parsed_response = self::parse_response($response, $url, $headers, $data, $options);
+		} catch (Exception $e) {
+			if ($e->failed_hook_handled === false) {
+				$options['hooks']->dispatch('requests.failed', [&$e, $url, $headers, $data, $type, $options]);
+				$e->failed_hook_handled = true;
+			}
+
+			throw $e;
+		} catch (InvalidArgument $e) {
+			if ($e->failed_hook_handled === false) {
+				$options['hooks']->dispatch('requests.failed', [&$e, $url, $headers, $data, $type, $options]);
+				$e->failed_hook_handled = true;
+			}
 
-		$options['hooks']->dispatch('requests.before_parse', [&$response, $url, $headers, $data, $type, $options]);
+			throw $e;
+		}
 
-		return self::parse_response($response, $url, $headers, $data, $options);
+		return $parsed_response;
 	}
 
 	/**
diff --git a/tests/Fixtures/TransportFailedMock.php b/tests/Fixtures/TransportFailedMock.php
new file mode 100644
index 000000000..ec22c557a
--- /dev/null
+++ b/tests/Fixtures/TransportFailedMock.php
@@ -0,0 +1,18 @@
+<?php
+
+namespace WpOrg\Requests\Tests\Fixtures;
+
+use WpOrg\Requests\Exception;
+use WpOrg\Requests\Transport;
+
+final class TransportFailedMock implements Transport {
+	public function request($url, $headers = [], $data = [], $options = []) {
+		throw new Exception('Transport failed!', 'transporterror');
+	}
+	public function request_multiple($requests, $options) {
+		throw new Exception('Transport failed!', 'transporterror');
+	}
+	public static function test($capabilities = []) {
+		return true;
+	}
+}
diff --git a/tests/Fixtures/TransportInvalidArgumentMock.php b/tests/Fixtures/TransportInvalidArgumentMock.php
new file mode 100644
index 000000000..2e606ba2b
--- /dev/null
+++ b/tests/Fixtures/TransportInvalidArgumentMock.php
@@ -0,0 +1,18 @@
+<?php
+
+namespace WpOrg\Requests\Tests\Fixtures;
+
+use WpOrg\Requests\Exception\InvalidArgument;
+use WpOrg\Requests\Transport;
+
+final class TransportInvalidArgumentMock implements Transport {
+	public function request($url, $headers = [], $data = [], $options = []) {
+		throw InvalidArgument::create(1, '$url', 'string|Stringable', gettype($url));
+	}
+	public function request_multiple($requests, $options) {
+		throw InvalidArgument::create(1, '$requests', 'array|ArrayAccess&Traversable', gettype($requests));
+	}
+	public static function test($capabilities = []) {
+		return true;
+	}
+}
diff --git a/tests/Fixtures/TransportRedirectMock.php b/tests/Fixtures/TransportRedirectMock.php
new file mode 100644
index 000000000..e6efa8b5e
--- /dev/null
+++ b/tests/Fixtures/TransportRedirectMock.php
@@ -0,0 +1,65 @@
+<?php
+
+namespace WpOrg\Requests\Tests\Fixtures;
+
+use WpOrg\Requests\Transport;
+use WpOrg\Requests\Utility\HttpStatus;
+
+final class TransportRedirectMock implements Transport {
+	public $code        = 302;
+	public $chunked     = false;
+	public $body        = '';
+	public $raw_headers = '';
+
+	private $redirected = [];
+
+	public $redirected_transport = null;
+
+	public function request($url, $headers = [], $data = [], $options = []) {
+		if (array_key_exists($url, $this->redirected)) {
+			return $this->redirected_transport->request($url, $headers, $data, $options);
+		}
+
+		$redirect_url = 'https://example.com/redirected?url=' . urlencode($url);
+
+		$text      = HttpStatus::is_valid_code($this->code) ? HttpStatus::get_text($this->code) : 'unknown';
+		$response  = "HTTP/1.0 {$this->code} $text\r\n";
+		$response .= "Content-Type: text/plain\r\n";
+		if ($this->chunked) {
+			$response .= "Transfer-Encoding: chunked\r\n";
+		}
+
+		$response .= "Location: $redirect_url\r\n";
+		$response .= $this->raw_headers;
+		$response .= "Connection: close\r\n\r\n";
+		$response .= $this->body;
+
+		$this->redirected[$url]          = true;
+		$this->redirected[$redirect_url] = true;
+
+		return $response;
+	}
+
+	public function request_multiple($requests, $options) {
+		$responses = [];
+		foreach ($requests as $id => $request) {
+			$handler              = new self();
+			$handler->code        = $request['options']['mock.code'];
+			$handler->chunked     = $request['options']['mock.chunked'];
+			$handler->body        = $request['options']['mock.body'];
+			$handler->raw_headers = $request['options']['mock.raw_headers'];
+			$responses[$id]       = $handler->request($request['url'], $request['headers'], $request['data'], $request['options']);
+
+			if (!empty($options['mock.parse'])) {
+				$request['options']['hooks']->dispatch('transport.internal.parse_response', [&$responses[$id], $request]);
+				$request['options']['hooks']->dispatch('multiple.request.complete', [&$responses[$id], $id]);
+			}
+		}
+
+		return $responses;
+	}
+
+	public static function test($capabilities = []) {
+		return true;
+	}
+}
diff --git a/tests/Requests/RequestsTest.php b/tests/Requests/RequestsTest.php
index e229ace17..f1f9dfdee 100644
--- a/tests/Requests/RequestsTest.php
+++ b/tests/Requests/RequestsTest.php
@@ -4,11 +4,15 @@
 
 use WpOrg\Requests\Exception;
 use WpOrg\Requests\Exception\InvalidArgument;
+use WpOrg\Requests\Hooks;
 use WpOrg\Requests\Iri;
 use WpOrg\Requests\Requests;
 use WpOrg\Requests\Response\Headers;
 use WpOrg\Requests\Tests\Fixtures\RawTransportMock;
+use WpOrg\Requests\Tests\Fixtures\TransportFailedMock;
+use WpOrg\Requests\Tests\Fixtures\TransportInvalidArgumentMock;
 use WpOrg\Requests\Tests\Fixtures\TransportMock;
+use WpOrg\Requests\Tests\Fixtures\TransportRedirectMock;
 use WpOrg\Requests\Tests\TestCase;
 use WpOrg\Requests\Tests\TypeProviderHelper;
 
@@ -152,6 +156,42 @@ public function testDefaultTransport() {
 		$this->assertSame(200, $request->status_code);
 	}
 
+	public function testTransportFailedTriggersRequestsFailedCallback() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport = new TransportFailedMock();
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(Exception::class);
+		$this->expectExceptionMessage('Transport failed!');
+		Requests::get('http://example.com/', [], $options);
+	}
+
+	public function testTransportInvalidArgumentTriggersRequestsFailedCallback() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport = new TransportInvalidArgumentMock();
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(InvalidArgument::class);
+		$this->expectExceptionMessage('Argument #1 ($url) must be of type string|Stringable');
+		Requests::get('http://example.com/', [], $options);
+	}
+
 	/**
 	 * Standard response header parsing
 	 */
@@ -252,6 +292,31 @@ public function testInvalidProtocolVersion() {
 		Requests::get('http://example.com/', [], $options);
 	}
 
+	/**
+	 * Check that invalid protocols are not accepted
+	 *
+	 * We do not support HTTP/0.9. If this is really an issue for you, file a
+	 * new issue, and update your server/proxy to support a proper protocol.
+	 */
+	public function testInvalidProtocolVersionTriggersRequestsFailedCallback() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport       = new RawTransportMock();
+		$transport->data = "HTTP/0.9 200 OK\r\n\r\n<p>Test";
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(Exception::class);
+		$this->expectExceptionMessage('Response could not be parsed');
+		Requests::get('http://example.com/', [], $options);
+	}
+
 	/**
 	 * HTTP/0.9 also appears to use a single CRLF instead of two.
 	 */
@@ -268,6 +333,28 @@ public function testSingleCRLFSeparator() {
 		Requests::get('http://example.com/', [], $options);
 	}
 
+	/**
+	 * HTTP/0.9 also appears to use a single CRLF instead of two.
+	 */
+	public function testSingleCRLFSeparatorTriggersRequestsFailedCallback() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport       = new RawTransportMock();
+		$transport->data = "HTTP/0.9 200 OK\r\n<p>Test";
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(Exception::class);
+		$this->expectExceptionMessage('Missing header/body separator');
+		Requests::get('http://example.com/', [], $options);
+	}
+
 	public function testInvalidStatus() {
 		$transport       = new RawTransportMock();
 		$transport->data = "HTTP/1.1 OK\r\nTest: value\nAnother-Test: value\r\n\r\nTest";
@@ -281,6 +368,25 @@ public function testInvalidStatus() {
 		Requests::get('http://example.com/', [], $options);
 	}
 
+	public function testInvalidStatusTriggersRequestsFailedCallback() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport       = new RawTransportMock();
+		$transport->data = "HTTP/1.1 OK\r\nTest: value\nAnother-Test: value\r\n\r\nTest";
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(Exception::class);
+		$this->expectExceptionMessage('Response could not be parsed');
+		Requests::get('http://example.com/', [], $options);
+	}
+
 	public function test30xWithoutLocation() {
 		$transport       = new TransportMock();
 		$transport->code = 302;
@@ -293,6 +399,52 @@ public function test30xWithoutLocation() {
 		$this->assertSame(0, $response->redirects);
 	}
 
+	public function testRedirectToExceptionTriggersRequestsFailedCallbackOnce() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport                       = new TransportRedirectMock();
+		$transport->redirected_transport = new TransportFailedMock();
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(Exception::class);
+		$this->expectExceptionMessage('Transport failed!');
+
+		$response = Requests::get('http://example.com/', [], $options);
+
+		$this->assertSame(302, $response->status_code);
+		$this->assertSame(1, $response->redirects);
+	}
+
+	public function testRedirectToInvalidArgumentTriggersRequestsFailedCallbackOnce() {
+		$mock = $this->getMockedStdClassWithMethods(['failed']);
+		$mock->expects($this->once())->method('failed');
+		$hooks = new Hooks();
+		$hooks->register('requests.failed', [$mock, 'failed']);
+
+		$transport                       = new TransportRedirectMock();
+		$transport->redirected_transport = new TransportInvalidArgumentMock();
+
+		$options = [
+			'hooks'     => $hooks,
+			'transport' => $transport,
+		];
+
+		$this->expectException(InvalidArgument::class);
+		$this->expectExceptionMessage('Argument #1 ($url) must be of type string|Stringable');
+
+		$response = Requests::get('http://example.com/', [], $options);
+
+		$this->assertSame(302, $response->status_code);
+		$this->assertSame(1, $response->redirects);
+	}
+
 	public function testTimeoutException() {
 		$options = ['timeout' => 0.5];
 		$this->expectException(Exception::class);